Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent

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 employ...

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Autores principales:	Elhalem, Eleonora, Pujol, Carlos Alberto, Damonte, Elsa Beatriz, Rodríguez, Juan Bautista
Publicado:	2010
Materias:	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
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v66_n18_p3332_Elhalem http://hdl.handle.net/20.500.12110/paper_00404020_v66_n18_p3332_Elhalem
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	paper:paper_00404020_v66_n18_p3332_Elhalem2023-06-08T15:04:19Z Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent Elhalem, Eleonora Pujol, Carlos Alberto Damonte, Elsa Beatriz Rodríguez, Juan Bautista 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 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. Fil:Elhalem, E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Pujol, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Damonte, E.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Rodriguez, J.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2010 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v66_n18_p3332_Elhalem http://hdl.handle.net/20.500.12110/paper_00404020_v66_n18_p3332_Elhalem
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Elhalem, Eleonora Pujol, Carlos Alberto Damonte, Elsa Beatriz Rodríguez, Juan Bautista Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent
topic_facet	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
description	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.
author	Elhalem, Eleonora Pujol, Carlos Alberto Damonte, Elsa Beatriz Rodríguez, Juan Bautista
author_facet	Elhalem, Eleonora Pujol, Carlos Alberto Damonte, Elsa Beatriz Rodríguez, Juan Bautista
author_sort	Elhalem, Eleonora
title	Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent
title_short	Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent
title_full	Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent
title_fullStr	Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent
title_full_unstemmed	Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent
title_sort	synthesis and biological evaluation of n-thia-carba-thymidine as an antiherpetic agent
publishDate	2010
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v66_n18_p3332_Elhalem http://hdl.handle.net/20.500.12110/paper_00404020_v66_n18_p3332_Elhalem
work_keys_str_mv	AT elhalemeleonora synthesisandbiologicalevaluationofnthiacarbathymidineasanantiherpeticagent AT pujolcarlosalberto synthesisandbiologicalevaluationofnthiacarbathymidineasanantiherpeticagent AT damonteelsabeatriz synthesisandbiologicalevaluationofnthiacarbathymidineasanantiherpeticagent AT rodriguezjuanbautista synthesisandbiologicalevaluationofnthiacarbathymidineasanantiherpeticagent
_version_	1768546152265809920

Synthesis and biological evaluation of N-thia-carba-thymidine as an antiherpetic agent

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