Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents

Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents

The synthetic methodology was initiated by reacting 1,4-benzodioxane-6-amine (1) with 2-bromoacetyl bromide (2) in aqueous alkaline media under dynamic pH control to get compound 2,3-dihydro-1,4-benzodioxin-6-yl-2-bromoacetamide (3). In the subsequent reactions, a variety of un/substituted-benzoic a...

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Published in:Pakistan Journal of Pharmaceutical Sciences
Main Author: Abbasi M.A.; Irshad M.; Aziz-Ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Shahid M.
Format: Article
Language:English
Published: Pakistan Journal of Pharmaceutical Sciences 2022
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85129100563&doi=10.36721%2fPJPS.2022.35.2.REG.447-456.1&partnerID=40&md5=3fccf1b8623d4db94192abdef8f91547
id 2-s2.0-85129100563
spelling 2-s2.0-85129100563
Abbasi M.A.; Irshad M.; Aziz-Ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Shahid M.
Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents
2022
Pakistan Journal of Pharmaceutical Sciences
35
2
10.36721/PJPS.2022.35.2.REG.447-456.1
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85129100563&doi=10.36721%2fPJPS.2022.35.2.REG.447-456.1&partnerID=40&md5=3fccf1b8623d4db94192abdef8f91547
The synthetic methodology was initiated by reacting 1,4-benzodioxane-6-amine (1) with 2-bromoacetyl bromide (2) in aqueous alkaline media under dynamic pH control to get compound 2,3-dihydro-1,4-benzodioxin-6-yl-2-bromoacetamide (3). In the subsequent reactions, a variety of un/substituted-benzoic acids (4a-k), through a succession of three steps, was converted into respective oxadiazole nucleophiles, 7a-k. Finally, the targeted molecules, 8a-k, were obtained by reacting 7a-k with electrophile 3 in an aprotic polar solvent. These compounds were corroborated by spectral characterization like IR, EI-MS, 1H-NMR, and CHN analysis data. These molecules were screened for their antibacterial potential and most of them exhibited a potent activity. Moreover, their cytotoxicity was profiled through hemolytic activity and it was observed that majority of them was very modest in toxicity. © 2022 Pakistan Journal of Pharmaceutical Sciences. All rights reserved.
Pakistan Journal of Pharmaceutical Sciences
1011601X
English
Article
author Abbasi M.A.; Irshad M.; Aziz-Ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Shahid M.
spellingShingle Abbasi M.A.; Irshad M.; Aziz-Ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Shahid M.
Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents
author_facet Abbasi M.A.; Irshad M.; Aziz-Ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Shahid M.
author_sort Abbasi M.A.; Irshad M.; Aziz-Ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Shahid M.
title Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents
title_short Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents
title_full Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents
title_fullStr Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents
title_full_unstemmed Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents
title_sort Synthesis of novel N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-{[5-(un/substituted-phenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}acetamides as potent antibacterial agents
publishDate 2022
container_title Pakistan Journal of Pharmaceutical Sciences
container_volume 35
container_issue 2
doi_str_mv 10.36721/PJPS.2022.35.2.REG.447-456.1
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85129100563&doi=10.36721%2fPJPS.2022.35.2.REG.447-456.1&partnerID=40&md5=3fccf1b8623d4db94192abdef8f91547
description The synthetic methodology was initiated by reacting 1,4-benzodioxane-6-amine (1) with 2-bromoacetyl bromide (2) in aqueous alkaline media under dynamic pH control to get compound 2,3-dihydro-1,4-benzodioxin-6-yl-2-bromoacetamide (3). In the subsequent reactions, a variety of un/substituted-benzoic acids (4a-k), through a succession of three steps, was converted into respective oxadiazole nucleophiles, 7a-k. Finally, the targeted molecules, 8a-k, were obtained by reacting 7a-k with electrophile 3 in an aprotic polar solvent. These compounds were corroborated by spectral characterization like IR, EI-MS, 1H-NMR, and CHN analysis data. These molecules were screened for their antibacterial potential and most of them exhibited a potent activity. Moreover, their cytotoxicity was profiled through hemolytic activity and it was observed that majority of them was very modest in toxicity. © 2022 Pakistan Journal of Pharmaceutical Sciences. All rights reserved.
publisher Pakistan Journal of Pharmaceutical Sciences
issn 1011601X
language English
format Article
accesstype
record_format scopus
collection Scopus
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