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

Abstract

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 Gramnegative 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.

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

“…Recently, antimicrobial activities of 1,4‐naphthoquinone derivatives have attracted much attention ,. Pingaew et al .…”

“…Recently, antimicrobial activities of 1,4-naphthoquinone derivatives have attracted much attention. [15,16] Pingaew et al [17] reported the synthesis of novel 1,4-naphthoquinone-based sulfonamides and antimicrobial and anticancer potentials (compound I). Cardoso et al [18] performed the synthesis and antibacterial evaluation of sulfonamide-based lapachone derivatives (compound II).…”

Synthesis and antimicrobial evaluation of promising 7-arylamino-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylates and their halogenated amino compounds for treating Gram-negative bacterial infections

“…19,20 Naturally occurring quinones are well-known as clinically useful drugs for treating cancer. 21 Although most of the quinone derivatives show a potential cytotoxic prole against a number of cancer cell lines, 22 they are still associated with other pharmacological activities, such as antibacterial, 23 antifungal, 24 antiviral, 25 anti-inammatory, 26 and antimalarial. 27 The literature about the rational design of antimicrobials describes several aminoquinone compounds 28,29 (1-6) and halo-1,4-naphtoquinone derivatives 30 (7-8) with promising inhibitory effects against pathogenic bacteria ( Fig.…”

Efficient amidation of weak amines: synthesis, chiral separation by SFC, and antimicrobial activity of N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) carboxamide

“…In this direction, six bacterial pathogens such as V. cholera, S. typhi, P. aeruginosa, R. rhodochrous, M. smegmatis, and M. luteus were identified. Based on the promising antibacterial and antimicrobial activities exhibited by anthraquinones and proline [27][28][29] derivatives, we considered antibacterial activity for some representative amides synthesised by us. Minimum inhibitory concentration (MIC) values of the synthesized compounds (−)-4a, (+)-4a′, (−)-4b and (+)-4b′ were examined by microdilution plate assay against six bacterial pathogenic strains consisting of three Gram-positive and three Gram-negative strains.…”