Synthesis of carbovir and abacavir from a carbocyclic precursor. 2006

Robert Vince, and Mei Hua
Center for Drug Design, University of Minnesota, Minneapolis, Minnesota, USA.

A facile method for the synthesis of a carbocyclic analog of 2',3'-didehydro-2',3'-dideoxy-2-amino-6-chloropurine is presented, starting from the versatile lactam, 2-azabicyclo[2.2.1]hept-5-en-3-one. The corresponding anti-HIV nucleoside analogs, carbovir and its derivative abacavir, are prepared directly from the 6-chloro intermediate in one-step reactions.

UI MeSH Term Description Entries
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D013058 Mass Spectrometry An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers. Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass
D015224 Dideoxynucleosides Nucleosides that have two hydroxy groups removed from the sugar moiety. The majority of these compounds have broad-spectrum antiretroviral activity due to their action as antimetabolites. The nucleosides are phosphorylated intracellularly to their 5'-triphosphates and act as chain-terminating inhibitors of viral reverse transcription. 2',3'-Dideoxynucleosides,Dideoxyribonucleosides,ddNus,2',3' Dideoxynucleosides
D018894 Reverse Transcriptase Inhibitors Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. Reverse Transcriptase Inhibitor,Inhibitors, Reverse Transcriptase,Inhibitor, Reverse Transcriptase,Transcriptase Inhibitor, Reverse

Related Publications

Robert Vince, and Mei Hua
March 2012, Organic & biomolecular chemistry,
Robert Vince, and Mei Hua
January 1991, Nucleic acids symposium series,
Robert Vince, and Mei Hua
September 2015, Bioorganic & medicinal chemistry letters,
Robert Vince, and Mei Hua
January 1990, Drug metabolism and disposition: the biological fate of chemicals,
Robert Vince, and Mei Hua
September 2001, Antiviral chemistry & chemotherapy,
Robert Vince, and Mei Hua
January 1990, Drug metabolism and disposition: the biological fate of chemicals,
Robert Vince, and Mei Hua
May 2002, AIDS (London, England),
Robert Vince, and Mei Hua
January 1992, Drug metabolism and disposition: the biological fate of chemicals,
Robert Vince, and Mei Hua
January 2014, Beilstein journal of organic chemistry,
Copied contents to your clipboard!