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Abstract:

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. © 2010 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent
Autor:Elhalem, E.; Pujol, C.A.; Damonte, E.B.; Rodriguez, J.B.
Filiación:Departamento de Química Orgánica and UMYMFOR (CONICET-FCEyN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina
Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Pabellon 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina
Palabras clave:4 phenylmethoxy 3 [(phenylmethoxy)methyl]cyclopent 2 en ol; 5 methyl 1 [4 (benzyloxy) 5 [(benzyloxy)methyl] 6 thiabicyclo[3.1.0]hex 2 yl] 3 benzoyl 1,3 dihydropyrimidine 2,4 dione; 5 methyl 1 [4 hydroxy 5 [(hydroxy)methyl] 6 thiabicyclo[3.1.0]hex 2 yl] 1,3 dihydropyrimidine 2,4 dione; aciclovir; alkane derivative; antivirus agent; benzyl derivative; bicyclo compound; cyclopentene derivative; phenylmethoxy 3 [(phenylmethoxy)methyl]cyclopent 1 ene; pyrimidine derivative; thiabicyclo[3.1.0]hexane derivative; unclassified drug; animal cell; antiviral activity; article; controlled study; drug mechanism; drug screening; drug synthesis; herpes simplex; Herpes simplex virus 1; Herpes simplex virus 2; IC 50; nonhuman; priority journal; structure activity relation; Thia
Año:2010
Volumen:66
Número:18
Página de inicio:3332
Página de fin:3340
DOI: http://dx.doi.org/10.1016/j.tet.2010.02.092
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
CAS:aciclovir, 59277-89-3
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v66_n18_p3332_Elhalem

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Citas:

---------- APA ----------
Elhalem, E., Pujol, C.A., Damonte, E.B. & Rodriguez, J.B. (2010) . Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent. Tetrahedron, 66(18), 3332-3340.
http://dx.doi.org/10.1016/j.tet.2010.02.092
---------- CHICAGO ----------
Elhalem, E., Pujol, C.A., Damonte, E.B., Rodriguez, J.B. "Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent" . Tetrahedron 66, no. 18 (2010) : 3332-3340.
http://dx.doi.org/10.1016/j.tet.2010.02.092
---------- MLA ----------
Elhalem, E., Pujol, C.A., Damonte, E.B., Rodriguez, J.B. "Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent" . Tetrahedron, vol. 66, no. 18, 2010, pp. 3332-3340.
http://dx.doi.org/10.1016/j.tet.2010.02.092
---------- VANCOUVER ----------
Elhalem, E., Pujol, C.A., Damonte, E.B., Rodriguez, J.B. Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent. Tetrahedron. 2010;66(18):3332-3340.
http://dx.doi.org/10.1016/j.tet.2010.02.092