Biopolym. Cell. 2020; 36(1):74-83.
Bioorganic Chemistry
Synthesis and anticancer properties of N-(5-R-benzyl-1,3-thiazol-2-yl)-2,5-dimethyl-3-furamides
1Matiichuk Y. E., 2Ostapiuk Y. V., 1Chaban T. I., 1Ogurtsov V. V., 2Matiychuk V. S.
  1. Danylo Halytsky Lviv National Medical University
    69, Pekarska Str., Lviv, Ukraine, 79010
  2. Ivan Franko National University of Lviv
    4, Hrushevskoho Str., Lviv, Ukraine, 79005

Abstract

Aim. 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 1H 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 (GI50<10 µM) against 54 of 58 human tumor cell lines with average GI50 values of 4.22 µM and the colon cancer subpanel demonstrated the highest sensitivity with [a] mean GI50 value of 2.53 µM. The most sensitive line was T-47D (BreastCancer, GI50 = 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)-2,5-dimethyl-3-furamides were prepared. The compounds with high anticancer activity have been identified.
Keywords: synthesis, arylation, acylation, 2-amino-5-arylmetylthiazole, anticancer activity.

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