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N,2,6-Trisubstitute...
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
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- Pham, Em Canh (author)
- Hong Bang Int Univ, Fac Pharm, Dept Med Chem, Ho Chi Minh City 700000, Vietnam.
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- Thi, Tuong Vi Le (author)
- City Childrens Hosp, Fac Pharm, Dept Pharmacol Clin Pharm, Ho Chi Minh City 700000, Vietnam.;Tra Vinh Univ, Fac Pharm, Dept Organ Chem, Tra Vinh, Vietnam.
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Hong, Huong Ha Ly (author)
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- Thi, Bich Ngoc Vo (author)
- Hong Bang Int Univ, Fac Pharm, Dept Pharmacognosy & Bot, Ho Chi Minh City 700000, Vietnam.
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- Vong, Long B. (author)
- Int Univ, Sch Biomed Engn, Ho Chi Minh City 700000, Vietnam.;Vietnam Natl Univ Ho Chi Minh City VNU HCM, Ho Chi Minh 700000, Vietnam.
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- Vu, Thao Thanh (author)
- Univ Med & Pharm Ho Chi Minh City, Fac Pharm, Dept Microbiol Parasitol, Ho Chi Minh City 700000, Vietnam.
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- Vo, Duc Duy (author)
- Uppsala universitet,Organisk kemi,Beräkningsbiologi och bioinformatik,Tra Vinh Univ, Tra Vinh, Vietnam.
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- Nguyen, Ngoc Vi (author)
- Tra Vinh Univ, Fac Pharm, Dept Organ Chem, Tra Vinh, Vietnam.
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- Le, Khanh Nguyen Bao (author)
- Tra Vinh Univ, Fac Pharm, Dept Organ Chem, Tra Vinh, Vietnam.
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- Truong, Tuyen Ngoc (author)
- Tra Vinh Univ, Fac Pharm, Dept Organ Chem, Tra Vinh, Vietnam.
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Hong Bang Int Univ, Fac Pharm, Dept Med Chem, Ho Chi Minh City 700000, Vietnam City Childrens Hosp, Fac Pharm, Dept Pharmacol Clin Pharm, Ho Chi Minh City 700000, Vietnam.;Tra Vinh Univ, Fac Pharm, Dept Organ Chem, Tra Vinh, Vietnam. (creator_code:org_t)
- 2023
- 2023
- English.
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In: RSC Advances. - : Royal Society of Chemistry. - 2046-2069. ; 13:1, s. 399-420
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Abstract
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- 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 mu g mL(-1). In addition, compound 4c showed good antimicrobial activities (MIC = 16 mu g 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 mu M 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 mu M.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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- art (subject category)
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Pham, Em Canh
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Thi, Tuong Vi Le
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Hong, Huong Ha L ...
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Thi, Bich Ngoc V ...
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Vong, Long B.
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Vu, Thao Thanh
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Vo, Duc Duy
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Nguyen, Ngoc Vi
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Le, Khanh Nguyen ...
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Truong, Tuyen Ng ...
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- About the subject
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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and Organic Chemistr ...
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RSC Advances
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Uppsala University