Novel 4‐Heteroaryl‐antipyrines: Synthesis, Molecular Docking, and Evaluation as Potential Anti‐breast Cancer Agents. (30th August 2018)

• Record Type: Journal Article
• Authors: Tao, Ziqi; Gomha, Sobhi M.; Badrey, Mohamed G.; El‐Idreesy, Tamer T.; Eldebss, Taha M. A.
• Is Part Of: Journal of heterocyclic chemistry. Volume 55:Number 10(2018)
• Page Start: 2408
• Page End: 2416
• Publication Date: 2018-08-30
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.3305
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : Reaction of 1‐[4‐(1, 2‐dihydro‐1, 5‐dimethyl‐2‐phenyl‐3‐oxo‐3 H ‐pyrazol‐4‐yl)‐2‐phenylsulfonyl‐1‐ethanone (1 ) with phenyl isothiocyanate afforded the 4‐(3‐mercapto‐3‐(phenylamino)‐2‐(phenylsulfonyl)acryloyl)‐1, 5‐dimethyl‐2‐phenyl‐1 H ‐pyrazol‐3(2 H )‐one (2 ). Treatment of compound2 with hydrazonoyl chlorides3a –h afforded the corresponding1, 3, 4‐thiadiazole derivatives5a –h . Cyclocondensation reaction of compound2 with the appropriate α‐halo‐compounds6, 8, 10, 12a, b or14 (ethyl 2‐chloroacetate, chloroacetonitrile, 1‐chloropropan‐2‐one, 2‐bromo‐1‐phenylethanone, 2‐bromo‐1‐ p ‐tolylethanone, and 2‐bromoacetyl‐3 H ‐benzo [f]chromen‐3‐one) afforded the 1, 3‐thiazole derivatives7, 9, 11, 13a, b, and15, respectively. Coupling of the ketosulphone1 with the appropriate diazotized 4 H ‐1, 2, 4‐triazol‐3‐amine16 and 2‐aminobenzimidazole19 afforded triazolo[5, 1‐c][1, 2, 4]triazine18 and benzo[4, 5]imidazo[2, 1‐c][1, 2, 4]triazine21, respectively. The structures of the synthesized compounds were confirmed on the basis of their elemental analysis and spectral data and evaluated as potential anti‐breast cancer agents. Moreover, the computational studies using MOE 2014.09 software are confirming the results in biological activity. Abstract :