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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
Autor:Comin, M.J.; Rodriguez, J.B.; Russ, P.; Marquez, V.E.
Filiación:Departamento de Quimica Organica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Laboratory of Medicinal Chemistry, Center for Cancer Research, Natl. Cancer Institute, 376 Boyles St, Frederick, MD 21702-1201, United States
Palabras clave: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
Año:2003
Volumen:59
Número:3
Página de inicio:295
Página de fin:301
DOI: http://dx.doi.org/10.1016/S0040-4020(02)01528-4
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v59_n3_p295_Comin

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Citas:

---------- APA ----------
Comin, M.J., Rodriguez, J.B., Russ, P. & Marquez, V.E. (2003) . Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system. Tetrahedron, 59(3), 295-301.
http://dx.doi.org/10.1016/S0040-4020(02)01528-4
---------- CHICAGO ----------
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" . Tetrahedron 59, no. 3 (2003) : 295-301.
http://dx.doi.org/10.1016/S0040-4020(02)01528-4
---------- MLA ----------
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" . Tetrahedron, vol. 59, no. 3, 2003, pp. 295-301.
http://dx.doi.org/10.1016/S0040-4020(02)01528-4
---------- VANCOUVER ----------
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. Tetrahedron. 2003;59(3):295-301.
http://dx.doi.org/10.1016/S0040-4020(02)01528-4