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A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation

A highly convenient method has been developed for the synthesis of (prop-2-ynyloxy) benzene and its derivatives. Differently substituted phenol and aniline derivatives were allowed to react with propargyl bromide in the presence of K2CO3 base and acetone as solvent. The compounds were synthesized in...

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Main Authors: Batool, Tannaza, Rasool, Nasir, Gull, Yasmeen, Noreen, Mnaza, Nasim, Faiz-ul-Hassan, Yaqoob, Asma, Zubair, Muhammad, Rana, Usman Ali, Khan, Salah Ud-Din, Zia-Ul-Haq, Muhammad, Jaafar, Hawa Z. E.
Format: Article
Language:English
Published: Public Library of Science 2014
Online Access:http://psasir.upm.edu.my/id/eprint/36149/1/A%20convenient%20method%20for%20the%20synthesis%20of.pdf
http://psasir.upm.edu.my/id/eprint/36149/
http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0115457
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spelling my.upm.eprints.361492015-08-24T00:53:57Z http://psasir.upm.edu.my/id/eprint/36149/ A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation Batool, Tannaza Rasool, Nasir Gull, Yasmeen Noreen, Mnaza Nasim, Faiz-ul-Hassan Yaqoob, Asma Zubair, Muhammad Rana, Usman Ali Khan, Salah Ud-Din Zia-Ul-Haq, Muhammad Jaafar, Hawa Z. E. A highly convenient method has been developed for the synthesis of (prop-2-ynyloxy) benzene and its derivatives. Differently substituted phenol and aniline derivatives were allowed to react with propargyl bromide in the presence of K2CO3 base and acetone as solvent. The compounds were synthesized in good yields (53–85%). Low cost, high yields and easy availability of compounds helped in the synthesis. Electron withdrawing groups favor the formation of stable phenoxide ion thus in turn favors the formation of product while electron donating groups do not favor the reaction. Phenol derivatives gave good yields as compared to that of aniline. As aprotic polar solvents favor SN2 type reactions so acetone provided best solvation for the reactions. K2CO3 was proved to be good for the synthesis. Antibacterial, Antiurease and NO scavenging activity of synthesized compounds were also examined. 4-bromo-2-chloro-1-(prop-2-ynyloxy)benze​ne2a was found most active compound against urease enzyme with a percentage inhibition of 82.00±0.09 at 100 µg/mL with IC50 value of 60.2. 2-bromo-4-methyl-1-(prop-2-ynyloxy)benze​ne2d was found potent antibacterial against Bacillus subtillus showing excellent inhibitory action with percentage inhibition of 55.67±0.26 at 100 µg/ml wih IC50 value of 79.9. Based on results, it can be concluded that some of the synthesized compounds may have potential antiurease and antibacterial effects against several harmful substances. Public Library of Science 2014 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/36149/1/A%20convenient%20method%20for%20the%20synthesis%20of.pdf Batool, Tannaza and Rasool, Nasir and Gull, Yasmeen and Noreen, Mnaza and Nasim, Faiz-ul-Hassan and Yaqoob, Asma and Zubair, Muhammad and Rana, Usman Ali and Khan, Salah Ud-Din and Zia-Ul-Haq, Muhammad and Jaafar, Hawa Z. E. (2014) A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation. PLOS ONE, 9 (12). art. no. e115457. pp. 1-19. ISSN 1932-6203 http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0115457 10.1371/journal.pone.0115457
institution Universiti Putra Malaysia
building UPM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Putra Malaysia
content_source UPM Institutional Repository
url_provider http://psasir.upm.edu.my/
language English
description A highly convenient method has been developed for the synthesis of (prop-2-ynyloxy) benzene and its derivatives. Differently substituted phenol and aniline derivatives were allowed to react with propargyl bromide in the presence of K2CO3 base and acetone as solvent. The compounds were synthesized in good yields (53–85%). Low cost, high yields and easy availability of compounds helped in the synthesis. Electron withdrawing groups favor the formation of stable phenoxide ion thus in turn favors the formation of product while electron donating groups do not favor the reaction. Phenol derivatives gave good yields as compared to that of aniline. As aprotic polar solvents favor SN2 type reactions so acetone provided best solvation for the reactions. K2CO3 was proved to be good for the synthesis. Antibacterial, Antiurease and NO scavenging activity of synthesized compounds were also examined. 4-bromo-2-chloro-1-(prop-2-ynyloxy)benze​ne2a was found most active compound against urease enzyme with a percentage inhibition of 82.00±0.09 at 100 µg/mL with IC50 value of 60.2. 2-bromo-4-methyl-1-(prop-2-ynyloxy)benze​ne2d was found potent antibacterial against Bacillus subtillus showing excellent inhibitory action with percentage inhibition of 55.67±0.26 at 100 µg/ml wih IC50 value of 79.9. Based on results, it can be concluded that some of the synthesized compounds may have potential antiurease and antibacterial effects against several harmful substances.
format Article
author Batool, Tannaza
Rasool, Nasir
Gull, Yasmeen
Noreen, Mnaza
Nasim, Faiz-ul-Hassan
Yaqoob, Asma
Zubair, Muhammad
Rana, Usman Ali
Khan, Salah Ud-Din
Zia-Ul-Haq, Muhammad
Jaafar, Hawa Z. E.
spellingShingle Batool, Tannaza
Rasool, Nasir
Gull, Yasmeen
Noreen, Mnaza
Nasim, Faiz-ul-Hassan
Yaqoob, Asma
Zubair, Muhammad
Rana, Usman Ali
Khan, Salah Ud-Din
Zia-Ul-Haq, Muhammad
Jaafar, Hawa Z. E.
A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation
author_facet Batool, Tannaza
Rasool, Nasir
Gull, Yasmeen
Noreen, Mnaza
Nasim, Faiz-ul-Hassan
Yaqoob, Asma
Zubair, Muhammad
Rana, Usman Ali
Khan, Salah Ud-Din
Zia-Ul-Haq, Muhammad
Jaafar, Hawa Z. E.
author_sort Batool, Tannaza
title A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation
title_short A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation
title_full A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation
title_fullStr A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation
title_full_unstemmed A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation
title_sort convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation
publisher Public Library of Science
publishDate 2014
url http://psasir.upm.edu.my/id/eprint/36149/1/A%20convenient%20method%20for%20the%20synthesis%20of.pdf
http://psasir.upm.edu.my/id/eprint/36149/
http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0115457
_version_ 1643831663180906496
score 13.211869

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