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

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/7997/1/fist-2015-nadeem-Synthesis%20of%20N-Substituted.pdf http://umpir.ump.edu.my/id/eprint/7997/ http://www.ajol.info/index.php/tjpr/article/view/119561
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spelling	my.ump.umpir.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
institution	Universiti Malaysia Pahang
building	UMP Library
collection	Institutional Repository
continent	Asia
country	Malaysia
content_provider	Universiti Malaysia Pahang
content_source	UMP Institutional Repository
url_provider	http://umpir.ump.edu.my/
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/7997/1/fist-2015-nadeem-Synthesis%20of%20N-Substituted.pdf http://umpir.ump.edu.my/id/eprint/7997/ http://www.ajol.info/index.php/tjpr/article/view/119561
_version_	1643665769607725056
score	13.211869

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

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