A facile synthesis and microtubule-destabilizing properties of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines

European Journal of Medicinal Chemistry
Andrei I StepanovVictor V Semenov

Abstract

A series of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines (BIFAs) were prepared in good yields (60-90% for each reaction step) via a novel procedure from aminofurazanyl hydroximoyl chlorides and o-diaminobenzenes. The synthetic sequence was run under mild reaction conditions, it was robust and did not require extensive purification of intermediates or final products. Furthermore, there was no need for protection of reactive moieties allowing for the parallel synthesis of diverse BIFA derivatives. Subsequent biological evaluation of the resulting compounds revealed their anti-proliferative effects in the sea urchin embryo model and in cultured human cancer cell lines. The most active compounds showed 0.2-2 μM activities in both assay systems. The unsubstituted benzene ring of the benzoimidazole template as well as the unsubstituted amino group in the furazan ring were essential prerequisites for the antimitotic activity of BIFAs. Compound 57 bearing the 2-chlorophenyl acetamide substituent at the nitrogen atom of the imidazole ring was the most active molecule in the examined set.

References

Aug 30, 2008·Cell Cycle·Graham J Buttrick, James G Wakefield
Oct 23, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Olesya T IlkunVictor N Nemykin

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Citations

Dec 1, 2015·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Dalliane MacedoLuis Fernando Marques-Santos
Mar 10, 2020·Acta Crystallographica. Section E, Crystallographic Communications·Inna S SafyanovaValentina A Kalibabchuk
Apr 13, 2017·MedChemComm·Imran AliHaasan Y Aboul-Enein

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