Benzo[b]furan derivatives as antiproliferative agents, with in silico predicted antitubulin activity

Design, synthesis, and biological evaluation of a new class of benzo[b]furan derivatives as antiproliferative agents, with in silico predicted antitubulin activity:

Abstract

A new series of 3-benzoylamino-5-(1H-imidazol-4-yl)methylaminobenzo[b]furans were synthesized and screened as antitumor agents. As a general trend, tested compounds showed concentration-dependent antiproliferative activity against HeLa and MCF-7 cancer cell lines, exhibiting GI₅₀ values in the low micromolar range. In most cases, insertion of a methyl substituent on the imidazole moiety improved the antiproliferative activity. Therefore, methyl-imidazolyl-benzo[b]furans compounds were tested in cell cycle perturbation experiments, producing cell cycle arrest with proapoptotic effects. Their core similarity to known colchicine binding site binders led us to further study the structure features as antitubulin agents by in silico protocols.

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A new series of 3-benzoylamino-5-(1H-imidazol-4-yl)methylaminobenzo[b]furans were synthesized and screened as antitumor agents. The MTT test (HeLa and MCF-7) underlined a significant growth inhibition effect of the derivatives 7a-f. Compounds 7b-d,f, tested in cell cycle perturbation experiments on HeLa cells produced a cell cycle arrest in G2/M phase. In addition, the structure similarity of these benzo[b]furans with known colchicine binding sites binders led us to investigate their potent interference with the microtubule system by computational analysis as a support of the observed biological effects.

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