Synthesis, Characterization, and Biological Evaluation of Some New Functionalized Terphenyl Derivatives

Abstract

New functionalized terphenyl derivatives incorporating various heterocyclic rings are prepared by using 4,4′′-difluoro-5′-hydroxy-1,1′:3′,1′′-terphenyl-4′-carbohydrazide as a key intermediate derived from 4,4′-difluoro chalcone, a versatile synthone. All the derivatives are characterized by 1H NMR, IR, and mass spectral data. All the synthesized products are screened for their in vitro antimicrobial and antioxidant properties. The majority of the tested compounds exhibited significant antioxidant activity and some of them showed good antimicrobial activity.

2-{[5-(Diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide

“…The other M800 (Page 3) intermediate, 5-(diphenylmethyl)-1,3,4-oxadiazole-2(3H)-thione 3 was synthesized by adopting the method described in our earlier work [19].…”

2'-[(4-Fluorophenyl)carbonyl]-1'-phenyl-1',2',5',6',7',7a'-hexahydrospiro[indole-3,3'-pyrrolizin]-2(1H)-one

“…Chalcones are highly reactive substances of varied nature. The basic skeleton of chalcones which possess α,β-unsaturated carbonyl group is useful as the starting material for the synthesis of various biodynamic heterocyclic compounds such as pyrazolines, isoxazolines, pyridines, pyrimidines, benzodiazepines and cyclohexenone derivatives [7][8][9][10][11]. In addition, multicomponent reactions of chalcones with various components yield 2,4,6-triaryl pyridines [12], spiro pyrrolizines [13][14][15], cyanopyridines [16] etc.…”

Cytotoxic and Antimicrobial Activity of Dehydrozingerone based Cyclopropyl Derivatives

“…Enone system of chalcones is almost planar with trans ‐double bond. This structure enables various transformations of enone system, which undergo cyclization reactions with urea, thiourea, hydroxylamine, hydrazine, guanidine, forming heterocyclic unit between aromates, and active methylenic compounds (malononitrile, esters of cyanoacetic and acetoacetic acid, acetylacetone, nitromethane . Sole double bond of enone system is reactive toward Michael initiated ring closure (MIRC) as well as the sulfoxonium salts ( Corey–Chaykovsky reaction), yielding cyclopropane derivatives.…”