Molecular hybrids integrated with benzimidazole and pyrazole structural motifs: design, synthesis, biological evaluation, and molecular docking studies

Ramar Sivaramakarthikeyan, Shunmugam Iniyaval, Vadivel Saravanan, Wei-Meng Lim, Chun-Wai Mai, Chennan Ramalingan

Research output: Contribution to journalArticleResearchpeer-review

41 Citations (Scopus)

Abstract

Synthesis of a series of benzimidazole-ornamented pyrazoles, 6a-6j has been obtained from arylhydrazine and aralkyl ketones via a multistep synthetic strategy. Among them, a hybrid-possessing para-nitrophenyl moiety connected to a pyrazole scaffold (6a) exerted the highest anti-inflammatory activity, which is superior to the standard, diclofenac sodium. While executing the 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity, a hybrid-possessing para-bromophenyl unit integrated at the pyrazole structural motif (6i) exhibited the highest activity among the hybrids examined. Besides, evaluation of anticancer potency of the synthesized hybrids revealed that the one containing a para-fluorophenyl unit tethered at the pyrazole nucleus (6h) showed the highest activity against both the pancreatic cancer cells (SW1990 and AsPCl) investigated. Considerable binding affinity between B-cell lymphoma and the hybrid, 6h has been reflected while performing molecular docking studies (-8.65 kcal/mol). The outcomes of the investigation expose that these hybrids could be used as effective intermediates to construct more potent biological agents.

Original languageEnglish
Pages (from-to)10089-10098
Number of pages10
JournalACS Omega
Volume5
Issue number17
DOIs
Publication statusPublished - 5 May 2020
Externally publishedYes

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