1,2,4-oxadiazÃis: sÃntese, desenvolvimento de novas metodologias sintÃticas e avaliaÃÃo da atividade antiinflamatÃria

AUTOR(ES)
DATA DE PUBLICAÇÃO

2007

RESUMO

This work describes the obtainment of many novel 3,5-disubstituted 1,2,4-oxadiazoles. First, the synthesis of ten previously unknown 3-aryl-5-tridecyl- and 3-aryl-5-heptadecyl-1,2,4- oxadiazoles 40a-g, 40h-j, starting from arylamidoximes 12a-g and tetradecanoic as well as heptadecanoic acids 38a and 38b is reported. Second, seven new 3-aryl-5-(cis-heptadec-13- ene)-1,2,4-oxadiazoles 43a-g derived from arylamidoximes (12a-f,h) and oleic acid (or oleolyl chloride) have been prepared employing conventional and microwave irradiation methodologies. Molecular orbital calculations of heterocycles 43a-g using semi-empirical and ab initio (HF/6-31G) methods gave interesting information regarding the geometry and molecular conformation of these molecules. Third, the reaction of arylamidoximes (12a,c-f,h) and propioloyl chloride (44) unexpectedly furnished bis-aryl-1,2,4-oxadiazoles (47a-g). The mechanism of formation of these compounds is suggested for the first time. Fourth, an unusual production of 3-aryl-5-methyl-1,2,4-oxadiazoles (64a-g from arylamidoximes (12af, h) and 2,3-butanedione (57) has also been unravelled in the present work. Next, new methodologies for the synthesis of 1,2,4-oxadiazoles using either mesyl chloride or ethyl chloroformate with acids (38d-j) and arylamidoximes (12a,d,h), in an one pot procedure, were described herein. All the above-mentioned syntheses gave good to excellent yields of oxadiazoles. Finally, antiinflamatory property of compounds 40b-d has been evaluated using the acute peritonitis procedure. All these oxadiazoles caused 40-52% inflammation reduction in mice.

ASSUNTO(S)

1,2,4-oxadiazoles, fatty acids, acyl chlorides, 2,3-butanedione, antiinflammatory activity quimica 1,2,4-oxadiazÃis acidos graxos cloretos de Ãcidos 2,3-butadiona atividade antiinflamatÃria

ACESSO AO ARTIGO

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