Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Regular Articles
Improved Microwave-Mediated Synthesis of 3-(3-Aryl-1,2,4-oxadiazol-5-yl)propionic Acids and Their Larvicidal and Fungal Growth Inhibitory Properties
Ricardo Antonio Wanderley Neves FilhoCecília Aguiar da SilvaClécia Sipriano Borges da SilvaVanessa Passos BrusteinDaniela Maria do Amaral Ferraz NavarroFábio André Brayner dos SantosLuiz Carlos AlvesMarília Gabriela dos Santos CavalcantiRajendra Mohan SrivastavaMaria das Graças Carneiro-Da-Cunha
Author information
JOURNAL FREE ACCESS

2009 Volume 57 Issue 8 Pages 819-825

Details
Abstract

The synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids from arylamidoximes and succinic anhydride under focused microwave irradiation conditions is described. The new synthetic method furnished the desired products in 2—3 min and good yields. Furthermore, the previously complicated purification procedure has been simplified in a manner which is quick, eco-friendly and cost-effective. Larvicidal bioassay and fungal growth inhibitory tests were performed using several 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids. These acids presented strong larvicidal activity against L4 larvae of Aedes aegypti. The results suggest that larvicidal activity might be correlated with the presence of electron-withdrawing substituents in the para position of the phenyl ring except the fluorine atom. The alterations observed in the larvae spiracular valves of the siphon and anal papillae by 1,2,4-oxadiazoles in the larvicidal bioassay are responsible for larvae's death. Furthermore, all acids inhibited the fungal growth of five different types of fungi, viz., Fusarium solani, F. oxysporum, F. moniliforme, F. decemcellulare and F. lateritium in a preliminary evaluation. Both of these activities are being disclosed for the first time for 1,2,4-oxadiazole-5-yl ring linked at C-3 of propionic acid.

Content from these authors
© 2009 The Pharmaceutical Society of Japan
Previous article Next article
feedback
Top