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N,2,6-Trisubstituted 1H-benzimidazole derivatives as a new scaffold of antimicrobial and anticancer agents: design, synthesis, in vitro evaluation, and in silico studies

RSC advances, 2023, Vol.13 (1), p.399-420 [Peer Reviewed Journal]

Copyright Royal Society of Chemistry 2023 ;This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry ;ISSN: 2046-2069 ;EISSN: 2046-2069 ;DOI: 10.1039/d2ra06667j

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  • Title:
    N,2,6-Trisubstituted 1H-benzimidazole derivatives as a new scaffold of antimicrobial and anticancer agents: design, synthesis, in vitro evaluation, and in silico studies
  • Author: Em Canh Pham ; Tuong Vi Le Thi ; Huong Ha Ly Hong ; Bich Ngoc Vo Thi ; Vong, Long B ; Thao Thanh Vu ; Vo, Duy Duc ; Ngoc Vi Tran Nguyen ; Khanh Nguyen Bao Le ; Truong, Tuyen Ngoc
  • Subjects: Aldehydes ; Alkylation ; Antibacterial materials ; Anticancer properties ; Chemical synthesis ; Chemistry ; Coliforms ; E coli ; Sodium metabisulfite
  • Is Part Of: RSC advances, 2023, Vol.13 (1), p.399-420
  • Description: Compounds containing benzimidazole moiety occupy privileged chemical space for discovering new bioactive substances. In continuation of our recent work, 69 benzimidazole derivatives were designed and synthesized with good to excellent yields of 46–99% using efficient synthesis protocol i.e. sodium metabisulfite catalyzed condensation of aromatic aldehydes with o-phenylenediamines to form 2-arylbenzimidazole derivatives followed by N-alkylation by conventional heating or microwave irradiation for diversification. Potent antibacterial compounds against MSSA and MRSA were discovered such as benzimidazole compounds 3k (2-(4-nitrophenyl), N-benzyl), 3l (2-(4-chlorophenyl), N-(4-chlorobenzyl)), 4c (2-(4-chlorophenyl), 6-methyl, N-benzyl), 4g (2-(4-nitrophenyl), 6-methyl, N-benzyl), and 4j (2-(4-nitrophenyl), 6-methyl, N-(4-chlorobenzyl)) with MIC of 4–16 μg mL−1. In addition, compound 4c showed good antimicrobial activities (MIC = 16 μg mL−1) against the bacteria strains Escherichia coli and Streptococcus faecalis. Moreover, compounds 3k, 3l, 4c, 4g, and 4j have been found to kill HepG2, MDA-MB-231, MCF7, RMS, and C26 cancer cells with low μM IC50 (2.39–10.95). These compounds showed comparable drug-like properties as ciprofloxacin, fluconazole, and paclitaxel in computational ADMET profiling. Finally, docking studies were used to assess potential protein targets responsible for their biological activities. Especially, we found that DHFR is a promising target both in silico and in vitro with compound 4c having IC50 of 2.35 μM.
  • Publisher: Cambridge: Royal Society of Chemistry
  • Language: English
  • Identifier: ISSN: 2046-2069
    EISSN: 2046-2069
    DOI: 10.1039/d2ra06667j
  • Source: DOAJ Directory of Open Access Journals
    PubMed Central
    SWEPUB Freely available online
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