Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents

Purpose: To evaluate antibacterial activity of a series of molecules bearing 1,3,4-oxadiazole and azomethine moieties. Methods: The 4-chlorobenzoic acid (1) was precursor to N'-substituted-2-(5-(4-chlorophenyl)-1,3,4- oxadiazol-2-ylthio)acetohydrazide, 8a-p, through a multistep synthesis of co...

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Main Authors:	Akhtar, Muhammad Nadeem, Rasool, Shahid, Rehman, Aziz-ur, Abbasi, Muhammad Athar
Format:	Article
Language:	English
Published:	Pharmacotherapy Group 2015
Subjects:	QD Chemistry
Online Access:	http://umpir.ump.edu.my/id/eprint/7997/ http://umpir.ump.edu.my/id/eprint/7997/ http://umpir.ump.edu.my/id/eprint/7997/ http://umpir.ump.edu.my/id/eprint/7997/1/fist-2015-nadeem-Synthesis%20of%20N-Substituted.pdf

id	ump-7997
recordtype	eprints
spelling	ump-79972018-04-18T04:06:56Z http://umpir.ump.edu.my/id/eprint/7997/ Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents Akhtar, Muhammad Nadeem Rasool, Shahid Rehman, Aziz-ur Abbasi, Muhammad Athar QD Chemistry Purpose: To evaluate antibacterial activity of a series of molecules bearing 1,3,4-oxadiazole and azomethine moieties. Methods: The 4-chlorobenzoic acid (1) was precursor to N'-substituted-2-(5-(4-chlorophenyl)-1,3,4- oxadiazol-2-ylthio)acetohydrazide, 8a-p, through a multistep synthesis of corresponding ester, 2, hydrazide, 3 and 1,3,4-oxadiazole, 4. The molecule, 4, was subjected to electrophilic substitution by ethyl-2-bromoacetate to yield 5 which was stepped to 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2- ylthio)acetohydrazide (6). The target molecules, 8a-p, were synthesized by nucleophilic addition of 6 to arylaldehydes, 7a-p. The proposed structures of all the synthesized molecules were elucidated by Infra Red (IR), Proton Nuclear Magnetic Resonance (1H-NMR) and Electron Impact Mass Spectrometry (EIMS) spectral data. Antibacterial activity was evaluated by the principle that microbial growth is in a log phase of growth and so results in increased absorbance of broth medium which is observed. Results: The molecule, 8b, was active against S. aureus and 8c against S. typhi only. The molecule, 8p, was the most active against S. typhi with minimum inhibitory concentration (MIC) value of 10.04 ± 1.25 μM while 8e was active against E. coli with MIC of 9.45 ± 1.00 μM, both relative to the reference standard, ciprofloxacin, which displayed MIC of 9.13 ± 2.00 and 8.90 ± 1.65 μM, respectively. Conclusion: Most of the synthesized molecules exhibit 50 % antibacterial activity relative to the reference. Molecules 8b and 8c are the least active compounds. Pharmacotherapy Group 2015 Article PeerReviewed application/pdf en http://umpir.ump.edu.my/id/eprint/7997/1/fist-2015-nadeem-Synthesis%20of%20N-Substituted.pdf Akhtar, Muhammad Nadeem and Rasool, Shahid and Rehman, Aziz-ur and Abbasi, Muhammad Athar (2015) Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents. Tropical Journal of Pharmaceutical Research, 14 (6). pp. 1081-1088. ISSN 1596-5996 (print); 1596-9827 (online) http://www.ajol.info/index.php/tjpr/article/view/119561 doi: 10.4314/tjpr.v14i6.21
repository_type	Digital Repository
institution_category	Local University
institution	Universiti Malaysia Pahang
building	UMP Institutional Repository
collection	Online Access
language	English
topic	QD Chemistry
spellingShingle	QD Chemistry Akhtar, Muhammad Nadeem Rasool, Shahid Rehman, Aziz-ur Abbasi, Muhammad Athar Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents
description	Purpose: To evaluate antibacterial activity of a series of molecules bearing 1,3,4-oxadiazole and azomethine moieties. Methods: The 4-chlorobenzoic acid (1) was precursor to N'-substituted-2-(5-(4-chlorophenyl)-1,3,4- oxadiazol-2-ylthio)acetohydrazide, 8a-p, through a multistep synthesis of corresponding ester, 2, hydrazide, 3 and 1,3,4-oxadiazole, 4. The molecule, 4, was subjected to electrophilic substitution by ethyl-2-bromoacetate to yield 5 which was stepped to 2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2- ylthio)acetohydrazide (6). The target molecules, 8a-p, were synthesized by nucleophilic addition of 6 to arylaldehydes, 7a-p. The proposed structures of all the synthesized molecules were elucidated by Infra Red (IR), Proton Nuclear Magnetic Resonance (1H-NMR) and Electron Impact Mass Spectrometry (EIMS) spectral data. Antibacterial activity was evaluated by the principle that microbial growth is in a log phase of growth and so results in increased absorbance of broth medium which is observed. Results: The molecule, 8b, was active against S. aureus and 8c against S. typhi only. The molecule, 8p, was the most active against S. typhi with minimum inhibitory concentration (MIC) value of 10.04 ± 1.25 μM while 8e was active against E. coli with MIC of 9.45 ± 1.00 μM, both relative to the reference standard, ciprofloxacin, which displayed MIC of 9.13 ± 2.00 and 8.90 ± 1.65 μM, respectively. Conclusion: Most of the synthesized molecules exhibit 50 % antibacterial activity relative to the reference. Molecules 8b and 8c are the least active compounds.
format	Article
author	Akhtar, Muhammad Nadeem Rasool, Shahid Rehman, Aziz-ur Abbasi, Muhammad Athar
author_facet	Akhtar, Muhammad Nadeem Rasool, Shahid Rehman, Aziz-ur Abbasi, Muhammad Athar
author_sort	Akhtar, Muhammad Nadeem
title	Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents
title_short	Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents
title_full	Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents
title_fullStr	Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents
title_full_unstemmed	Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents
title_sort	synthesis of n'-substituted-2-((5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio acetohydrazie derivatives as suitable antibacterial agents
publisher	Pharmacotherapy Group
publishDate	2015
url	http://umpir.ump.edu.my/id/eprint/7997/ http://umpir.ump.edu.my/id/eprint/7997/ http://umpir.ump.edu.my/id/eprint/7997/ http://umpir.ump.edu.my/id/eprint/7997/1/fist-2015-nadeem-Synthesis%20of%20N-Substituted.pdf
first_indexed	2023-09-18T22:05:13Z
last_indexed	2023-09-18T22:05:13Z
_version_	1777414663166754816

Synthesis of N'-Substituted-2-((5-(4-Chlorophenyl)-1,3,4-Oxadiazol-2-ylthio Acetohydrazie Derivatives as Suitable Antibacterial Agents

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