262372-04-3Relevant academic research and scientific papers
A straightforward stereoselective synthesis of D- and L-5-hydroxy-4-hydroxymethyl-2-cyclohexenylguanine
Wang,Morral,Hendrix,Herdewijn
, p. 8478 - 8482 (2007/10/03)
A novel and facile synthesis of 5-hydroxy-4-hydroxymethyl-2-cyclohexenylguanine 1 is described. The key steps involve a Diels-Alder reaction of ethyl (2E)-3-acetyloxy-2-propenoate 2 as dienophile with Danishefsky's diene 3 to build up the six-membered ring skeleton, a Fraser-Reid reductive rearrangement of the adduct using LiAlH4, and base-moiety introduction using a Mitsunobu reaction. Optically pure D- and L-1 were obtained via resolution of intermediate 7 with (R)-(-)-methylmandelic acid. The synthetic procedure toward racemic 1 consists of only five steps and has proven to be highly efficient toward the synthesis of cyclohexenyl nucleosides.
(D)- and (L)-cyclohexenyl-G, a new class of antiviral agents: Synthesis, conformational analysis, molecular modeling, and biological activity
Wang,Froeyen,Hendrix,Andrei,Snoeck,Lescrinier,De Clercq,Herdewijn
, p. 727 - 730 (2007/10/03)
(D)- and (L)-cyclohexeneyl-G were synthesized enantioselectively starting from (R)-carvone. Both show potent and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). Molecular modeling demonstrates that both isomers are bound in the active site o
The cyclohexene ring system as a furanose mimic: Synthesis and antiviral activity of both enantiomers of cyclohexenylguanine
Wang, Jing,Froeyen, Matheus,Hendrix, Chris,Andrei, Graciela,Snoeck, Robert,De Clercq, Erik,Herdewijn, Piet
, p. 736 - 745 (2007/10/03)
Both enantiomers of cyclohexenylguanine were synthesized in a stereospecific way starting from the same starting material: R-(-)-carvone. Both compounds showed potent and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). The binding of both cy
