Synthesis and biological activity of imidazole based 1,4-naphthoquinones

• Published in: New journal of chemistry 2020-05, Vol.44 (17), p.6889-691
• Main Authors: Choudhari, Dinkar, Salunke-Gawali, Sunita, Chakravarty, Debamitra, Shaikh, Samir R, Lande, Dipali N, Gejji, Shridhar P, Rao, Pradeep Kumar, Satpute, Surekha, Puranik, Vedavati G, Gonnade, Rajesh
• Format: Article
• Language: English
• Subjects: Biological activity; Charge distribution; Crystal structure; Crystallography; Density functional theory; Derivatives; Electronic structure; Fungicides; Imidazole; NMR; Nuclear magnetic resonance; Single crystals
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/c9nj04339j

Design and development of drugs in multi-drug resistant (MDR) infections have been of growing interest. We report the syntheses, and antibacterial and antifungal activities of imidazole-based 1,4-naphthoquinones ( I-1 to I-4 ; 1-alkyl-2-methyl-1 H -naphtho[2,3- d ]imidazole-4,9-dione (alkyl = methyl to butyl)) and their precursors ( B-3 ; N -(3-chloro-1,-dioxo-1,4-dihydronaphthalen-2-yl)acetamide) and A-1 to A-4 ; N -(3-(alkylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide (alkyl = methyl to butyl). Crystal structures of B-3 , A-1 to A-3 and I-2 to I-4 were obtained through single crystal X-ray diffraction experiments. Electronic structure and charge distribution have further been characterized with the use of Density Functional Theory. Seven of these derivatives display a broad spectrum of antibacterial activity against few selected bacterial strains (Gram-positive and Gram-negative). As demonstrated MIC values with B-2 and B-3 against bacterial isolates were 8-64 μg ml −1 and those against pathogenic yeast, C. albicans , were observed in the range of 128-256 μg ml −1 . MIC data of these derivatives suggest them to be promising against pathogens. Design and development of drugs in multi-drug resistant (MDR) infections have been of growing interest. The syntheses, structural studies, antibacterial and antifungal activities of imidazole-based 1,4-naphthoquinones are studied in this investigation.