Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system

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The rigid 6-oxobicyclo[3.1.0]hexane scaffold, characteristic of the natural antibiotic neplanocin C (3), was used to build prototypes of conformationally locked deoxynucleosides in the North hemisphere of the pseudorotational cycle. The purine analogues 6 and 7 are conformationally equivalent to car...

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Autores principales:	Comin, M.J., Rodriguez, J.B., Russ, P., Marquez, V.E.
Formato:	JOUR
Materias:	2′-deoxyneplanocin C 6-oxobicyclo[3.1.0]hexane Antiviral activity, EBV Carbocyclic nucleosides Conformationally locked nucleosides 2 amino 9 [4 hydroxy 5 (hydroxymethyl) 6 oxabicyclo[3.1.0]hex 2 yl]hydropurin 6 one 4 (6 aminopurin 9 yl) 1 (hydroxymethyl) 6 oxabicyclo[3.1.0]hexan 2 ol 8 hydroxy 7 (phenylmethoxy) 8 [(phenylmethoxy)methyl] 5,6,7,8,5a,8a hexahydro 5ah,8ah cyclopenta[1,2 d]pyrimidino[2,1 b] 1,3 oxazolidin 2 one antibiotic agent bicyclo compound carbocyclic nucleoside deoxyguanosine derivative heterocyclic compound neplanocin c oxabicyclo[3.1.0]hexane purine derivative unclassified drug antiviral activity article drug conformation drug synthesis Epstein Barr virus Mitsunobu reaction priority journal rotation
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_00404020_v59_n3_p295_Comin
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	todo:paper_00404020_v59_n3_p295_Comin2023-10-03T14:50:41Z Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system Comin, M.J. Rodriguez, J.B. Russ, P. Marquez, V.E. 2′-deoxyneplanocin C 6-oxobicyclo[3.1.0]hexane Antiviral activity, EBV Carbocyclic nucleosides Conformationally locked nucleosides 2 amino 9 [4 hydroxy 5 (hydroxymethyl) 6 oxabicyclo[3.1.0]hex 2 yl]hydropurin 6 one 4 (6 aminopurin 9 yl) 1 (hydroxymethyl) 6 oxabicyclo[3.1.0]hexan 2 ol 8 hydroxy 7 (phenylmethoxy) 8 [(phenylmethoxy)methyl] 5,6,7,8,5a,8a hexahydro 5ah,8ah cyclopenta[1,2 d]pyrimidino[2,1 b] 1,3 oxazolidin 2 one antibiotic agent bicyclo compound carbocyclic nucleoside deoxyguanosine derivative heterocyclic compound neplanocin c oxabicyclo[3.1.0]hexane purine derivative unclassified drug antiviral activity article drug conformation drug synthesis Epstein Barr virus Mitsunobu reaction priority journal rotation The rigid 6-oxobicyclo[3.1.0]hexane scaffold, characteristic of the natural antibiotic neplanocin C (3), was used to build prototypes of conformationally locked deoxynucleosides in the North hemisphere of the pseudorotational cycle. The purine analogues 6 and 7 are conformationally equivalent to carbocyclic nucleosides built with the bicyclo[3.1.0]hexane template. The pyrimidine nucleosides were unstable and underwent a facile intramolecular epoxide ring-opening reaction leading to heterocycle 22. Only the deoxyguanosine analogue 7 showed antiviral activity against EBV. © 2003 Elsevier Science Ltd. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v59_n3_p295_Comin
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	2′-deoxyneplanocin C 6-oxobicyclo[3.1.0]hexane Antiviral activity, EBV Carbocyclic nucleosides Conformationally locked nucleosides 2 amino 9 [4 hydroxy 5 (hydroxymethyl) 6 oxabicyclo[3.1.0]hex 2 yl]hydropurin 6 one 4 (6 aminopurin 9 yl) 1 (hydroxymethyl) 6 oxabicyclo[3.1.0]hexan 2 ol 8 hydroxy 7 (phenylmethoxy) 8 [(phenylmethoxy)methyl] 5,6,7,8,5a,8a hexahydro 5ah,8ah cyclopenta[1,2 d]pyrimidino[2,1 b] 1,3 oxazolidin 2 one antibiotic agent bicyclo compound carbocyclic nucleoside deoxyguanosine derivative heterocyclic compound neplanocin c oxabicyclo[3.1.0]hexane purine derivative unclassified drug antiviral activity article drug conformation drug synthesis Epstein Barr virus Mitsunobu reaction priority journal rotation
spellingShingle	2′-deoxyneplanocin C 6-oxobicyclo[3.1.0]hexane Antiviral activity, EBV Carbocyclic nucleosides Conformationally locked nucleosides 2 amino 9 [4 hydroxy 5 (hydroxymethyl) 6 oxabicyclo[3.1.0]hex 2 yl]hydropurin 6 one 4 (6 aminopurin 9 yl) 1 (hydroxymethyl) 6 oxabicyclo[3.1.0]hexan 2 ol 8 hydroxy 7 (phenylmethoxy) 8 [(phenylmethoxy)methyl] 5,6,7,8,5a,8a hexahydro 5ah,8ah cyclopenta[1,2 d]pyrimidino[2,1 b] 1,3 oxazolidin 2 one antibiotic agent bicyclo compound carbocyclic nucleoside deoxyguanosine derivative heterocyclic compound neplanocin c oxabicyclo[3.1.0]hexane purine derivative unclassified drug antiviral activity article drug conformation drug synthesis Epstein Barr virus Mitsunobu reaction priority journal rotation Comin, M.J. Rodriguez, J.B. Russ, P. Marquez, V.E. Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
topic_facet	2′-deoxyneplanocin C 6-oxobicyclo[3.1.0]hexane Antiviral activity, EBV Carbocyclic nucleosides Conformationally locked nucleosides 2 amino 9 [4 hydroxy 5 (hydroxymethyl) 6 oxabicyclo[3.1.0]hex 2 yl]hydropurin 6 one 4 (6 aminopurin 9 yl) 1 (hydroxymethyl) 6 oxabicyclo[3.1.0]hexan 2 ol 8 hydroxy 7 (phenylmethoxy) 8 [(phenylmethoxy)methyl] 5,6,7,8,5a,8a hexahydro 5ah,8ah cyclopenta[1,2 d]pyrimidino[2,1 b] 1,3 oxazolidin 2 one antibiotic agent bicyclo compound carbocyclic nucleoside deoxyguanosine derivative heterocyclic compound neplanocin c oxabicyclo[3.1.0]hexane purine derivative unclassified drug antiviral activity article drug conformation drug synthesis Epstein Barr virus Mitsunobu reaction priority journal rotation
description	The rigid 6-oxobicyclo[3.1.0]hexane scaffold, characteristic of the natural antibiotic neplanocin C (3), was used to build prototypes of conformationally locked deoxynucleosides in the North hemisphere of the pseudorotational cycle. The purine analogues 6 and 7 are conformationally equivalent to carbocyclic nucleosides built with the bicyclo[3.1.0]hexane template. The pyrimidine nucleosides were unstable and underwent a facile intramolecular epoxide ring-opening reaction leading to heterocycle 22. Only the deoxyguanosine analogue 7 showed antiviral activity against EBV. © 2003 Elsevier Science Ltd. All rights reserved.
format	JOUR
author	Comin, M.J. Rodriguez, J.B. Russ, P. Marquez, V.E.
author_facet	Comin, M.J. Rodriguez, J.B. Russ, P. Marquez, V.E.
author_sort	Comin, M.J.
title	Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_short	Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_full	Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_fullStr	Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_full_unstemmed	Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_sort	synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
url	http://hdl.handle.net/20.500.12110/paper_00404020_v59_n3_p295_Comin
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_version_	1807321471797690368

Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system

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