کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1395165 | 1501202 | 2009 | 9 صفحه PDF | دانلود رایگان |
To examine the anticancer activity several novel thiazolone-based compounds containing 5-aryl-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl framework were obtained. Reaction of 5-aryl-3-phenyl-4,5-dihydropyrazole with 4-thioxo-2-thiazolidinone or 2-carbethoxymethylthio-2-thiazoline-4-one yielded starting 4- (1 and 2) or 2-substituted (11 and 12) thiazolones which were utilized in Knoevenagel condensation for obtaining a series of 5-arylidene derivatives 3–10, 13–18. Alternatively 11, 12 and their 5-arylidene derivatives were synthesized by means of 3-phenyl-5-aryl-1-thiocarbamoyl-2-pyrazoline as S,N-binucleophile via [2 + 3]-cyclocondensation approach. The structures of compounds were determined by 1H, 13C NMR, LC–MS, EI-MS and X-ray analysis. The in vitro anticancer activity of synthesized compounds were tested by the National Cancer Institute and most of them displayed anticancer activity on leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate and breast cancer cell lines. Relations between structure and activity are discussed, the most efficient anticancer compound 16 was found to be active with selective influence on colon cancer cell lines, especially on HT 29 (log GI50 = −6.37).
A number of new thiazolone-based compounds containing pyrazoline moiety 1–18 were synthesized and evaluated for their anticancer activity. The most active compound 16 (Ar = 4-OH-3,5-(OMe)2-C6H2; R = 2-OH) exhibited selective influence on colon cancer cell lines.Figure optionsDownload as PowerPoint slide
Journal: European Journal of Medicinal Chemistry - Volume 44, Issue 4, April 2009, Pages 1396–1404