CN104402762B - The synthesis of with anticancer activity 3,5-dichloro-salicylaldehyde's contracting AMPD schiff bases and application - Google Patents
The synthesis of with anticancer activity 3,5-dichloro-salicylaldehyde's contracting AMPD schiff bases and application Download PDFInfo
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- CN104402762B CN104402762B CN201410830039.6A CN201410830039A CN104402762B CN 104402762 B CN104402762 B CN 104402762B CN 201410830039 A CN201410830039 A CN 201410830039A CN 104402762 B CN104402762 B CN 104402762B
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- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 239000002262 Schiff base Substances 0.000 title claims abstract description 37
- -1 AMPD schiff bases Chemical class 0.000 title claims abstract description 32
- 230000001093 anti-cancer Effects 0.000 title claims abstract description 10
- 101150035093 AMPD gene Proteins 0.000 title claims description 8
- 230000015572 biosynthetic process Effects 0.000 title description 6
- 238000003786 synthesis reaction Methods 0.000 title description 6
- 239000013078 crystal Substances 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229960000935 dehydrated alcohol Drugs 0.000 claims abstract description 7
- 238000013461 design Methods 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 238000010189 synthetic method Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 8
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 7
- 239000003005 anticarcinogenic agent Substances 0.000 claims 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 5
- 150000004753 Schiff bases Chemical class 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000000470 constituent Substances 0.000 abstract description 2
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 238000011275 oncology therapy Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N Trimethylene glycol Natural products OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 3
- WSUWZPYQCSWACI-UHFFFAOYSA-N 3,4-dichloro-2-hydroxybenzaldehyde Chemical class OC1=C(Cl)C(Cl)=CC=C1C=O WSUWZPYQCSWACI-UHFFFAOYSA-N 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 210000004881 tumor cell Anatomy 0.000 description 6
- 239000012531 culture fluid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 206010005003 Bladder cancer Diseases 0.000 description 2
- 206010008342 Cervix carcinoma Diseases 0.000 description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- 201000010881 cervical cancer Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 201000005112 urinary bladder cancer Diseases 0.000 description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000013553 cell monolayer Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 210000005260 human cell Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of 3,5 dichloro-salicylaldehydes with anticancer activity to contract the synthetic method of 2 amino 2 methyl 1,3 propylene glycol schiff bases and application.The contract molecular formula of 2 amino 2 methyl 1,3 propylene glycol schiff bases of 3,5 dichloro-salicylaldehydes is: C11H13Cl2NO3, molecular weight is: 278.13, has active anticancer.(1) by analytically pure for 1.910g 3,5 dichloro-salicylaldehydes are placed in there-necked flask, the dehydrated alcohol heated and stirred adding 15ml treats that it is completely dissolved, it is subsequently adding analytically pure 2 amino 2 methyl 1 of 1.051g, 3 propylene glycol, add the dehydrated alcohol of 10ml, heating in water bath, design temperature is 65 DEG C, return stirring about 120 minutes.(2) cooling at room temperature, naturally volatilization crystallization, after standing 3 days, obtain yellow bulk crystals.3,5 dichloro-salicylaldehydes, the 2 amino 2 methyl 1,3 propylene glycol schiff bases that contract are applied to prepare cancer therapy drug.The present invention has that technique is simple, with low cost, chemical constituent is easily controllable, reproducible and yield advantages of higher.
Description
Technical field
The present invention relates to a kind of tool active anticancer 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol Schiff
The synthesis of alkali and application.
Background technology
Recent study finds that schiff base compounds has the biological activitys such as good antibacterial, antiinflammatory, antitumor, Schiff
The synthesis of alkali and bioactive research have become pharmaceutical chemistry, the important topic of biologist's research, for social development and skill
Art progress plays the effect become more and more important.Particularly efficiently in short supply present of new drug, the medicine of exploitation tool high anti-cancer activity
It is to solve one of efficient new drug problem in short supply method.3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases
There is the biological activity of uniqueness, can serve as design synthesis and there is the medicine such as the most antibacterial, the antitumor of low toxicity of application prospect,
There is potential use.
Summary of the invention
The purpose of the present invention synthesizes compound 3,5-dichloro-salicylaldehyde contracting 2-amino-2-with anticancer activity for design exactly
Methyl isophthalic acid, ammediol schiff bases and be applied to cook cancer therapy drug, utilize the method synthesis 3 that heating in water bath refluxes, 5-bis-chlorine water
Poplar al 2-amino-2-methyl-1,3-propylene glycol schiff bases.
The molecular formula of the 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases that the present invention relates to is:
C11H13Cl2NO3, molecular weight is: 278.13, and crystal structural data is shown in Table 1, and bond distance's bond angle data are shown in Table 2.
The crystallographic parameter of table one: 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases
The bond distance of table two: 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff basesWith bond angle (°)
The synthetic method concrete steps of described 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases
For:
(1) by analytically pure for 1.910g 3,5-dichloro-salicylaldehyde is placed in there-necked flask, and the dehydrated alcohol adding 15ml adds
Thermal agitation treats that it is completely dissolved, and is subsequently adding the analytically pure AMPD of 1.051g, adds 10ml
Dehydrated alcohol, heating in water bath, design temperature is 65 DEG C, return stirring about 120 minutes.
(2) cooled down at room temperature by the solution that step (1) obtains, naturally volatilizing crystallizes, and after standing 3 days, obtains yellow
Bulk crystals i.e. compound 3,5-dichloro-salicylaldehyde contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases.Pass through single crystal diffractometer
Measure the structure of 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases.
The present invention has that technique is simple, with low cost, chemical constituent is easily controllable, reproducible and yield advantages of higher.
Accompanying drawing explanation
Fig. 1 is the enforcement figure of 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases of the present invention.
Fig. 2 is the structure chart of 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases of the present invention.
Fig. 3 is the three dimensional structure heap of 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases of the present invention
Long-pending figure.
Detailed description of the invention
Embodiment:
The molecular formula of the 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases that the present invention relates to is:
C11H13Cl2NO3, molecular weight is: 278.13, and crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
The synthetic method of 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases concretely comprises the following steps:
(1) by analytically pure for 1.910g 3,5-dichloro-salicylaldehyde is placed in there-necked flask, and the dehydrated alcohol adding 15ml adds
Thermal agitation treats that it is completely dissolved, and is subsequently adding the analytically pure AMPD of 1.051g, adds 10ml
Dehydrated alcohol, heating in water bath, design temperature is 65 DEG C, return stirring about 120 minutes.
(2) solution that step (1) obtains is volatilized the most naturally crystallization, after standing 3 days, obtain the block brilliant of yellow
Body i.e. compound 3,5-dichloro-salicylaldehyde contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases.3 are measured by single crystal diffractometer,
The structure of 5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases.
Multiple people is swollen by 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases with anticancer activity
The proliferation inhibition activity experiment of tumor cell strain:
(1) cell strain is cultivated with cell:
Human hepatoma cell strain (BEL-7404), human liver cancer cell (HepG2), cervical cancer cell are selected in this experiment
(HeLa), human bladder cancer cell (T-24), 5 kinds of human cell lines such as normal liver cell's strain (HL-7702).All cells strain is all trained
Support containing 10wt% calf serum, 100U/mL penicillin, 100U/mL streptomycin RPMI-1640 culture fluid in, put 37 DEG C and contain
Volumetric concentration 5%CO2Incubator is cultivated.
(2) preparation of testing compound:
Used 3, purity >=95% of 5-dichloro-salicylaldehyde's contracting AMPD schiff bases, by it
The whole solution of 20 μm ol/L it is configured to after the dilution of DMSO liquid storage physiological buffer, wherein final concentration≤1% of cosolvent DMSO,
Test the compound suppression degree to various growth of tumour cell under this concentration.
(3) cell growth inhibition test (mtt assay):
1) take the logarithm the tumor cell of trophophase, after trypsinization, join with the culture fluid containing 10% calf serum
Make the cell suspension that concentration is 5000/ml, be inoculated in 96 well culture plates with every hole 190 μ l, make cell density to be measured extremely
1000～10000 holes (edge hole is filled with aseptic PBS)；
2) 5%CO2, to hatch 24 hours, be paved with at the bottom of hole to cell monolayer for 37 DEG C, every hole adds the medicine of finite concentration gradient
10 μ L, each Concentraton gradient sets 4 multiple holes；
3) 5%CO2, hatch 48 hours for 37 DEG C, observe under inverted microscope；
4) every hole adds the MTT solution (5mg/mL PBS, i.e. 0.5%MTT) of 10 μ L, continues to cultivate 4 hours；
5) terminating cultivating, carefully suck culture fluid in hole, every hole adds the DMSO of 150 μ L and fully dissolves first a ceremonial jade-ladle, used in libation precipitation, shakes
After swinging device mixing, being 570nm at microplate reader wavelength, reference wavelength is the optical density value that 450nm measures each hole；
6) simultaneously arrange zeroing hole (culture medium, MTT, DMSO), control wells (cell, the medicine dissolution medium of same concentrations,
Culture fluid, MTT, DMSO).
7) according to the optical density value (OD value) recorded, judging living cells quantity, OD value is the biggest, and cytoactive is the strongest.Profit
With formula:
Calculate the suppression ratio of drug on tumor cell growth, then calculate each test-compound respectively to multiple with Bliss method
Human tumor cell line and the IC of Human normal hepatocyte strain50Value.
3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases is to human hepatoma cell strain (BEL-
7404), human liver cancer cell (HepG2), cervical cancer cell (HeLa), human bladder cancer cell (T-24), normal liver cell's strain
Etc. (HL-7702) suppression ratio of growth of tumour cell is shown in Table three, to multiple human tumor cell line and the IC of Human normal hepatocyte strain50
Value is shown in Table four.
The suppression to different cell strains of table three: the 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases
Rate
| BEL-7404 | HepG2 | HeLa | T-24 | HL-7702 |
| 37.41±1.53 | 10.39±0.96 | 37.84±1.53 | 43.81±2.39 | 38.03±1.67 |
Table four: the 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases half to different cell strains
Inhibition concentration (IC50, μM)
| BEL-7404 | HepG2 | HeLa | T-24 | HL-7702 |
| 51.37±0.96 | 349.81±3.99 | 92.37±1.69 | 29.11±0.93 | 80.16±2.21 |
Claims (2)
1. compound 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases with anticancer activity, its
It is characterised by that 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases molecular formula is: C11H13Cl2NO3, point
Son amount is: 278.13, and compound 3,5-dichloro-salicylaldehyde's contracting AMPD schiff bases has anticancer work
Property, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two；
The synthetic method of described 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases concretely comprises the following steps:
(1) by analytically pure for 1.910g 3,5-dichloro-salicylaldehyde is placed in there-necked flask, and the dehydrated alcohol heating adding 15ml is stirred
Mix and treat that it is completely dissolved, be subsequently adding the analytically pure AMPD of 1.051g, add the nothing of 10ml
Water-ethanol, heating in water bath, design temperature is 65 DEG C, return stirring 120 minutes；
(2) cooled down at room temperature by the solution that step (1) obtains, naturally volatilizing crystallizes, and after standing 3 days, obtains the bulk of yellow
Crystal i.e. compound 3,5-dichloro-salicylaldehyde contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases；Measured by single crystal diffractometer
The structure of 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases；
The crystallographic parameter of table one: 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases
The bond distance of table two: 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff basesWith bond angle (°)
Answering of 3,5-dichloro-salicylaldehyde's contracting 2-amino-2-methyl-1,3-propylene glycol schiff bases the most according to claim 1
With, it is characterised in that 3,5-dichloro-salicylaldehyde's contracting AMPD schiff bases are applied to prepare anticarcinogen
Thing.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880869A (en) * | 2014-04-05 | 2014-06-25 | 桂林理工大学 | Anti-cancer drug [Cu2(L<4>)(L<6>)] and in-situ synthesis method thereof |
| CN103922992A (en) * | 2014-04-25 | 2014-07-16 | 温州大学 | Anti-cancer active indolone derivate as well as synthesis method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS6022337B2 (en) * | 1976-08-19 | 1985-06-01 | オリエンタル写真工業株式会社 | Heat-developable photosensitive material |
| WO2008075866A1 (en) * | 2006-12-18 | 2008-06-26 | Yong Jin Park | A composition comprising the processed extract of panax quinquefolium l. for the prevention and treatment of cancer |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103880869A (en) * | 2014-04-05 | 2014-06-25 | 桂林理工大学 | Anti-cancer drug [Cu2(L<4>)(L<6>)] and in-situ synthesis method thereof |
| CN103922992A (en) * | 2014-04-25 | 2014-07-16 | 温州大学 | Anti-cancer active indolone derivate as well as synthesis method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| Mixed-ligand Cu(II)evanillin Schiff base complexes;effect of coligands on their DNA binding,DNA cleavage,SOD mimetic and anticancer activity;Sartaj Tabassum等;《European Journal of Medicinal Chemistry》;20120823;第60卷;第216-232页 * |
| Schiff Bases of Salicylaldehyde and Their Cobalt(II) Derivatives as Antitumor Agents;Hodnett Ernest M.，Willie Winfred;《Proceedings of the Oklahoma Academy of Science》;19651231;第110页表II * |
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Application publication date: 20150311 Assignee: Yancheng Aipinyue Network Technology Co.,Ltd. Assignor: Li Zaigao Contract record no.: X2023980047070 Denomination of invention: Synthesis and application of 3,5-dichlorosalicylialdehyde 2-amino-2-methyl-1,3-propanediol Schiff base with anticancer activity Granted publication date: 20160928 License type: Common License Record date: 20231120 |
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