Design, Synthesis, and Characterization of Quinoxaline Derivatives as a Potent Antimicrobial Agent

Abstract

A series of quinoxalinone derivatives were synthesized by the reaction of o‐phenylenediamine with oxalic acid to yield 1, 4‐dihydro quinoxaline‐2, 3‐dione (1) and then treated with thionyl chloride to yield 2, 3 dichloro quinoxaline (2). This was further reacted with hydrazine hydrate to produce 2, 3‐dihydrazinyl quinoxaline (3). This was finally reacted with substituted aromatic aldehydes to produce 2,3‐bis[2‐(sustituted benzylidine) hydrazinyl] quinoxalines (4). These quinoxalinone derivatives were characterized by infrared spectroscopy and nuclear magnetic resonance spectroscopy and MASS spectral data. All the synthesized compounds were evaluated for their antimicrobial activity. The results of the antimicrobial study revealed that compounds 4c, 4d, and 4i were active and exhibited better inhibitory activities as compared to standard drug ciprofloxacin. The results were further checked with protein legend interaction by using docking studies, and all the compounds exhibited good docking scores between −8.72 and −11.29 kcal/mol against dihydrofolate reductase protein fragment from Staphylococcus aureus (PDB ID‐4XE6). Among all compound, 4c has shown maximum docking score and found in agreement to in vitro studies.

A Stable Radical Anion of Quinoxalin-2(1H)-one in Aerial Dioxygen Activation under Wet-Condition

“…Their extensive applications are recognized in the diverse areas of industry and pharmacology. [29][30] We then broadened our exploration, using the optimized reaction conditions for this aerobic oxygenation process. We began by investigating various substituents at the N-1 position of quinoxalin-2(1H)-ones (Figure 2).…”

A Review on Multipurpose Potential of Bioactive Heterocycle Quinoxaline

“…The binding energies of all the derivatives displayed good docking scores between −8.72 and −11.29 kcal/mol. Compounds 113 a (−11.29 kcal/mol), 113 b (−11.17 kcal/mol), and 113 c (−10.85 kcal/mol) were found to represent the most promising docking score as compared with the standard DHFR inhibitor ciprofloxacin (−7.57 kcal/mol) [63] …”

“…Compounds 113 a (À 11.29 kcal/mol), 113 b (À 11.17 kcal/mol), and 113 c (À 10.85 kcal/mol) were found to represent the most promising docking score as compared with the standard DHFR inhibitor ciprofloxacin (À 7.57 kcal/mol). [63] El-Attar et al, reported the design, synthesis and antibacterial evaluation of some novel quinoxaline derivatives targeting dihydropteroate synthase (DHPS) (114 and 115, Figure 33). Most of the synthesized compounds demonstrated good antibacterial activities against a panel of bacterial strains.…”

Visible-Light Promoted Regioselective Oxygenation of Quinoxalin-2(1H)-ones Using O2 as an Oxidant

“…Quinoxaline-2,3-diones belong to the category of many heterocycles and shown to have extensive applications in organic synthesis and material sciences. Their substantial utilization is also found in industry and pharmaceutics. − Due to their salient applications, developing convenient protocols for synthesizing quinoxaline-2,3-diones has become an important research topic. − Several reports are available to synthesize C-3 substituted quinoxalin-2­(1 H )-ones with diverse functionalities via direct C-3 functionalization. ,− The 3,4-dihydro-1,4-benzoxazin-2-one is an important heterocycle in organic synthesis and significantly used for C-3 functionalization. − …”