Synthesis of conformationally restricted 2',3'-exo-methylene carbocyclic nucleosides built on a bicyclo[3.1.0]hexane template.
A series of 2',3'-exo-methylene carbocyclic nucleosides was synthesized as potential antiviral agents. These compounds were built on a bicyclo[3.1.0]hexane template that exhibits a rigid pseudoboat conformation and is capable of maintaining an identical conformation in solid state and in solution. The structures of the synthesized compounds were elucidated by NMR and X-ray crystallography. All the compounds were tested as anti-HIV and anti-HSV agents. The chemically synthesized 5'-triphosphate analogue of 7 was evaluated directly as a reverse transcriptase inhibitor.
Bhushan
Rashmi Gupta
RG
Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA.
Vince
Robert
R
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002522:Chlorocebus aethiops; D018360:Crystallography, X-Ray; D015497:HIV-1 / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects; D014709:Vero Cells
D000998:Antiviral Agents; D001643:Bridged Bicyclo Compounds; D009705:Nucleosides; C046059:bicyclo(3.1.0)hexane