CN110407916A - A kind of plain five peptide analogues of insect suppression corporal allata of the urea structure containing formyl and its application - Google Patents
A kind of plain five peptide analogues of insect suppression corporal allata of the urea structure containing formyl and its application Download PDFInfo
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- CN110407916A CN110407916A CN201910717490.XA CN201910717490A CN110407916A CN 110407916 A CN110407916 A CN 110407916A CN 201910717490 A CN201910717490 A CN 201910717490A CN 110407916 A CN110407916 A CN 110407916A
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- 241000238631 Hexapoda Species 0.000 title abstract description 22
- 241000288283 Allata Species 0.000 title abstract description 16
- 108090000765 processed proteins & peptides Proteins 0.000 title abstract description 15
- 230000001629 suppression Effects 0.000 title abstract description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title abstract description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- -1 cyano, hydroxyl Chemical class 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 241000500437 Plutella xylostella Species 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical class [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical class FC(F)(F)* 0.000 claims abstract description 3
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 150000001555 benzenes Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 7
- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 claims description 7
- 241001674044 Blattodea Species 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 239000007790 solid phase Substances 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- ZYMCBJWUWHHVRX-UHFFFAOYSA-N (4-nitrophenyl)-phenylmethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=CC=C1 ZYMCBJWUWHHVRX-UHFFFAOYSA-N 0.000 claims description 2
- GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- QUBJDMPBDURTJT-UHFFFAOYSA-N 3-chlorothiophene Chemical compound ClC=1C=CSC=1 QUBJDMPBDURTJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 26
- 230000002401 inhibitory effect Effects 0.000 abstract description 11
- 238000011161 development Methods 0.000 abstract description 8
- 230000018109 developmental process Effects 0.000 abstract description 8
- 239000003630 growth substance Substances 0.000 abstract description 6
- 230000012010 growth Effects 0.000 abstract description 5
- 239000002917 insecticide Substances 0.000 abstract description 3
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 23
- 229930014550 juvenile hormone Natural products 0.000 description 16
- 239000002949 juvenile hormone Substances 0.000 description 16
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 6
- 102000004196 processed proteins & peptides Human genes 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000012544 monitoring process Methods 0.000 description 5
- 239000000575 pesticide Substances 0.000 description 5
- 241000238674 Blaberidae Species 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000238791 Diploptera punctata Species 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 230000003054 hormonal effect Effects 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 101100164120 Caenorhabditis elegans asb-2 gene Proteins 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 101000738322 Homo sapiens Prothymosin alpha Proteins 0.000 description 2
- 108090000189 Neuropeptides Proteins 0.000 description 2
- 102000003797 Neuropeptides Human genes 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 102100037925 Prothymosin alpha Human genes 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 150000002611 lead compounds Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000003750 lower gastrointestinal tract Anatomy 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000029052 metamorphosis Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000004885 tandem mass spectrometry Methods 0.000 description 2
- SJVFAHZPLIXNDH-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 SJVFAHZPLIXNDH-QFIPXVFZSA-N 0.000 description 1
- CBPJQFCAFFNICX-IBGZPJMESA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CC(C)C)C(O)=O)C3=CC=CC=C3C2=C1 CBPJQFCAFFNICX-IBGZPJMESA-N 0.000 description 1
- LDWBQGACJJOIKA-RHEFHGCGSA-N (2s)-2-[[(2s)-6-amino-2-[[(2s,3r)-2-[[(2s,3r)-2-[[(2s)-2,6-diaminohexanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoic acid Chemical compound NCCCC[C@H](N)C(=O)N[C@@H]([C@H](O)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(O)=O LDWBQGACJJOIKA-RHEFHGCGSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- NDKDFTQNXLHCGO-UHFFFAOYSA-N 2-(9h-fluoren-9-ylmethoxycarbonylamino)acetic acid Chemical compound C1=CC=C2C(COC(=O)NCC(=O)O)C3=CC=CC=C3C2=C1 NDKDFTQNXLHCGO-UHFFFAOYSA-N 0.000 description 1
- 101710167064 Allatostatins Proteins 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 150000008574 D-amino acids Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000409991 Mythimna separata Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 210000002251 corpora allata Anatomy 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000000087 hemolymph Anatomy 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000004920 integrated pest control Methods 0.000 description 1
- 229930191400 juvenile hormones Natural products 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NWKYZYGOSPOKDY-UHFFFAOYSA-N n,n-dimethylformamide;pyridine Chemical compound CN(C)C=O.C1=CC=NC=C1 NWKYZYGOSPOKDY-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000001719 neurosecretory cell Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000012207 quantitative assay Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Peptides Or Proteins (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention belongs to a kind of plain five peptide analogues of the insect of technical field of insecticide more particularly to urea structure containing formyl suppression corporal allata and its applications, propose a kind of compound shown in formula A, have such as flowering structure:
Description
Technical field
The invention belongs to the insects of technical field of insecticide more particularly to a kind of urea structure containing formyl to press down corporal allata element pentapeptide
Analog and its application
Background technique
Along with the use of traditional pesticide, 3R (resistance, rampant again and residual) problem gradually shows.Traditional pesticide is to green
Pesticide direction is developed.Wherein, insect growth regulator, IGR (IGRs) is because it is with the spies such as efficient, highly selective and environmental-friendly
Point, plays an important role in integrated pest control.Insect neuropeptide is by insect brain internal specific neurosecretory cell week
A kind of active small peptide for synthesizing to phase property, secreting and transmitted by nerve or hemolymph, influences the growth, development, metamorphosis of insect
Etc. physiology courses, it is considered to be a kind of potential insect growth regulator, IGR.
Suppression corporal allata plain (Allatostatins, abbreviation ASTs) is one kind earliest from Pacific Ocean Blaberidae
(Diploptera punctata) internal isolated insect neuropeptide.By acting on insect corporal allata (CA), inhibit
The biosynthesis of corpus allatum hormone (Juvenile Hormone JH), and then insectean metamorphosis development is influenced, eventually lead to insect
Death is a kind of potential insect growth regulator, IGR.Compared with other bioactive substances, suppression corporal allata element has apparent excellent
Point: (1) activity is high；(2) selectivity is strong, has very strong inhibiting effect to the CA of target insect；(3) environmental-friendly, ASTs degradation
Amino acid is mainly generated, safety is good, to people and animals' low toxicity；(4) compared with other active peptides, ASTs structure is simple, is easy to be transformed.
Therefore, people have carried out a large amount of research to AST.ASTs is prevalent in various insects, it is common as blattaria, drosophila,
Mosquito, mythimna separata and locust etc..ASTs has the function of inhibiting CA synthesis JH, while also can inhibit anterior intestine, middle intestines, hindgut muscle
Shrink the development with orthopter ovary；It can also inhibit the contraction etc. of muscle in the organs such as heart, dorsal blood vessel and fallopian tubal.
It is widely distributed in insect bodies to press down corporal allata element, has and efficiently inhibits juvenile hormone biological synthetic functional.However
Defect ASTs intrinsic in the intracorporal metabolic inactivation mechanism of insect and native peptides, limits ASTs and is done harm to directly as pesticide
Worm prevention and treatment.In order to overcome many disadvantages of natural suppression corporal allata element, many researchers carry out structural modification and transformation to ASTs.
The polypeptide that ASTs is made of 6-18 amino acid residue, in order to determine the active part in conjunction with receptor, science
Family using shorten peptide chain method the functional area of AST analog has been determined --- " core pentapeptide (YXFGLa) ".1991
Year, Stay etc. is with 4 (DRLYSFGL-NH of Dippu-AST2) it is that guide devises 2 segment peptide 4a (LYSFGL-NH2) and 4b
(YSFGL-NH2), biological activity test the result shows that, although 4a and 4b inhibit the ability ratio Dippu-AST 4 of juvenile hormone to divide
1 and 2 orders of magnitude, IC are not reduced50Value is respectively 10-8Mol/L and 10-7Mol/L, but still keep inhibiting well
Activity, thus it is speculated that segment Tyr-Ser-Phe-Gly-Leu-NH2It is to have to inhibit the active most short sequence of juvenile hormone biosynthesis.
The same year, Pratt etc. are that guide devises a series of with ASB 2 (i.e. Dippu-AST 2, AYSYVSEYKRLPVYNFGLa)
Disconnected peptide, the C- end part (YNFGLa) that discovery retains ASB 2 can maintain preferably to inhibit juvenile hormone biosynthesis active, if lacking
Lose the region or C-terminal Leu-NH2Amidation is gone, then loses inhibitory activity.On this basis, Hayes etc. utilizes amino acid substitution
Method determine conservative amino acid residues, L-Ala and D- amino acid is replaced into each amino acid in core pentapeptide one by one, determine
Tyr in core pentapeptide4、Phe6、Gly7And Leu8Side chain have larger impact to bioactivity, wherein Leu8Side chain replace
Base is mostly important, followed by Phe6Side-chain radical；Meanwhile after being replaced with D amino acids, Ser is found5、Phe6And Leu8's
The chiral bioactivity with Dippu-AST 4 has close contact.
Piulachs etc. with Groton bug Blattella germanica BLAST 2 (DRLYSFGLamide, i.e.,
Dippu-AST 5) it is lead compound, according to the enzymatic hydrolysis site Leu of Dippu-AST 53-Tyr4, devise methylene ammonia (-
CH2NH-) and methylene ketone (- COCH2-) replace analog PTMA and PTMB, biological activity test as the result is shown: analog
PTMA and PTMB inhibits Groton bug corporal allata synthesis juvenile hormone activity to be slightly below native peptides BLAST 2 in vitro,
But living body activity is much higher than native peptides BLAST 2.
Nachman etc. replaces Dippu-AST on the Research foundation of Hayes, with unnatural amino acid Aic, Cpa and Bzd
6 Phe6、Gly7Amino acid residue devises 5 peptidomimetics.Bioactivity is the results show that 1 (ED of analog50=3.2nmol/L)
Activity with 6 (ED of lead compound Dippu-AST50=2.3nmol/L) activity quite, illustrate utilize unnatural amino acid
Aic replaces Phe6The activity of ASTs can be kept, while can be improved resistance to enzymolysis ability.And 2 (ED of analog50=0.16 μ
Mol/L), 3 (ED of analog50=0.80 μm of ol/L), analog 4a (ED50=10 μm of ol/L) and 4b (ED50=0.1-10 μ
Mol/L activity) reduces several orders of magnitude, introduces Cpa and Bzd and increases steric hindrance, increases the rigidity of molecule, biology
Activity substantially reduces, thus it is speculated that Gly7Site space need to keep certain molecular flexibility, while being not easy to draw in design synthesis process
Enter biggish group.Benzenpropanoic acid is also introduced into " core pentapeptide " by Nachman etc., has synthesized analog AST (b) φ 2, in vitro
Active testing is the results show that the more natural Dippu-AST 5 of the activity of AST (b) φ 2 is compared to reducing 3 orders of magnitude, but it is in blood
Metabolic stability in lymph, brain and hindgut is greatly improved.
Inventor has been devoted to AST structural modification also in recent years to find the high-activity compound of structure novel, has
It closes invention and has applied for related patents, referring to patent document 1-5.
Existing technical literature
Patent document
Patent document 1:CN 101519430A；
Patent document 2:CN 101519431A；
Patent document 3:CN 101519432A；
Patent document 4:CN 101519433A；
Patent document 5:CN102093251A；
Patent document 6:CN104693274B.
Summary of the invention
Technical problems to be solved by the inivention
The object of the present invention is to provide have the good AST analog for inhibiting juvenile hormone activity.
Method for solving technical problem
In view of the above-mentioned problems, the present invention presses down corporal allata element analog H17 based on high activity, substituted benzene is introduced in N-terminal
Ring and substituted thiophene ring, while introducing acyl group urea structure and replacing ethylene linkage and amido bond, a kind of compound shown in formula A is proposed,
It has such as flowering structure:
Wherein:
In formula A, R is aromatic rings or substituted aroma ring；
Substituent group is monosubstituted or polysubstituted halogen, nitro, trifluoromethyl, cyano, hydroxyl, methyl or methoxy.
A kind of embodiment is, in formula A, R is phenyl ring or substituted benzene ring, thiphene ring or substituted thiophene ring.Preferably, R is
Phenyl, 4- nitrobenzophenone, 2- fluorophenyl, 4- fluorophenyl, 2- chlorphenyl, 4- chlorphenyl, 4- bromophenyl, 2,6- difluorophenyl, 2,
6- dichlorophenyl, thienyl, 3- first thienyl, 3- chlorothiophene base, 5- chlorothiophene base.
A kind of embodiment is that compound is any one compound represented by following (1) to (7):
(1) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is hydrogen；
(2) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is 4- nitro；
(3) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is 4- fluorine；
(4) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is 4- chlorine；
(5) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is 4- bromine；
(6) in formula A, R is substituted thiophene ring, and the substituent group in thiphene ring is 3- methyl；
(7) in formula A, R is substituted thiophene ring, and the substituent group in thiphene ring is 3- chlorine.
According to the second aspect of the invention, a kind of preparation method of above compound is provided, wherein use the organic conjunction of solid phase
It is prepared at method.
According to the third aspect of the invention we, a kind of application of above compound in cockroach prevention and cure is provided.
According to the fourth aspect of the invention, a kind of application of above compound in diamondback moth prevention and treatment is provided.
According to the fifth aspect of the invention, a kind of pharmaceutical composition of above compound is provided, wherein it further include carrier,
Wherein, the carrier is selected from diluent, excipient, filler, adhesive, wetting agent, sorbefacient, surfactant, profit
One or more of lubrication prescription, stabilizer.
Beneficial effects of the present invention
The present invention compared with early-stage study, its main feature is that: to there is preferably five peptide analogues of active suppression corporal allata element early period
H17 is guide, is transformed for enzymatic hydrolysis site, replaces ethylene linkage and amido bond by introducing acyl group urea structure, while drawing in N-terminal
Enter substituted benzene ring and substituted thiophene ring, obtained it is a kind of there is the good AST analog for inhibiting juvenile hormone activity, wherein A6 and
The isolated activity of A7 compound is much better than guide H17.Such compound in vitro can obviously inhibit cockroach juvenile hormone
Biosynthesis, and then influence insect growth and development.Insecticidal activity primary dcreening operation shows that such compound has certain inhibition small
The activity of diamond-back moth larva growth, meets the feature of insect growth regulator, IGR, has further application and development to be worth.
From the description of following exemplary embodiment, further characteristic of the invention will become obvious.
Specific embodiment
An embodiment of the disclosure is specifically described below, but the disclosure is not limited to this.
Formula A compound provided by the present invention, obtain according to Solid-phase organic synthesis method (bibliography: Chan WG,
White PD.Fmoc solid phase peptide synthesis A Practical Approach,Oxford
University Press,2000；pp.9-74.).
In Vitro Bioassay experiment of the invention is using the gas-chromatography tandem mass spectrometry (GC-MS/MS) for opening vibration roc et al.
(Kai,Z.P.；Yin,Y.；Zhang,Z.R.；Huang,J.；Tobe,S.S.；Chen,S.S., A rapid
quantitative assay for juvenile hormones and intermediates in the
biosynthetic pathway using gas chromatography tandem mass spectrometry.J
Chromatogr A 2018,1538,67-74.), it tests formula A compound and inhibits Pacific Ocean Blaberidae (Diploptera
Punctata) the isolated activity of juvenile hormone synthesis.
Insecticidal activity screening technique to diamondback moth larvae of the invention is according to for " pesticide bioactivity testing standard operates
Specification -- insecticide volume " (Gu Baogen, Liu Xue chief editor, Chemical Industry Press, 2016), using leaf dipping method (SOP-SC-
2052) evaluation of diamondback moth larvae inhibitory activity is carried out.
It when needed can be with for the drug containing prevention and treatment cockroach and diamondback moth that formula A compound is active constituent
Acceptable carrier in one or more pesticidal preparations is added, the carrier includes diluent conventional in pesticidal preparations, figuration
Agent, filler, adhesive, wetting agent, sorbefacient, surfactant, lubricant, stabilizer etc..The agent of manufactured drug
Type is also multiplicity, can be pulvis, microemulsion, bait formulation, microcapsule formulations, missible oil etc..
Embodiment
By embodiment, the present invention will be described in more detail, but the present invention is not limited to following embodiments.It should be noted that only
Otherwise special declaration, " part " expression " mass parts ".
Embodiment 1
The preparation of formula A compound is prepared according to the method for Solid-phase synthesis peptides.
By taking compound A1 as an example, preparation method is as follows:
(1) resin activated: to weigh 440mg Rink Amide-AM resin, activate 3h with 5mL DCM, 20% piperazine is added
The cutting of pyridine DMF solution 20min, DMF and DCM are respectively washed 3 times, the monitoring reaction of Kaiser ' s reagent.
(2) it meets Leu: being added Fmoc-Leu-OH (3 times of equivalents), HBTU (3 times of equivalents), HOBt (3 times of equivalents), DIEA (6
Times equivalent), it is dissolved in 5mLDMF, 2h is stirred at room temperature, sloughs reaction solution, DMF and DCM are respectively washed 3 times, and the monitoring of Kaiser ' s reagent is anti-
It answers.After 20% Piperidine/DMF solution cutting 20min is added, DMF washes 3 times.
(3) it meets Gly: being added Fmoc-Gly-OH (3 times of equivalents), HBTU (3 times of equivalents), HOBt (3 times of equivalents), DIEA (6
Times equivalent), it is dissolved in 5mLDMF, 2h is stirred at room temperature, sloughs reaction solution, DMF and DCM are respectively washed 34 times, and the monitoring of Kaiser ' s reagent is anti-
It answers.After 20% Piperidine/DMF solution cutting 20min is added, DMF washes 3 times.
(4) it meets Phe: being added Fmoc-Phe-OH (3 times of equivalents), HBTU (3 times of equivalents), HOBt (3 times of equivalents), DIEA (6
Times equivalent), it is dissolved in 5mLDMF, 2h is stirred at room temperature, sloughs reaction solution, DMF and DCM are respectively washed 3 times, and the monitoring of Kaiser ' s reagent is anti-
It answers.After 20% Piperidine/DMF solution cutting 20min is added, DMF washes 3 times.
(5) preparation of benzoyl isocyanate: taking the round-bottomed flask of 100mL, and 1, the 2- dichloroethanes of 30mL is added, point
The substituted amide of 3 equivalents and the oxalyl chloride of 3.6 equivalents are not added, is heated to reflux 12h.Air-distillation obtains benzoyl isocyanic acid
Ester.
(6) benzoyl isocyanate is reacted with Gly (tBu): taking the round-bottomed flask of 100mL, 1, the 2- dichloro of 30mL is added
Ethane by the benzoyl isocyanate of preparation and Gly (tBu), reacts at room temperature 3h as solvent, after reaction plus 0.2 equivalent
Trifluoroacetic acid, obtain intermediate 1.
(7) connect intermediate 1: intermediate 1 (3 times of equivalents), HBTU (3 times of equivalents), HOBt (3 times of equivalents), (6 times are worked as DIEA
Amount), it is dissolved in 5mLDMF, 2h is stirred at room temperature, sloughs reaction solution, DMF and DCM are respectively washed 3 times, the monitoring reaction of Kaiser ' s reagent.
(8) it cuts, sloughs Side chain protective group: resin addition 250mg phenol, 0.5ml water, 0.5ml thioanisole,
2.5h is stirred at room temperature in 9.0mLTFA, and filtering removes TFA, and 30mL anhydrous ether is added, and 3000r/min is centrifuged 5min, obtains white
Precipitating, vacuum drying, Mass Spectrometer Method.
(9) crude product is isolated and purified with HPLC.After the solution of collection sloughs acetonitrile, it is lyophilized and net product is made.Chromatographic column is
C18 semi-preparative column.
Compound A2-A13 is prepared according to the above method.
Formula A compound structure, high resolution mass spectrum data, physicochemical character and activity data are listed in table 1,
Table 1, structure, high resolution mass spectrum data (HRMS) and the physical behavior and activity data of formula A compound
In vitro inhibitory activity of 2 the compounds of this invention of embodiment to juvenile hormone biosynthesis in the Blaberidae body of the Pacific Ocean
The present invention is using the GC-MS/MS bioassay method (reference: Kai, Z.P. for opening vibration roc et al.；Yin,Y.；
Zhang,Z.R.；Huang,J.；Tobe,S.S.；Chen,S.S.J.Chromatogr.A.2018,1538,67).To just plumage
The female insect of change is collected, until dissection obtains corporal allata after the 7th day.Target compound is made into the mother liquor of 10mmol/L, according to
The secondary measurement liquid for being diluted to 1mmol/L, 0.1mmol/L, 0.01mmol/L, 0.001mmol/L and 0.0001mmol/L.It uses again
The liquid-transfering gun of 1-10uL takes the measurement liquid of 10uL various concentration to be added to the centrifuge tube of the 1.5mL containing 990uL M199 culture medium
In, be sufficiently mixed uniformly after, it is obtained to concentration be respectively 0.01mmol/L, 0.001mmol/L, 0.0001mmol/L,
0.00001mmol/L and 0.000001mmol/L.The medical fluid for measuring 100uL configuration is added in cuvette, in each tubule
A corporal allata is placed, 8-16 repetition is arranged in each concentration.Cuvette is protected from light 3 hours of incubated at room temperature.Culture finishes
Afterwards, with the juvenile hormone in the n-hexane extraction culture medium of 200uL, citronellol is as internal standard.Not with the measurement of GC-MS/MS method
With JH content in cuvette under compound various concentration.It is carried out inhibiting juvenile hormone biosynthesis with GraphPad Prism5
Active IC50 value calculates.Raw survey the results are shown in Table 1 to formula A compound in vitro.
Table 1 the result shows that: formula A compound can obviously inhibit Pacific Ocean Blaberidae (Diploptera punctata) protect
The biosynthesis of young hormone, the isolated activity of A1, A2, A4, A6, A7, A11 and A13 are better than guide H17, wherein analog A6
Reach nanomole rank with the isolated activity of A7, the bioactivity of A7 analog is 26 times of guide H17.Structure-activity relationship shows:
(1) it introduces urea linkage and is conducive to active raising.(2) N-terminal be phenyl ring, 4 halogen atoms replace compound activity compared with
Height, wherein 4-Br compound activity is best, and monosubstituted activity is better than disubstituted activity.(3) N-terminal is thiphene ring, and 5 substitutions are lived
Property is preferable.In conclusion A7 have well inhibit juvenile hormone biosynthesis activity, have as cockroach controlling agent carry out into
The value of one step application and development.
The part of compounds of the invention of embodiment 3 is under 200mg/L concentration to the activity such as claim of diamondback moth larvae
Application of five peptide analogues of any a kind of insect suppression corporal allata element of 1-3 in diamondback moth prevention and treatment.Diamondback moth is killed
Worm method for screening active ingredients is as follows: using leaf dipping method；It carries out under 200mg/L concentration, the primary dcreening operation of A6, A7 to diamondback moth insecticidal activity；
Raw medicine is dissolved with a small amount of DMF, is then diluted with 0.05% TritonX-100 aqueous solution.Each concentration is repeated 4 times,
Blank control is arranged in 30 test worms of each repetition；The cabbage leaves of growth always are chosen, 5s in the medical fluid of 200mg/L is immersed in,
After interior dries 2 hours, it is put into the training culture dish that diameter is 9cm, accesses 2 age of diamondback moth Initial instar larvae of the same size.
96 as a child inspection result and calculated the correction death rate；Polypide is touched with small writing brush or tweezers, is unable to normal activity, that is, is considered as dead
It dies.Analog A6, A7 the results are shown in Table 2.
Table 2, analog A6, A7 kill diamondback moth bioactivity (%) under 200mg/L concentration
Table 2 the result shows that: high activity inhibit juvenile hormone biosynthesis suppression corporal allata element analog A6, A7, to pickles
2 instar larvae of moth shows certain inhibitory activity, has the potential application Development volue as diamondback moth growth regulator.
This embodiment is merely preferred embodiments of the present invention, but scope of protection of the present invention is not limited thereto,
In the technical scope disclosed by the present invention, any changes or substitutions that can be easily thought of by anyone skilled in the art,
It should be covered by the protection scope of the present invention.Therefore, protection scope of the present invention should be with scope of protection of the claims
Subject to.
Claims (7)
1. a kind of compound shown in formula A, which is characterized in that have such as flowering structure:
Wherein:
In formula A, R is aromatic rings or substituted aroma ring；
Substituent group is monosubstituted or polysubstituted halogen, nitro, trifluoromethyl, cyano, hydroxyl, methyl or methoxy.
2. compound as described in claim 1, wherein in formula A, R is phenyl ring or substituted benzene ring, thiphene ring or substituted thiophene
Ring, it is preferred that R be phenyl, 4- nitrobenzophenone, 2- fluorophenyl, 4- fluorophenyl, 2- chlorphenyl, 4- chlorphenyl, 4- bromophenyl, 2,
6- difluorophenyl, 2,6- dichlorophenyl, thienyl, 3- first thienyl, 3- chlorothiophene base, 5- chlorothiophene base.
3. compound as described in claim 1, wherein compound is any one chemical combination represented by following (1) to (7)
Object:
(1) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is hydrogen；
(2) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is 4- nitro；
(3) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is 4- fluorine；
(4) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is 4- chlorine；
(5) in formula A, R is substituted benzene ring, and the substituent group on phenyl ring is 4- bromine；
(6) in formula A, R is substituted thiophene ring, and the substituent group in thiphene ring is 3- methyl；
(7) in formula A, R is substituted thiophene ring, and the substituent group in thiphene ring is 3- chlorine.
4. a kind of preparation method of the compound as described in claim any one of 1-3, which is characterized in that use Solid-phase organic synthesis
Method preparation.
5. application of the compound in cockroach prevention and cure as described in claim any one of 1-3.
6. application of the compound in diamondback moth prevention and treatment as described in claim any one of 1-3.
7. a kind of pharmaceutical composition comprising the compound as described in claim any one of 1-3, which is characterized in that further include carrying
Body, wherein the carrier be selected from diluent, excipient, filler, adhesive, wetting agent, sorbefacient, surfactant,
One or more of lubricant, stabilizer.
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| CN108276473A (en) * | 2018-03-19 | 2018-07-13 | 中国农业大学 | A kind of insect kassinin kinin analog and its application in control of insect |
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2019
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| CN101519433A (en) * | 2009-03-20 | 2009-09-02 | 中国农业大学 | Insect allatostatin analogue modified by (substituted) phenylacrylic acid and application thereof in black beetle prevention |
| CN104447951A (en) * | 2014-11-18 | 2015-03-25 | 上海应用技术学院 | Insect allatotropin antagonist and application thereof |
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