Hanan Salah, Nadia A.A. Elkanzi, Azhaar T. Alsaggaf, Alaa Y. Moustafa, Faeza Alkorbi, Ali M. Ali
{"title":"通过微波和传统方法下的一锅三组分反应设计噻唑烷酮类化合物并提高其细胞毒活性","authors":"Hanan Salah, Nadia A.A. Elkanzi, Azhaar T. Alsaggaf, Alaa Y. Moustafa, Faeza Alkorbi, Ali M. Ali","doi":"10.4314/bcse.v38i2.15","DOIUrl":null,"url":null,"abstract":"Treatment of sulfamethoxazole (SMZ ) (1) with different aromatic aldehydes 2a-f within few minutes (5-8 min) afforded the corresponding Schiff bases 3a-f which were subjected to react with thioglycolic acid (4) under refluxing toluene/dimethlformamide (DMF) in (1:1) ratio for 12-17 h, yielded N-(5-methylisoxazol-3-yl)-4-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)benzenesulfon- amide derivatives 5a-f. On the other hand, the same products 5a-f were obtained when SMZ (1) was treated with a mixture of the same aromatic aldehydes 2a-f and thioglycolic acid 4 via one-pot, three-component reaction under microwave irradiation. The key advantages of this process were high yields 79-88%, shorter reaction times 6-11 min., easy work-up, and problems associated with toxic solvent use (cost, safety, pollution) were avoided. The structures of newly compounds were elucidated by elemental and spectral analyses. Three compounds 5a, 5b and 5f were tested for cytotoxicity against four human cancer cell lines MCF-7, HePG2, HCT 116 and 116 PC-3. Compound 5b exhibited the most potent cytotoxic properties on HePG2 and PC-3. Furthermore, it showed inhabitory effect against MCF-7 and HCT 116 cells. \nKEY WORDS: Sulfamethoxazole, 4-Thiazolidinones, Schiff bases, Multicomponent reaction, Microwave, Traditional methods and cytotoxicity \nBull. Chem. Soc. Ethiop. 2024, 38(2), 481-491. \nDOI: https://dx.doi.org/10.4314/bcse.v38i2.15","PeriodicalId":9501,"journal":{"name":"Bulletin of the Chemical Society of Ethiopia","volume":null,"pages":null},"PeriodicalIF":1.3000,"publicationDate":"2024-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Design and cytotoxic activity of thiazolidinones via one-pot, three component reaction under microwave and traditional method\",\"authors\":\"Hanan Salah, Nadia A.A. Elkanzi, Azhaar T. Alsaggaf, Alaa Y. Moustafa, Faeza Alkorbi, Ali M. Ali\",\"doi\":\"10.4314/bcse.v38i2.15\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Treatment of sulfamethoxazole (SMZ ) (1) with different aromatic aldehydes 2a-f within few minutes (5-8 min) afforded the corresponding Schiff bases 3a-f which were subjected to react with thioglycolic acid (4) under refluxing toluene/dimethlformamide (DMF) in (1:1) ratio for 12-17 h, yielded N-(5-methylisoxazol-3-yl)-4-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)benzenesulfon- amide derivatives 5a-f. On the other hand, the same products 5a-f were obtained when SMZ (1) was treated with a mixture of the same aromatic aldehydes 2a-f and thioglycolic acid 4 via one-pot, three-component reaction under microwave irradiation. The key advantages of this process were high yields 79-88%, shorter reaction times 6-11 min., easy work-up, and problems associated with toxic solvent use (cost, safety, pollution) were avoided. The structures of newly compounds were elucidated by elemental and spectral analyses. Three compounds 5a, 5b and 5f were tested for cytotoxicity against four human cancer cell lines MCF-7, HePG2, HCT 116 and 116 PC-3. Compound 5b exhibited the most potent cytotoxic properties on HePG2 and PC-3. Furthermore, it showed inhabitory effect against MCF-7 and HCT 116 cells. \\nKEY WORDS: Sulfamethoxazole, 4-Thiazolidinones, Schiff bases, Multicomponent reaction, Microwave, Traditional methods and cytotoxicity \\nBull. Chem. Soc. Ethiop. 2024, 38(2), 481-491. \\nDOI: https://dx.doi.org/10.4314/bcse.v38i2.15\",\"PeriodicalId\":9501,\"journal\":{\"name\":\"Bulletin of the Chemical Society of Ethiopia\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.3000,\"publicationDate\":\"2024-01-23\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bulletin of the Chemical Society of Ethiopia\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.4314/bcse.v38i2.15\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bulletin of the Chemical Society of Ethiopia","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.4314/bcse.v38i2.15","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Design and cytotoxic activity of thiazolidinones via one-pot, three component reaction under microwave and traditional method
Treatment of sulfamethoxazole (SMZ ) (1) with different aromatic aldehydes 2a-f within few minutes (5-8 min) afforded the corresponding Schiff bases 3a-f which were subjected to react with thioglycolic acid (4) under refluxing toluene/dimethlformamide (DMF) in (1:1) ratio for 12-17 h, yielded N-(5-methylisoxazol-3-yl)-4-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)benzenesulfon- amide derivatives 5a-f. On the other hand, the same products 5a-f were obtained when SMZ (1) was treated with a mixture of the same aromatic aldehydes 2a-f and thioglycolic acid 4 via one-pot, three-component reaction under microwave irradiation. The key advantages of this process were high yields 79-88%, shorter reaction times 6-11 min., easy work-up, and problems associated with toxic solvent use (cost, safety, pollution) were avoided. The structures of newly compounds were elucidated by elemental and spectral analyses. Three compounds 5a, 5b and 5f were tested for cytotoxicity against four human cancer cell lines MCF-7, HePG2, HCT 116 and 116 PC-3. Compound 5b exhibited the most potent cytotoxic properties on HePG2 and PC-3. Furthermore, it showed inhabitory effect against MCF-7 and HCT 116 cells.
KEY WORDS: Sulfamethoxazole, 4-Thiazolidinones, Schiff bases, Multicomponent reaction, Microwave, Traditional methods and cytotoxicity
Bull. Chem. Soc. Ethiop. 2024, 38(2), 481-491.
DOI: https://dx.doi.org/10.4314/bcse.v38i2.15
期刊介绍:
The Bulletin of the Chemical Society of Ethiopia (BCSE) is a triannual publication of the Chemical Society of Ethiopia. The BCSE is an open access and peer reviewed journal. The BCSE invites contributions in any field of basic and applied chemistry.