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Synthesis and cytostatic activity of novel 1, 2, 3- triazolyl-tagged coumarin and iminocoumarin derivatives

Coumarin derivatives are important motifs, which can be widely found in many natural products, and many of them displaying diverse biological activities. Many molecules based on the coumarin have been synthesized utilizing innovative synthetic techniques. The diversity oriented synthesis has led to interesting derivatives including the iminocoumarins, furanocoumarins and pyranocoumarins, which have been found to be useful in photochemotherapy, antitumor and anti‐ HIV therapy, and as stimulants for central nervous system, antibacterials, anti‐inflammatory agents, anti‐coagulants, and dyes [1]. Benzofused derivatives of coumarin bridged with 1, 2, 3‐ triazole emerged as the class of compounds exhibiting the highest antiproliferative activity [2]. Furthermore, 1, 2, 3‐triazole ring has a great role as pharmacophore which is responsible for antitumor and antimicrobial activity. It is introduced in many drugs due to moderate dipole properties, rigid structure and stability in vivo. Besides, 1, 2, 3‐triazoles have attracted considerable attention in recent years because of their wide range of biological activities against various viruses, malignant cells, microorganisms and their inhibitory activities against several enzymes [3]. In order to evaluate cytostatic activity, the novel 1, 2, 3‐triazolyl‐tagged coumarin and iminocoumarin derivatives have been synthesized by click reaction of 3‐azidocoumarin or 6‐ azidoiminocoumarines with corresponding terminal acetylenes in the presence of copper as a catalyst. Of the all evaluated compounds against malignant human cell lines, 1, 2, 3‐ triazole‐ coumarin derivative with 3, 5‐ ditrifluoromethylphenyl substituent exhibited the most pronounced activity against HeLa cell lines.

coumarin ; 1, 2, 3-triazole ; iminocoumarin

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