CN104130307A - 闭花木酮Cleistanone的O-(四氢吡咯基)乙基衍生物、制备方法及其用途 - Google Patents
闭花木酮Cleistanone的O-(四氢吡咯基)乙基衍生物、制备方法及其用途 Download PDFInfo
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- CN104130307A CN104130307A CN201410375051.2A CN201410375051A CN104130307A CN 104130307 A CN104130307 A CN 104130307A CN 201410375051 A CN201410375051 A CN 201410375051A CN 104130307 A CN104130307 A CN 104130307A
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- Prior art keywords
- flowers
- ketone cleistanone
- trees ketone
- pyrrolidine base
- ethyl derivative
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- XURLTFUKDPZAPN-QFIPXVFZSA-N Cleistanone Natural products O(C)[C@H]1OC(=O)c2c(-c3cc4OCOc4cc3)c3c(c(O)c12)cc(OC)c(OC)c3 XURLTFUKDPZAPN-QFIPXVFZSA-N 0.000 title claims abstract description 66
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 230000000840 anti-viral effect Effects 0.000 claims abstract description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 94
- GEIFQLXIDUDMNZ-PCJVTFPHSA-N (4aR,4bR,6aR,8S,10aR,10bR,12R,12aR)-12-hydroxy-1,1,1',1',4a,10a,10b-heptamethyl-3'-methylidenespiro[3,4,4b,5,6,6a,7,9,10,11,12,12a-dodecahydrochrysene-8,2'-cyclopentane]-2-one Chemical compound CC1(C)CCC(=C)[C@@]11C[C@@H](CC[C@H]2[C@]3(C[C@@H](O)[C@H]4C(C)(C)C(=O)CC[C@@]42C)C)[C@@]3(C)CC1 GEIFQLXIDUDMNZ-PCJVTFPHSA-N 0.000 claims description 62
- 150000002576 ketones Chemical class 0.000 claims description 60
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 241000700605 Viruses Species 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 241000725643 Respiratory syncytial virus Species 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 235000002639 sodium chloride Nutrition 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000010828 elution Methods 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 239000012071 phase Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 5
- 241000712431 Influenza A virus Species 0.000 claims description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 235000007715 potassium iodide Nutrition 0.000 claims description 3
- 229960004839 potassium iodide Drugs 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 241001529453 unidentified herpesvirus Species 0.000 claims description 3
- 241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000003443 antiviral agent Substances 0.000 abstract 2
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 16
- 238000010790 dilution Methods 0.000 description 12
- 239000012895 dilution Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 238000010186 staining Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 229940079593 drug Drugs 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 210000002966 serum Anatomy 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 231100000645 Reed–Muench method Toxicity 0.000 description 6
- 230000001464 adherent effect Effects 0.000 description 6
- 230000001413 cellular effect Effects 0.000 description 6
- 231100000433 cytotoxic Toxicity 0.000 description 6
- 230000001472 cytotoxic effect Effects 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000003203 everyday effect Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000004083 survival effect Effects 0.000 description 6
- 239000003053 toxin Substances 0.000 description 5
- 231100000765 toxin Toxicity 0.000 description 5
- 230000003612 virological effect Effects 0.000 description 5
- 201000010099 disease Diseases 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
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- 241000700584 Simplexvirus Species 0.000 description 3
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- 208000015181 infectious disease Diseases 0.000 description 3
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- 238000011160 research Methods 0.000 description 3
- 210000002345 respiratory system Anatomy 0.000 description 3
- 238000013207 serial dilution Methods 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XBZYWSMVVKYHQN-MYPRUECHSA-N (4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-9-[(sulfooxy)methyl]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Chemical compound C1C[C@H](O)[C@@](C)(COS(O)(=O)=O)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C XBZYWSMVVKYHQN-MYPRUECHSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000785597 Cleistanthus Species 0.000 description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- 208000002352 blister Diseases 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000012470 diluted sample Substances 0.000 description 2
- 206010014599 encephalitis Diseases 0.000 description 2
- 208000037797 influenza A Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000197194 Bulla Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 208000029433 Herpesviridae infectious disease Diseases 0.000 description 1
- 241001500351 Influenzavirus A Species 0.000 description 1
- 206010056254 Intrauterine infection Diseases 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010046306 Upper respiratory tract infection Diseases 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
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CN201410375051.2A CN104130307B (zh) | 2014-07-31 | 2014-07-31 | 闭花木酮Cleistanone的O-(四氢吡咯基)乙基衍生物、制备方法及其用途 |
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CN201410375051.2A CN104130307B (zh) | 2014-07-31 | 2014-07-31 | 闭花木酮Cleistanone的O-(四氢吡咯基)乙基衍生物、制备方法及其用途 |
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CN104130307A true CN104130307A (zh) | 2014-11-05 |
CN104130307B CN104130307B (zh) | 2015-12-02 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104523705A (zh) * | 2014-12-10 | 2015-04-22 | 南京大学 | 闭花木酮的o-(咪唑基)乙基衍生物在制备抗病毒药物中的应用 |
CN104672295A (zh) * | 2015-03-10 | 2015-06-03 | 南京大学 | 闭花木酮的o-(***基)乙基衍生物及其制备方法和应用 |
CN104800212A (zh) * | 2015-05-12 | 2015-07-29 | 南京大学 | Daphmalenine A衍生物在制备抗病毒药物中的应用 |
CN104825465A (zh) * | 2015-04-15 | 2015-08-12 | 南京广康协生物医药技术有限公司 | 闭花木酮的o-(1h-四氮唑基)乙基衍生物在制备抗病毒药物中的应用 |
-
2014
- 2014-07-31 CN CN201410375051.2A patent/CN104130307B/zh not_active Expired - Fee Related
Non-Patent Citations (3)
Title |
---|
CHIMMANI RAMESH ET AL.: "Arylnaphthalide Lignans from Cleistanthus collinus", 《CHEM.PHARM.BULL.》, vol. 51, no. 11, 30 November 2003 (2003-11-30), pages 1299 - 1300 * |
VAN TRINH THI THANH ET AL.: "Cleistanone: A Triterpenoid from Cleistanthus indochinensis with a new carbon skeleton", 《EUROPEAN JOURNAL OF ORGANIC CHEMISTRY》, vol. 2011, no. 22, 7 June 2011 (2011-06-07), pages 4108 - 4111 * |
王洋: "丘生闭花木中的芳基N-酰基萘胺木脂素类", 《国外医学.中医中药分册》, vol. 27, no. 1, 30 January 2005 (2005-01-30), pages 58 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104523705A (zh) * | 2014-12-10 | 2015-04-22 | 南京大学 | 闭花木酮的o-(咪唑基)乙基衍生物在制备抗病毒药物中的应用 |
CN104672295A (zh) * | 2015-03-10 | 2015-06-03 | 南京大学 | 闭花木酮的o-(***基)乙基衍生物及其制备方法和应用 |
CN104825465A (zh) * | 2015-04-15 | 2015-08-12 | 南京广康协生物医药技术有限公司 | 闭花木酮的o-(1h-四氮唑基)乙基衍生物在制备抗病毒药物中的应用 |
CN104800212A (zh) * | 2015-05-12 | 2015-07-29 | 南京大学 | Daphmalenine A衍生物在制备抗病毒药物中的应用 |
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Inventor after: Chao Shujun Inventor after: Yu Jie Inventor after: Wang Cuihong Inventor after: Liu Lixia Inventor before: Huang Rong Inventor before: Wu Junyi Inventor before: Wu Junhua |
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