Design, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation

A series of 6-(morpholinosulfonyl)quinoxalin-2(1H)-one based hydrazone, hydrazine, and pyrazole moieties were designed, synthesized, and evaluated for their in vitro antimicrobial activity. All the synthesized quinoxaline derivatives were characterized by IR, NMR (1H /13C), and EI MS. The results di...

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Autores principales:	Ahmed Ragab, Doaa M. Elsisi, Ola A. Abu Ali, Moustafa S. Abusaif, Ahmed A. Askar, Awatef A. Farag, Yousry A. Ammar
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2022
Materias:	Quinoxaline derivatives, Antimicrobial activity MIC, MBC and MFC Multi-drug resistance bacteria (MDRB) DNA gyrase In silico ADME and molecular docking Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/9c96fd9f9736450982119d8ffe59f359
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spelling	oai:doaj.org-article:9c96fd9f9736450982119d8ffe59f3592021-11-04T04:27:43ZDesign, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation1878-535210.1016/j.arabjc.2021.103497https://doaj.org/article/9c96fd9f9736450982119d8ffe59f3592022-01-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S1878535221005128https://doaj.org/toc/1878-5352A series of 6-(morpholinosulfonyl)quinoxalin-2(1H)-one based hydrazone, hydrazine, and pyrazole moieties were designed, synthesized, and evaluated for their in vitro antimicrobial activity. All the synthesized quinoxaline derivatives were characterized by IR, NMR (1H /13C), and EI MS. The results displayed good to moderate antimicrobial potential against six bacterial, and two fungal standard strains. Among the tested derivatives, six quinoxalin-2(1H)-one derivatives 4a, 7, 8a, 11b, 13, and 16 exhibited a significant antibacterial activity with MIC values (0.97–62.5 µg/mL), and MBC values (1.94–88.8 µg/mL) compared with Tetracycline (MICs = 15.62–62.5 µg/mL, and MBCs = 18.74–93.75 µg/mL), and Amphotericin B (MICs = 12.49–88.8 µg/mL, and MFC = 34.62–65.62 µg/mL). In addition, according to CLSI standards, the most active quinoxalin-2(1H)-one derivatives demonstrated bactericidal and fungicidal behavior. Moreover, the most active quinoxaline derivatives showed a considerable antibacterial activity with bactericidal potential against multi-drug resistance bacteria (MDRB) strains with MIC values ranged between (1.95–15.62 µg/mL), and MBC values (3.31–31.25 µg/mL) near to standard Norfloxacin (MIC = 0.78–3.13 µg/mL, and MBC = 1.4–5.32 µg/mL. Further, in vitro S. aureus DNA gyrase inhibition activity were evaluated for the promising derivatives and displayed potency with IC50 values (10.93 ± 1.81–26.18 ± 1.22 µM) compared with Ciprofloxacin (26.31 ± 1.64 µM). Interestingly, these derivatives revealed as good immunomodulatory agents by a percentage ranging between 82.8 ± 0.37 and 142.4 ± 0.98 %. Finally, some in silico ADME, toxicity prediction, and molecular docking simulation were performed and showed a promising safety profile with good binding mode.Ahmed RagabDoaa M. ElsisiOla A. Abu AliMoustafa S. AbusaifAhmed A. AskarAwatef A. FaragYousry A. AmmarElsevierarticleQuinoxaline derivatives, Antimicrobial activityMIC, MBC and MFCMulti-drug resistance bacteria (MDRB)DNA gyraseIn silico ADME and molecular dockingChemistryQD1-999ENArabian Journal of Chemistry, Vol 15, Iss 1, Pp 103497- (2022)
institution	DOAJ
collection	DOAJ
language	EN
topic	Quinoxaline derivatives, Antimicrobial activity MIC, MBC and MFC Multi-drug resistance bacteria (MDRB) DNA gyrase In silico ADME and molecular docking Chemistry QD1-999
spellingShingle	Quinoxaline derivatives, Antimicrobial activity MIC, MBC and MFC Multi-drug resistance bacteria (MDRB) DNA gyrase In silico ADME and molecular docking Chemistry QD1-999 Ahmed Ragab Doaa M. Elsisi Ola A. Abu Ali Moustafa S. Abusaif Ahmed A. Askar Awatef A. Farag Yousry A. Ammar Design, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation
description	A series of 6-(morpholinosulfonyl)quinoxalin-2(1H)-one based hydrazone, hydrazine, and pyrazole moieties were designed, synthesized, and evaluated for their in vitro antimicrobial activity. All the synthesized quinoxaline derivatives were characterized by IR, NMR (1H /13C), and EI MS. The results displayed good to moderate antimicrobial potential against six bacterial, and two fungal standard strains. Among the tested derivatives, six quinoxalin-2(1H)-one derivatives 4a, 7, 8a, 11b, 13, and 16 exhibited a significant antibacterial activity with MIC values (0.97–62.5 µg/mL), and MBC values (1.94–88.8 µg/mL) compared with Tetracycline (MICs = 15.62–62.5 µg/mL, and MBCs = 18.74–93.75 µg/mL), and Amphotericin B (MICs = 12.49–88.8 µg/mL, and MFC = 34.62–65.62 µg/mL). In addition, according to CLSI standards, the most active quinoxalin-2(1H)-one derivatives demonstrated bactericidal and fungicidal behavior. Moreover, the most active quinoxaline derivatives showed a considerable antibacterial activity with bactericidal potential against multi-drug resistance bacteria (MDRB) strains with MIC values ranged between (1.95–15.62 µg/mL), and MBC values (3.31–31.25 µg/mL) near to standard Norfloxacin (MIC = 0.78–3.13 µg/mL, and MBC = 1.4–5.32 µg/mL. Further, in vitro S. aureus DNA gyrase inhibition activity were evaluated for the promising derivatives and displayed potency with IC50 values (10.93 ± 1.81–26.18 ± 1.22 µM) compared with Ciprofloxacin (26.31 ± 1.64 µM). Interestingly, these derivatives revealed as good immunomodulatory agents by a percentage ranging between 82.8 ± 0.37 and 142.4 ± 0.98 %. Finally, some in silico ADME, toxicity prediction, and molecular docking simulation were performed and showed a promising safety profile with good binding mode.
format	article
author	Ahmed Ragab Doaa M. Elsisi Ola A. Abu Ali Moustafa S. Abusaif Ahmed A. Askar Awatef A. Farag Yousry A. Ammar
author_facet	Ahmed Ragab Doaa M. Elsisi Ola A. Abu Ali Moustafa S. Abusaif Ahmed A. Askar Awatef A. Farag Yousry A. Ammar
author_sort	Ahmed Ragab
title	Design, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation
title_short	Design, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation
title_full	Design, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation
title_fullStr	Design, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation
title_full_unstemmed	Design, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation
title_sort	design, synthesis of new novel quinoxalin-2(1h)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico adme and molecular docking simulation
publisher	Elsevier
publishDate	2022
url	https://doaj.org/article/9c96fd9f9736450982119d8ffe59f359
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Design, synthesis of new novel quinoxalin-2(1H)-one derivatives incorporating hydrazone, hydrazine, and pyrazole moieties as antimicrobial potential with in-silico ADME and molecular docking simulation

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