Synthesis and anticancer properties of N-(5-R-benzyl-1,3-thiazol-2-yl)-2,5-dimethyl-3-furamides

Abstract

Study of the synthesis and anticancer activity of a series of N-(5-R-benzyl-1,3-thiazol-2-yl)-2,5-dimethyl-3-furamides. Methods. Organic synthesis, analytical and spectral methods, pharmacological screening. Results. N-(5-R-benzyl-1,3-thiazol-2-yl)-2,5-dimethyl-3-furamides 7a-g have been prepared in good yields by the reaction of 2-amino-5-(R-benzyl)thiazoles with 2,5-dimethyl-3-furoylchloride. Their structure was confirmed by 1 H NMR spectroscopy and microanalyses. The synthesized compounds have been evaluated for their anticancer activity against 60 cancer lines in the concentration of 10 µM. The human tumour cell lines were derived from nine different cancer types: leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. It was found that compounds 7d,e,g exhibit a high activity with GP = 29.05-35.02 % whereas 7a-c,f -moderate activity with GP = 60.31-67.36 %. The most active compound 7g showed a high inhibition activity (GI 50 <10 µM) against 54 of 58 human tumor cell lines with average GI 50 values of 4.22 µM and the colon cancer subpanel demonstrated the highest sensitivity with [a] mean GI 50 value of 2.53 µM. The most sensitive line was T-47D (BreastCancer, GI 50 = 0.088 µM). [The] MG-MID values for the most active compound 7g are less compared with those for 5-fluorouracil, curcumin and cisplatin when testing in the same manner. Conclusions. A series of new N-(5-R-benzyl-1,3-thiazol-2-yl)-2,5dimethyl-3-furamides were prepared. The compounds with high anticancer activity have been identified.

Synthesis and biological evaluation of some new 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines as antimicrobial agents

“…In view of continuation of our research work to find new effective biologically active nitrogen-containing heterocycles, [15][16][17][18][19][20][21][22][23][24][25][26][27][28] this study focuses on the synthesis and study of antimicrobial activity of new pyrazole-substituted 7H- [1,2,4]triazolo [3,4-b][1, 3,4]thiadiazines. The starting substances in the synthetic part of this study were ethyl 1-aryl-4-(bromoacetyl)-5-methyl-1H-pyrazole-3-carboxylates (3).…”