Synthesis and antiallergenic properties of 3-n-pentadecyl- and 3-n-heptadecylcatechol esters.
J Pharm Sci
; 72(7): 792-5, 1983 Jul.
Article
em En
| MEDLINE
| ID: mdl-6224926
ABSTRACT
A synthetic procedure is described for the preparation of 3-n-pentadecyl- and 3-n-heptadecylcatechols and their acetate and alaninate esters. The Wittig reagent prepared from 2,3-dimethoxybenzyltriphenylphosphonium bromide (III) was coupled with 1-tetradecanal or 1-hexadecanal to give the olefins IV and V, respectively. Catalytic reduction of IV and V followed by demethylation with boron tribromide afforded VIII and IX. The acetates were prepared using acetic anhydride and pyridine, while the alaninates were prepared using N-(tert-butoxycarbonyl)-L-alanine and dicyclohexylcarbodiimide followed by removal of the tert-butoxycarbonyl group with hydrogen chloride gas. The esters were active in guinea pigs in the production of tolerance and desensitization or hyposensitization to poison ivy-type contact dermatitis.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Catecóis
/
Dermatite por Toxicodendron
Limite:
Animals
Idioma:
En
Revista:
J Pharm Sci
Ano de publicação:
1983
Tipo de documento:
Article