UMYMFOR 05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
artículos
Título:
Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agen
Autor/es:
ELHALEM, ELEONORA; PUJOL, CARLOS A.; DAMONTE, ELSA B.; RODRIGUEZ, JUAN BAUTISTA
Revista:
TETRAHEDRON
Editorial:
PERGAMON-ELSEVIER SCIENCE LTD
Referencias:
Año: 2010 p. 3332 - 3340
ISSN:
0040-4020
Resumen:
As a continuation of our project aimed at the search for new antiviral agents, the synthesis and biological evaluation of N-thia-carba-thymidine ((1R,2S,4S,5S)-5-methyl-1-{6-thia-4-hydroxy-5-[(hydroxy)-methyl]bicyclo[3.1.0]hex-2-yl}-1,3-dihydropyrimidine-2,4-dione; compound 8) was carried out employing the carbocyclic enantioenriched intermediate (1R,4S)-4-phenylmethoxy-3-[(phenylmethoxy)methyl]cyclopent-2-en-1-ol, which in turn was prepared from (3R,4S) phenylmethoxy-3-[(phenylmethoxy)methyl]-cyclopent-1-ene. The title compound resulted to be a very potent antiherpetic agent exhibiting a similar potency to acyclovir as shown. The synthetic approach to obtain this carbanucleoside required a novel strategy to introduce a thiirane group fused to a functionalized five-membered ring.
