ChemInform Abstract: Substituted 2,5′‐Bi‐1H‐benzimidazoles: Topoisomerase I Inhibition and Cytotoxicity.

Abstract

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Synthesis and Biological Evaluation of Novel Bisbenzimidazoles as Escherichia coli Topoisomerase IA Inhibitors and Potential Antibacterial Agents

“…All the deacetylated intermediates were then reduced by catalytic hydrogenation using 10% Pd/C at ambient temperature to provide diamine derevatives 5a – k in good yield (Scheme ). 2-Aryl-5-cyano-1 H -benzimidazole 8a – c were synthesized in 75–90% yield by reacting 4-cyano-1,2-phenylenediamine 6 with the appropriate substituted benzaldehydes 7a – c using reported procedures (Scheme ). , Catalytic reduction of 8a – c using Ni–Al alloy in the presence of 75% formic acid in water provided intermediates 9a – c in good yield (Scheme ). , All final compounds were then converted to respective hydrochloride salts to make them water-soluble by passing the dried HCl gas in the methanolic solution of respective bisbenzimidazoles.…”

“…30,31 Catalytic reduction of 8a−c using Ni−Al alloy in the presence of 75% formic acid in water provided intermediates 9a−c in good yield (Scheme 2). 32,33 All final compounds were then converted to respective hydrochloride salts to make them water-soluble by passing the dried HCl gas in the methanolic solution of respective bisbenzimidazoles. The synthetic analogues of bisbenzimidazoles 11a−i and 12a−e have shown good antibacterial potential in comparison to 10a−j, suggesting that substitution at phenyl ring plays an important role in antibacterial activity of bisbenzimidazoles.…”

“…1 H NMR (400 MHz, DMSO-d 6 + D 2 O) δ ppm 1.34 (t, J = 7.32 Hz, 3H), 4.12 (q, J = 7. 32 5-Cyano-2-(3,4-dimethoxyphenyl)benzimidazole (8c). This compound was synthesized by reported procedure.…”

Copper(I) Chloride Mediated Amination of Halobenzenes via Azides: Scope, Mechanistic Aspects, and C–C Cleavage Reactions

“…1 H NMR (300 MHz, DMSO): δ 6.81−6.76 (m, 2H), 6.55 (d, J = 8.0 Hz, 2H), 5.44 (s, 2H), 4.84 (s, 2H). Note: The NMR data of 4m has been reported in CDCl 3 54 and DMSO-d 6 , 55 with both reported chemical shifts being near-identical. We have compared our data to that of a commercial sample (Supporting Information, page S63), measured in both CDCl 3 and DMSO-d 6 , and note that the data in ref 55 does not match the reported DMSO-d 6 but CDCl 3 .…”

“…3,4-Diaminobenzonitrile (4m). 54,55 Yield: 24%. 1 H NMR (300 MHz, DMSO): δ 6.81−6.76 (m, 2H), 6.55 (d, J = 8.0 Hz, 2H), 5.44 (s, 2H), 4.84 (s, 2H).…”