CN103288817A - Schiff base ramification based on 1,3,4-thiadiazole and 1,3,4-oxadiazole as well as preparation method and application thereof - Google Patents
Schiff base ramification based on 1,3,4-thiadiazole and 1,3,4-oxadiazole as well as preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a Schiff base ramification based on 1,3,4-thiadiazole and 1,3,4-oxadiazole. The preparation method of the Schiff base ramification comprises the following step of: carrying out condensation reaction through 2-hydrosulfuryl-5-(2-hydroxyphenyl methylene amido)-1,3,4-thiadiazole and 1,3,4-oxadiazole ramifications in the presence of an acid-binding agent by taking acetone as a solvent and PEG-400 (Polyethylene Glycol-400) as a catalyst to prepare the Schiff base ramification based on the 1,3,4-thiadiazole and the 1,3,4-oxadiazole. The preparation method disclosed by the invention confirms the structure through an infrared spectrum, a nuclear magnetic resonance hydrogen spectrum, elemental analysis, and the like and indicates that the Schiff base ramification has the advantages of better inhibitory effect on human breast cancer cells MCF-7, human hepatoma cells SMMC-7721 and human lung cancer cells A549 and potential application prospect through the result of testing the inhibitory activity of human breast cancer cells, human hepatoma cells and human lung cancer cells.
Description
Technical field
The present invention relates to medical technical field, particularly a kind of Shiff base derivative based on 1,3,4-thiadiazoles and 1,3,4-oxadiazole and its preparation method and application.
Background technology
Multiple biological activitys such as that 1,3,4-thiadiazoles and 1,3,4-oxadiazole and derivative thereof have is anticancer, antibiotic, antimycotic, antiviral, spasmolytic are basic pharmacophoric groups, referring to: Singh H. Indian J Chem document 1), 1982,21B:480; Document 2) Yu Jianxin, Liu Fangming. SCI, 1999,8 (8): 123; Document 3) Omar AME, Aboulwafa OM. Heterocycl Chem, 1986,23:1339; Document 4) Invidiata FP, Grimaudo S, Giammanco P, et al.Farmaco, 1991,46:1489; Document 5) Holla BS, Poojary KN, Kallaraya B, et al. Farmaco, 1996,51:793; Document 6) Todoulou OG, Popadaki VA, Filippatos EC, et al. J Med Chem, 1994,29,127, particularly 1, " carbon nitrogen sulphur " structure of 3,4-thiadiazoles derivative can have better tissues cell permeability as some metal ion in the chelating organism of active centre, cause Chinese scholars thus to the extensive interest of this compounds and further investigate, become the new focus of azole compounds research.
Studies show that " SCH
2" group is the functional group that has biocompatibility and can keep molecule to rotate freely again, introduces this group in the drug molecule, is conducive to that medicine enters organism and acceptor is gone up combination in place, therefore, SCH
2Group is the important functional group that introduces usually in the medicinal design, referring to: Jian-Feng Tang document 7), Xian-Hai Lv, Xiao-Liang Wang, et al.Bioorg Med Chem, 2012,20,4226; Literary composition
Offer 8) Hu Zhiqiang, Yang Yaxun, Zhang Gongsheng, etc. organic chemistry, 2007,27 (3): 419.
In the state of the art, Song Baoan in 2005 etc., referring to: document 9) Song Baoan, Chen Caijun, Yang Song etc. chemical journal 2005,63 (18): 1720; Document 10) Chen Jiang, Xu Ruiqing, Song Baoan etc. organic chemistry .2006,26 (10): 1418, reported that with the gallic acid with antitumour activity be lead compound, a plurality of 2-substituted-phenyls-(3 have been synthesized in design, 4, the 5-trimethoxyphenyl)-1,3,4-thiadiazoles and 1,3,4-oxadiazole analog derivative is by testing this compounds to the proliferation inhibition activity of prostate cancer cell PC3 and stomach cancer cell BGC-823, the result shows: part of compounds has showed human body prostate cancer cell and stomach cancer cell breeds the inhibition ability preferably, has realized the bioactive stack of different activities group.
Zheng opened ripple etc. in 2008, referring to: document 11) Zheng Kaibo, He Jun, an outstanding person. West China pharmaceutical journal, 2008,23 (5): 528, based on amides and-1,3, the pharmacologically active of 4-thiadiazoles is primer with antitumor drug 5 FU 5 fluorouracil (5-Fu) commonly used, has synthesized serial N
1-acetylaminohydroxyphenylarsonic acid (1,3,4-thiadiazoles-2-yl)-and the 5-Fu derivative, by investigating this compounds to the proliferation inhibition activity of lung cell A549 and liver cancer cell Bel-7402, the result shows: part of compounds has showed two kinds of cancer cells breeds the inhibition ability preferably.
Hu Guoqiang in 2008 etc., referring to: document 12) Hu Guoqiang, mother chief's dawn, Wang Xin etc. Acta Pharmaceutica Sinica, 2008,43 (11): 1112, the series of loops third fluoroquinolone thiadiazoles Shiff base derivative has been synthesized in design, by measuring this compounds to the antitumour activity of human hepatoma cell SMMC-7721, human leukemia cell line HL60 and murine leukemia cell strain L1210.The result shows: majority of compounds all is 3 kinds of tumor cell lines and is just suppressing active, the IC of part of compounds
50Value reaches or is lower than the micro-molar concentration order of magnitude, for the antitumor fluoroquinolone lead compound of seeking novel texture provides new approach.
Zou Xia in 2011 is beautiful etc., referring to: document 13) Zou Xiajuan, Li Ying, Liu Zhenming etc. organic chemistry, 2011,31 (11): 1923, serial N has been synthesized in design
1-(5-substituting group-1,3,4-thiadiazoles-2-yl)-N
3-substituted-phenyl-carbamide compounds, and measured their anti-tumor activity, the result shows, part of compounds is to the growth of Lewis lung cancer mouse-borne tumor and to human leukemia cell HL-60, gastric carcinoma cells BGC-823, human liver cancer cell Bel-7402 and KB cell KB have better inhibited activity.
Based on this conception, in view of containing 1, the schiff bases compounds of 3,4-thiadiazoles has anti-tumor activity, referring to: Hu G Q document 14), Mu XK, Wang X, et al.Acta Pharm Sinica, 2008,43,1112, and link to each other by power supply daughter element S between the heterocycle, be conducive to strengthen the avidity between acceptor and the part, can produce material impact to biological activity, therefore, by the certain reaction form, synthesizing series is based on 1,3, the Shiff base derivative of 4-thiadiazoles and 1,3,4-oxadiazole, then adopt the CCK-8 method to measure this compounds to the proliferation inhibition activity of tumour cell, in the hope of realizing synergy and the bioactive stack of pharmacophoric group.
Summary of the invention
The objective of the invention is for solving cancer therapy drug of less typesly, and lack the technology of preparing problem, provide a kind of based on 1,3,4-thiadiazoles and 1,3, Shiff base derivative of 4-oxadiazole and preparation method thereof, this compounds has the good anticancer activity, is the good potential cancer therapy drug of a class.
Technical scheme of the present invention:
A kind of Shiff base derivative based on 1,3,4-thiadiazoles and 1,3,4-oxadiazole is characterized in that described derivative has the following chemical structure formula:
In the structural formula: R is the aromatic group of C1-6 alkyl, C3-8 cycloalkyl or C5-14; wherein aromatic group is by being replaced by the group of 1-3 hydroxyl, nitro, halogen atom, cyano group, C1-6 alkoxyl group or C1-6 alkyl; also can be the amino that is replaced by one or two group in C1-6 alkyl, C1-6 alkyl sulphonyl and the C1-6 alkyl-carbonyl and replace, described halogen atom is fluorine, chlorine, bromine or iodine atom.
A kind of described based on 1,3,4-thiadiazoles and 1,3, the preparation method of the Shiff base derivative of 4-oxadiazole, it is characterized in that: be solvent with acetone, PEG-400 is catalyzer, in the presence of acid binding agent, by 2-sulfydryl-5-(2-hydroxy phenyl methylene amino)-1,3,4-thiadiazoles and 1,3,4-oxadiazole analog derivative carries out the condensation reaction preparation, concrete grammar is: with 2-sulfydryl-5-(2-hydroxy phenyl methylene amino)-1,3,4 thiadiazoles, 1,3,4-oxadiazole analog derivative, the PEG-400 catalyzer, acetone solvent and acid binding agent mix and stir, back flow reaction, and the reaction times is 2-5h; After the cooling, steam solvent, separate out solid; With DMF-water recrystallization, can make target compound.
Described 1,3,4-oxadiazole analog derivative is 2-chloromethyl-5-phenyl-1,3,4-oxadiazole, 2-chloromethyl-5-fluorophenyl-1,3, the 4-oxadiazole, 2-chloromethyl-5-o-bromophenyl-1,3,4-oxadiazole, 2-chloromethyl-5-p-methoxyphenyl-1,3, the 4-oxadiazole, 2-chloromethyl-5-m-nitro base-1,3,4-oxadiazole or 2-chloromethyl-5-p-nitrophenyl-1,3, the 4-oxadiazole, 2-sulfydryl-5-(2-hydroxy phenyl methylene amino)-1,3,4 thiadiazoles and 1,3, the mol ratio of 4-oxadiazole analog derivative is 1-1.2:1, PEG-400 and 1,3, the mol ratio of 4-oxadiazole analog derivative is 1-2:4, the amount ratio of acetone solvent and 1,3,4-oxadiazole analog derivative is 1 mmole: 10-15mL.
Described acid binding agent is salt of wormwood, triethylamine, potassium hydroxide or sodium hydroxide, and acid binding agent and 2-chloromethyl-5-replaces-1, and the mol ratio of 3,4-oxadiazole is 0.6-2:1.
This preparation method's synthetic route is schematically as follows:
A kind of described based on 1,3,4-thiadiazoles and 1,3, the application of the Shiff base derivative of 4-oxadiazole, for the preparation of antitumor medicine composition, especially for the pharmaceutical composition of the anti-liver cancer of preparation, cancer of the stomach, lung cancer, mammary cancer, prostate cancer, ovarian cancer, cervical cancer, carcinoma of the pancreas, the rectum cancer, lymphatic cancer, esophagus cancer, oral carcinoma, nasopharyngeal carcinoma or skin carcinoma.
The invention has the beneficial effects as follows: the present invention is according to new drug design theory and method, prepared series first based on 1,3,4-thiadiazoles and 1,3, the Shiff base derivative of 4-oxadiazole, and proved conclusively structure by infrared spectra, proton nmr spectra and ultimate analysis etc., with the CCK-8 method, by testing this derivative to the proliferation inhibition activity of human breast cancer cell MCF-7, human hepatoma cell SMMC-7721 and human body lung cell A549, the result shows: this derivative has inhibition preferably to tumor cell proliferation, has potential application prospect.
[embodiment]
Embodiment 1:
A kind of based on 1,3,4-thiadiazoles and 1, the preparation method of the Shiff base derivative of 3,4-oxadiazole is solvent with acetone, PEG-400 is catalyzer, in the presence of acid binding agent, by 2-sulfydryl-5-(2-hydroxy phenyl methylene amino)-1,3,4-thiadiazoles and 2-chloromethyl-5-phenyl-1,3,4-oxadiazole carries out the condensation reaction preparation, and concrete grammar is:
In the 100mL round-bottomed flask, add 1.42g (6mmol) 2-sulfydryl-5-(2-hydroxy phenyl methylene amino)-1 respectively, 3,4-thiadiazoles, 1.17g (6mmol) 2-chloromethyl-5-phenyl-1,3,4-oxadiazole, 0.55g (4mmol) Anhydrous potassium carbonate, 1mmol PEG-400 and 60 mL acetone, stirring and refluxing reaction 2h; After the cooling, steam solvent, separate out solid; With DMF-water recrystallization, get light yellow solid target compound 2-(5-phenyl-1,3,4-oxadiazole-2-methylthio group)-5-(2-hydroxy phenyl methylene amino)-1,3,4-thiadiazoles 1.22g, yield 51.5%, fusing point 191.8-193.7 ℃.This product that makes is established and is numbered a.
Embodiment 2:
A kind of based on 1,3,4-thiadiazoles and 1, the preparation method of the Shiff base derivative of 3,4-oxadiazole, preparation condition method and condition are substantially the same manner as Example 1, difference is: raw materials used is 2-chloromethyl-5-fluorophenyl-1,3,4-oxadiazole, the target compound of preparation are 2-(5-fluorophenyl-1,3,4-oxadiazole-2-methylthio group)-and 5-(2-hydroxy phenyl methylene amino)-1,3, the 4-thiadiazoles.This product that makes is established and is numbered b.
Embodiment 3:
A kind of based on 1,3,4-thiadiazoles and 1, the preparation method of the Shiff base derivative of 3,4-oxadiazole, preparation condition method and condition are substantially the same manner as Example 1, difference is: raw materials used is 2-chloromethyl-5-o-bromophenyl-1,3,4-oxadiazole, the target compound of preparation are 2-(5-o-bromophenyl-1,3,4-oxadiazole-2-methylthio group)-and 5-(2-hydroxy phenyl methylene amino)-1,3, the 4-thiadiazoles.This product that makes is established and is numbered c.
Embodiment 4:
A kind of based on 1,3,4-thiadiazoles and 1, the preparation method of the Shiff base derivative of 3,4-oxadiazole, preparation condition method and condition are substantially the same manner as Example 1, difference is: raw materials used is 2-chloromethyl-5-p-methoxyphenyl-1,3,4-oxadiazole, the target compound of preparation are 2-(5-p-methoxyphenyl-1,3,4-oxadiazole-2-methylthio group)-and 5-(2-hydroxy phenyl methylene amino)-1,3, the 4-thiadiazoles.This product that makes is established and is numbered d.
Embodiment 5:
A kind of based on 1,3,4-thiadiazoles and 1, the preparation method of the Shiff base derivative of 3,4-oxadiazole, preparation condition method and condition are substantially the same manner as Example 1, difference is: raw materials used is 2-chloromethyl-5-m-nitro base-1,3,4-oxadiazole, the target compound of preparation are 2-(5-m-nitro base-1,3,4-oxadiazole-2-methylthio group)-and 5-(2-hydroxy phenyl methylene amino)-1,3, the 4-thiadiazoles.This product that makes is established and is numbered e.
Embodiment 6:
A kind of based on 1,3,4-thiadiazoles and 1,3, the preparation method of the Shiff base derivative of 4-oxadiazole, preparation condition method and condition are substantially the same manner as Example 1, and difference is: raw materials used is 2-chloromethyl-5-p-nitrophenyl-1,3, the 4-oxadiazole, the target compound of preparation is 2-(5-p-nitrophenyl-1,3,4-oxadiazole-2-methylthio group.This product that makes is established and is numbered f.
Prepared anti-tumor biological body outer screening test: sample dissolves with DMSO, and test-compound concentration is 5 * 10
-5Mol/L, chemicals treatment 48 hours adopts the CCK-8 method to measure series compound to the proliferation inhibition rate of human breast cancer cell MCF-7, human hepatoma cell SMMC-7721 and human body lung cell A549.
Detected result:
1) physical data of product is as shown in table 1:
Table 1
| Compound | Physical aspect | Recrystallization solvent | Fusing point/℃ | Yield % |
| a | Yellow powder | DMF-water | 191.8～193.7 | 51.5 |
| b | Yellow powder | DMF-water | 183.5～185.6 | 44.0 |
| c | Yellow powder | DMF-water | 210.1～212.0 | 40.2 |
| d | Yellow powder | DMF-water | 159.7～161.5 | 53.7 |
| e | Yellow powder | DMF-water | 224.6～226.5 | 41.9 |
| f | Yellow powder | DMF-water | 184.8～186.9 | 49.2 |
2) the ultimate analysis value (calculated value) of product is as shown in table 2:
Table 2
3) infrared spectra of product (IR) data are as showing: shown in 3:
Table 3
| Compound | IR(cm -1) |
| a | 3455(O-H),1620(C=N),1450(C=C),1273(C-O-C),1068(C-S) |
| b | 3454(O-H),1624(C=N),1496(C=C),1235(C-O-C),1085(C-S) |
| c | 3455(O-H),1620(C=N),1450(C=C),1273(C-O-C),1068(C-S) |
| d | 3444(O-H),1617(C=N),1502(C=C),1263(C-O-C),1084(C-S) |
| e | 3416(O-H),1618(C=N),1527 (C=C),1348(C-O-C),1152(C-S) |
| f | 3413(O-H),1618(C=N),1517 (C=C),1186(C-O-C),1087(C-S) |
4) product
1The HNMR data are as shown in table 4:
Table 4
5) proliferation inhibition rate of product is as shown in table 5:
Table 5
Detected result shows: this cancer therapy drug has inhibition preferably to tumor cell proliferation, has potential application prospect.
Foregoing, it only is representative embodiment of the present invention, be not that the present invention is done any type of restriction, every foundation technical spirit of the present invention all still belongs in the scope of technical solution of the present invention any simple modification, equivalent variations and modification that above embodiment does.
Claims (5)
1. Shiff base derivative based on 1,3,4-thiadiazoles and 1,3,4-oxadiazole, it is characterized in that: described derivative has the following chemical structure formula:
In the structural formula: R is the aromatic group of C1-6 alkyl, C3-8 cycloalkyl or C5-14; wherein aromatic group is by being replaced by the group of 1-3 hydroxyl, nitro, halogen atom, cyano group, C1-6 alkoxyl group or C1-6 alkyl; also can be the amino that is replaced by one or two group in C1-6 alkyl, C1-6 alkyl sulphonyl and the C1-6 alkyl-carbonyl and replace, described halogen atom is fluorine, chlorine, bromine or iodine atom.
2. one kind according to claim 1 based on 1,3,4-thiadiazoles and 1,3, the preparation method of the Shiff base derivative of 4-oxadiazole, it is characterized in that: be solvent with acetone, PEG-400 is catalyzer, in the presence of acid binding agent, by 2-sulfydryl-5-(2-hydroxy phenyl methylene amino)-1,3,4-thiadiazoles and 1,3,4-oxadiazole analog derivative carries out the condensation reaction preparation, concrete grammar is: with 2-sulfydryl-5-(2-hydroxy phenyl methylene amino)-1,3,4 thiadiazoles, 1,3,4-oxadiazole analog derivative, the PEG-400 catalyzer, acetone solvent and acid binding agent mix and stir, back flow reaction, and the reaction times is 2-5h; After the cooling, steam solvent, separate out solid; With DMF-water recrystallization, can make target compound.
3. described based on 1,3,4-thiadiazoles and 1 according to claim 2, the preparation method of the Shiff base derivative of 3,4-oxadiazole is characterized in that: described 1,3,4-oxadiazole analog derivative is 2-chloromethyl-5-phenyl-1,3, the 4-oxadiazole, 2-chloromethyl-5-fluorophenyl-1,3,4-oxadiazole, 2-chloromethyl-5-o-bromophenyl-1,3, the 4-oxadiazole, 2-chloromethyl-5-p-methoxyphenyl-1,3,4-oxadiazole, 2-chloromethyl-5-m-nitro base-1,3,4-oxadiazole or 2-chloromethyl-5-p-nitrophenyl-1,3,4-oxadiazole, 2-sulfydryl-5-(2-hydroxy phenyl methylene amino)-1,3, the mol ratio of 4 thiadiazoles and 1,3,4-oxadiazole analog derivative is 1-1.2:1, PEG-400 and 1, the mol ratio of 3,4-oxadiazole analog derivative is 1-2:4, acetone solvent and 1, the amount ratio of 3,4-oxadiazole analog derivative is 1 mmole: 10-15mL.
4. described based on 1 according to claim 2,3,4-thiadiazoles and 1,3, the preparation method of the Shiff base derivative of 4-oxadiazole is characterized in that: described acid binding agent is salt of wormwood, triethylamine, potassium hydroxide or sodium hydroxide, and acid binding agent and 2-chloromethyl-5-replaces-1, the mol ratio of 3,4-oxadiazole is 0.6-2:1.
5. one kind according to claim 1 based on 1,3,4-thiadiazoles and 1,3, the application of the Shiff base derivative of 4-oxadiazole, it is characterized in that: for the preparation of antitumor medicine composition, especially for the pharmaceutical composition of the anti-liver cancer of preparation, cancer of the stomach, lung cancer, mammary cancer, prostate cancer, ovarian cancer, cervical cancer, carcinoma of the pancreas, the rectum cancer, lymphatic cancer, esophagus cancer, oral carcinoma, nasopharyngeal carcinoma or skin carcinoma.
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Cited By (1)
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| CN109180621A (en) * | 2018-08-01 | 2019-01-11 | 河南省锐达医药科技有限公司 | The preparation and the application in terms for the treatment of of cancer of a kind of New Schiff Base class compound |
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Application publication date: 20130911 |