Synthesis, molecular docking and antibacterial evaluation of new 1,4-naphthoquinone derivatives contains carbazole-6,11-dione moiety

• Published in: Journal of chemical biology 2014-07, Vol.7 (3), p.93-101
• Main Authors: Ravichandiran, P., Premnath, D., Vasanthkumar, S.
• Format: Article
• Language: English
• Subjects: Bacillus subtilis; Bacteria; Biochemistry; Biological and Medical Physics; Biophysics; Cell Biology; Chemistry; Chemistry and Materials Science; Molecules; Original; Original Article; Pharmacology/Toxicology; Physical Chemistry
• ISSN: 1864-6158; 1864-6166
• DOI: 10.1007/s12154-014-0115-z

A new series of new 1,4-naphthoquinone derivatives containing carbazole-6,11-dione moiety, which has not been reported yet, has been synthesized from 1,4-naphthoquinone and 4-aminophenylsulfone involving a Michael addition, benzoylation, and Pd-catalyzed coupling. This set of compounds has been evaluated for in vitro antibacterial studies against different Gram-positive and Gram-negative bacteria, and most of the synthesized compounds exhibited good antibacterial activity and the minimum inhibitory concentrations (MICs) are compared with the standard drugs used. Compound 7 exhibited good antibacterial activity among all the molecules studied with the best MIC of 2.1 μg/mL against Bacillus subtilis . To understand the molecular interactions with targeted proteins, the molecular docking of all the synthesized compounds were carried out; between 14 molecules docked, compound 7 was the one with the best glide and E model score of −7.73 and −95.37, respectively. In all docked molecules, compound 5 exhibited least glide and E model score of −4.55 and −101.56, respectively. Figure ᅟ