Synthesis, In Vitro and In Silico Antibacterial Evaluation of 4, 5‐Dihydro‐1H‐Indazoles. Issue 29 (12th October 2017)

• Record Type: Journal Article
• Authors: Khan, Rasool; Shah, Faiza; Salman, Muhammad; Khan, Zahid; Tavman, Aydin
• Is Part Of: ChemistrySelect. Volume 2:Issue 29(2017)
• Page Start: 9364
• Page End: 9368
• Publication Date: 2017-10-12
• Subjects: 4, 5-dihydro-1H-indazole -- pentane-2, 4-dione -- 1, 5-diaryl -- 4-acetyl cyclohexen-3-one -- In-vitro anti-bacterial potential -- Docking studies; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201701244
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Synthesis and evaluation of in‐vitro and in‐silico anti‐bacterial potential of a series of 4, 5‐dihydro‐1 H ‐indazoles is reported here. The synthesis of the target 4, 5‐dihydro‐1 H‐ indazoles was accomplished by reacting 1, 5‐diaryl, 4‐acetyl cyclohexen‐3‐one with hydrazine hydrate and selected hydrazides. All the synthesized compounds were evaluated for their anti‐bacterial potential against Escherichia coli, Proteus vulgaris, Staphylococcus aureus and Salmonella typhimurium . Among the synthesized indazoles, N, N ‐dimethyl‐4‐(3‐methyl‐6‐phenyl‐4, 5‐dihydro‐1 H ‐indazol‐4‐yl)aniline and 3‐methyl‐4‐(3‐nitrophenyl)‐1, 6‐diphenyl‐4, 5‐dihydro‐1 H ‐indazole exhibited highest antimicrobial activity against Salmonella typhimurium i. e. MIC50 = 3.85 and 4.12 mg/ml respectively. Docking studies were also carried out to provide an insight into binding interaction with the active site of respective enzyme. Abstract : Starting from chalcone, 4, 5 dihydro 1‐H‐Indazole have been synthesized via an intermediate 1, 5‐diaryl, 4‐accetyl cyclohexen‐3‐one. Among the synthesized indazoles, N, N ‐dimethyl‐4‐(3‐methyl‐6‐phenyl‐4, 5‐dihydro‐1 H ‐indazol‐4‐yl)aniline (5 d) and 3‐methyl‐4‐(3‐nitrophenyl)‐1, 6‐diphenyl‐4, 5‐dihydro‐1 H ‐indazole (5 g) exhibited highest antimicrobial activity against Salmonella typhimurium .