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Water-Assisted Self-Aggregation of Benzimidazole and Triazole Adducts.

ABSTRACT: The manuscript revolves around an interesting observation of solidification of a solution of N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazole-4-yl)methyl)aniline (A6) in the NMR tube after around 12 h. Real-time images showed fibrillar and spherulitic growth with tip branching and side branching, which is thermoreversible. The compound under investigation is unique because it is synthesized to understand the anticancer activity with two pharmacophores, benzimidazole and triazole. Click chemistry is employed for in situ generation of triazole moiety on benzimidazole. Previously, benzimidazole-based compounds have shown self-aggregation-induced gel-like behavior because of hydrogen bonding and/or ?-? stacking interactions. In the present case, NMR titrations with D₂O addition showed two distinct changes in the chemical shift for methylene bridges (connecting benzimidazole and triazole ring) and ortho protons of the phenyl ring (attached to triazole ring). Interestingly, a single-crystal X-ray structure shows the absence of hydrogen bonds and ?-? stacking while in the presence of only two distinct close contacts, completely correlating NMR data discussed in detail. A similar "molecular origin" for self-aggregation is observed in seven other flexible but regioisomeric compounds, which were designed and synthesized for inducing hydrogen bonding through the removal of N-ethyl group and insertion of aniline and/or fluoro group.

SUBMITTER: Sahay II

PROVIDER: S-EPMC6648399 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Water-Assisted Self-Aggregation of Benzimidazole and Triazole Adducts.

Sahay Ishani I II Ghalsasi Prasanna S PS

ACS omega 20190107 1

The manuscript revolves around an interesting observation of solidification of a solution of N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazole-4-yl)methyl)aniline (A6) in the NMR tube after around 12 h. Real-time images showed fibrillar and spherulitic growth with tip branching and side branching, which is thermoreversible. The compound under investigation is unique because it is synthesized to understand the anticancer activity with two pharma ...[more]

PMID: 31459341

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Project description: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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Water-Assisted Self-Aggregation of Benzimidazole and Triazole Adducts.

Publications

Water-Assisted Self-Aggregation of Benzimidazole and Triazole Adducts.

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