Utilization of nicotinonitrile-2-thiol in the synthesis of new thiepino[2,3-b]pyridine derivative as an in vitro novel antitumor potent

Springer Science and Business Media LLC - Tập 22 - Trang 1674-1678 - 2012
Mohamed A. Waly1, Ibrahim I. Elhawary1, Tarek M. Elgogary1,2
1Chemistry Department, Faculty of Science (Damietta), Mansoura University, Mansoura, Egypt
2Chemistry Department, Faculty of Science (Jazan), Jazan University, Jazan, Kingdom of Saudi Arabia

Tóm tắt

A new synthesis of the thiepino[2,3-b]pyridine ring system 4 was achieved via intramolecular condensation of the 2-thiobutyrate ester nicotinonitrile derivative 6 with sodium hydride. Compound 6 was provided by alkylation of the nicotinonirile-2-thiol derivative 5 with ethyl 4-bromobutyrate in the presence of sodium carbonate. On attempting the previous alkylation in the presence of sodium hydride afforded the pyridoazepine 11 instead of thiepinopyridine 4 in one-pot synthesis. Computational quantum chemistry was utilized to explore the reaction route at the level of DFT. Data of the computational studies indicated that both anions of compounds 8 and 9 have the same stabilization energies. Antitumor activity evaluation, in vitro, of compound 4 showed high affinity as a potential novel antitumor lead.

Tài liệu tham khảo

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