Antiinflammatory property of 3-aryl-5-(n-propyl)-1,2,4-oxadiazoles and antimicrobial property of 3-aryl-5-(n-propyl)-4,5-dihydro-1,2,4-oxadiazoles: their syntheses and spectroscopic studies.
The synthesis of six 3-aryl-5-(n-propyl)-4,5dihydro-1,2,4-oxadiazoles 3a-f has been achieved in a facile manner by the reaction of an appropriate arylamidoxime 1a-f with butyraldehyde 2. Oxidation of 3a-f individually using MnO(2) in CH(2)Cl(2) or sodium hypochlorite in THF/H(2)O furnished 1,2,4-oxadiazoles 4a-f in good to excellent yields. Compounds 4a-f were also evaluated against inflammation. Except 4e, all of them reduced inflammation, however, 4c presented better antiinflammatory activity. A preliminary antimicrobial activity tests of 3a-f showed that these compounds possess activity against some microorganisms. In fact, 3c and 3f have been found to be more effective against Staphylococcus aureus, Mycobacterium smegmatis, and Candida albicans.
Srivastava
Rajendra M
RM
Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, 50.740-540 Recife, PE, Brazil. rmns@npd.ufpe.br
de Almeida Lima
Analice
A
Viana
Osnir S
OS
da Costa Silva
Marcelo J
MJ
Catanho
Maria T J A
MT
de Morais
José Otamar F
JO
D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D001241:Aspirin / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D004487:Edema / Q000188:drug therapy; D021902:Enterobacter aerogenes / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D051379:Mice; D008826:Microbial Sensitivity Tests; D020102:Mycobacterium smegmatis / Q000187:drug effects; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013057:Spectrum Analysis / Q000379:methods; D013211:Staphylococcus aureus / Q000187:drug effects
D000890:Anti-Infective Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D010069:Oxadiazoles; D001241:Aspirin