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Synthesis, Molecular Properties Prediction and Antimicrobial Activity of Imidazolyl Schiff Bases, Triazoles and Azetidinones
Author(s) -
Rekha Tamatam,
Nagarjuna Ummadi,
Padmaja Adivireddy,
Padmavathi Venkatapuram
Publication year - 2019
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201900073
Subject(s) - chemistry , chloroacetyl chloride , aryl , nitro , medicinal chemistry , imine , cycloaddition , diazomethane , aromatization , triazole , stereochemistry , combinatorial chemistry , organic chemistry , chloride , catalysis , alkyl
Benzylidenehydrazinyl imidazoles ( 3 ) are prepared from 2‐hydrazinyl imidazoles ( 2 ) on treatment with hydrazine. The imine functionality in 3 is utilized to develop 5′‐aryl‐ N ‐(4‐aryl‐1 H ‐imidazol‐2‐yl)‐1 H ‐1,2,3‐triazol‐1‐amines ( 5 ) by 1,3‐dipolar cycloaddition of diazomethane followed by aromatization with I 2 in DMSO. Compounds 3 are also explored to prepare 4′‐aryl‐1‐(4‐aryl‐1 H ‐imidazol‐2‐ylamino)‐3‐chloroazetidin‐2‐ones ( 6 ) on treatment with chloroacetyl chloride. The Molinspiration calculations predicted that 3 , 5 and 6 have molecular hydrophobicity, conformational flexibility, good intestinal absorption and bioactivity scores. The chloro, bromo and nitro substituted imidazolyl azetidinones ( 6c , 6d , 6f ) and nitro substituted imidazolyl triazole ( 5f ) exhibited excellent antibacterial activity on B. subtilis , whereas chloro and nitro substituted imidazolyl triazoles ( 5c , 5f ) showed prominent antifungal activity on A. niger .