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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


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


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.

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Additional Metadata

Item Type: Article
Divisions: Faculty of Agriculture
DOI Number: https://doi.org/10.1371/journal.pone.0115457
Publisher: Public Library of Science
Keywords: (Prop-2-ynyloxy)benzene; Propargyl bromide; Antiurease; Antibacterial
Depositing User: Nabilah Mustapa
Date Deposited: 31 Jul 2015 12:08
Last Modified: 24 Aug 2015 00:53
Altmetrics: http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.1371/journal.pone.0115457
URI: http://psasir.upm.edu.my/id/eprint/36149
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