Molecular Hybrids Integrated with Benzimidazole and Pyrazole Structural Motifs: Design, Synthesis, Biological Evaluation, and Molecular Docking Studies | Zendy

Ramar Sivaramakarthikeyan | Zendy; Shunmugam Iniyaval | Zendy; Vadivel Saravanan | Zendy; WeiMeng Lim | Zendy; ChunWai Mai | Zendy; Chennan Ramalingan | Zendy

Open Access

Molecular Hybrids Integrated with Benzimidazole and Pyrazole Structural Motifs: Design, Synthesis, Biological Evaluation, and Molecular Docking Studies

Author(s) -

Ramar Sivaramakarthikeyan,

Shunmugam Iniyaval,

Vadivel Saravanan,

WeiMeng Lim,

ChunWai Mai,

Chennan Ramalingan

Publication year - 2020

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.0c00630

Subject(s) - pyrazole , benzimidazole , chemistry , moiety , hybrid , stereochemistry , diclofenac sodium , docking (animal) , structural motif , combinatorial chemistry , biological activity , rational design , structure–activity relationship , biochemistry , in vitro , organic chemistry , biology , genetics , medicine , botany , nursing , chromatography

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.

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