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

Pham, Em Canh; Thi, Tuong Vi Le; Hong, Huong Ha Ly; Thi, Bich Ngoc Vo; Vong, Long Binh; Vu, Thao Thanh; Vo, Duy Duc; Nguyen, Ngoc Vi Tran; Le, Khanh Nguyen Bao; Truong, Tuyen Ngoc

doi:10.1039/d2ra06667j

Cited by 17 publications

(3 citation statements)

References 52 publications

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“…All compounds showed binding in the active site of the enzyme. The 1,2,4-triazole ring of compounds 73a-73l is positioned almost perpendicular to the porphyrin plane, with a ring nitrogen (N-4) atom coordinated to the heme iron (Figure 10) [145,146]. Ahuja et al reported antifungal activity of compounds 74a-74c against F. verticillioides, D. oryzae, C. lunata, and F. fujikuroi (Figure 11).…”

Section: Kankate Et Al Reported the Synthesis Of Hybrids 73a-73l (Sch...mentioning

confidence: 99%

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

Marinescu

2023

Antibiotics

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Bacterial infections have attracted the attention of researchers in recent decades, especially due to the special problems they have faced, such as their increasing diversity and resistance to antibiotic treatment. The emergence and development of the SARS-CoV-2 infection stimulated even more research to find new structures with antimicrobial and antiviral properties. Among the heterocyclic compounds with remarkable therapeutic properties, benzimidazoles, and triazoles stand out, possessing antimicrobial, antiviral, antitumor, anti-Alzheimer, anti-inflammatory, analgesic, antidiabetic, or anti-ulcer activities. In addition, the literature of the last decade reports benzimidazole-triazole hybrids with improved biological properties compared to the properties of simple mono-heterocyclic compounds. This review aims to provide an update on the synthesis methods of these hybrids, along with their antimicrobial and antiviral activities, as well as the structure–activity relationship reported in the literature. It was found that the presence of certain groups grafted onto the benzimidazole and/or triazole nuclei (-F, -Cl, -Br, -CF3, -NO2, -CN, -CHO, -OH, OCH3, COOCH3), as well as the presence of some heterocycles (pyridine, pyrimidine, thiazole, indole, isoxazole, thiadiazole, coumarin) increases the antimicrobial activity of benzimidazole-triazole hybrids. Also, the presence of the oxygen or sulfur atom in the bridge connecting the benzimidazole and triazole rings generally increases the antimicrobial activity of the hybrids. The literature mentions only benzimidazole-1,2,3-triazole hybrids with antiviral properties. Both for antimicrobial and antiviral hybrids, the presence of an additional triazole ring increases their biological activity, which is in agreement with the three-dimensional binding mode of compounds. This review summarizes the advances of benzimidazole triazole derivatives as potential antimicrobial and antiviral agents covering articles published from 2000 to 2023.

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Section: Kankate Et Al Reported the Synthesis Of Hybrids 73a-73l (Sch...mentioning

confidence: 99%

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

Marinescu

2023

Antibiotics

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“…Cell culture and MTT assay according to our previous protocol. [18] Tumorsphere culture [19] An amount of 1,000 MCF-7 cells cultured in the low-attachment surface plate containing 100 μL of DMEMF12 medium (Gibco-Thermo Fisher Scientific, Waltham, MA, USA) and 20 nM epidermal growth factor and 20 nM fibroblast growth factor, (Sigma Aldrich, St. Louis, MO, USA)). The tumorsphere culture medium was added with 4 c at concentrations of 0, 10 and 40 μM.…”

Section: Representative Procedures For Hydrazide Synthesis Synthesis ...mentioning

confidence: 99%

Diarylether‐Amino Acid Conjugates as New Class of Anticancer Agents

et al. 2023

ChemistrySelect

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Diarylether (DE) is a privileged structure found in both natural products and synthetic compounds including small molecule drugs. We present the synthesis of a series of 13 new DE‐amino acid conjugates which were screened for cancer cells antiproliferation activity. Structure‐activity relationship suggests ester and phenyl groups in DE‐Phe‐OEt 4 c are important for the activity. Compound 4 c inhibited strongly MCF‐7 3D tumor sphere formation and have favourable calculated physical chemical properties according to Lipinski's rule of 5. Docking study suggests estrogen receptor and/ or 3a‐HSD type 3 protein could be the target(s) for anticancer activity of this class of compounds.

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“… 30 In MCRs, all the reactants are added simultaneously in a one-pot manner that generally results in reducing the cost and time-effective synthesis of the desired products. 31 …”

Section: Introductionmentioning

confidence: 99%

Synthesis, antioxidant activity, antimicrobial efficacy and molecular docking studies of 4-chloro-2-(1-(4-methoxyphenyl)-4,5-diphenyl-1H-imidazol-2-yl)phenol and its transition metal complexes

et al. 2023

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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

Abstract: The purpose of this study is to synthesize novel N,2,6-trisubstituted 1H-benzimidazole derivatives and evaluation of their antibacterial, antifungal, and anticancer activities as well as to study their mechanism of action.

Cited by 17 publications

References 52 publications

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

Benzimidazole-Triazole Hybrids as Antimicrobial and Antiviral Agents: A Systematic Review

Diarylether‐Amino Acid Conjugates as New Class of Anticancer Agents

Synthesis, antioxidant activity, antimicrobial efficacy and molecular docking studies of 4-chloro-2-(1-(4-methoxyphenyl)-4,5-diphenyl-1H-imidazol-2-yl)phenol and its transition metal complexes

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