BIOMAT Database Logo BIOMAT Database Logo

Synthesis and antiviral evaluation of α-D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides. 2010

Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Biochemicals Division, Yamasa Corporation, Choshi, Chiba, Japan. k_yamada@yamasa.com

We have identified a selective S(N)2' reaction triggered by iodide ion that leads to the ring-opening of 2,2'-anhydro-α-nucleosides. By applying the method, we have synthesized α-D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides, designed as potential antiviral agents.

UI MeSH Term Description Entries
D009705 Nucleosides Purine or pyrimidine bases attached to a ribose or deoxyribose. (From King & Stansfield, A Dictionary of Genetics, 4th ed) Nucleoside,Nucleoside Analog,Nucleoside Analogs,Analog, Nucleoside,Analogs, Nucleoside
D003587 Cytomegalovirus A genus of the family HERPESVIRIDAE, subfamily BETAHERPESVIRINAE, infecting the salivary glands, liver, spleen, lungs, eyes, and other organs, in which they produce characteristically enlarged cells with intranuclear inclusions. Infection with Cytomegalovirus is also seen as an opportunistic infection in AIDS. Herpesvirus 5, Human,Human Herpesvirus 5,Salivary Gland Viruses,HHV 5,Herpesvirus 5 (beta), Human,Cytomegaloviruses,Salivary Gland Virus,Virus, Salivary Gland,Viruses, Salivary Gland
D006678 HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2. AIDS Virus,HTLV-III,Human Immunodeficiency Viruses,Human T-Cell Lymphotropic Virus Type III,Human T-Lymphotropic Virus Type III,LAV-HTLV-III,Lymphadenopathy-Associated Virus,Acquired Immune Deficiency Syndrome Virus,Acquired Immunodeficiency Syndrome Virus,Human Immunodeficiency Virus,Human T Cell Lymphotropic Virus Type III,Human T Lymphotropic Virus Type III,Human T-Cell Leukemia Virus Type III,Immunodeficiency Virus, Human,Immunodeficiency Viruses, Human,Virus, Human Immunodeficiency,Viruses, Human Immunodeficiency,AIDS Viruses,Human T Cell Leukemia Virus Type III,Lymphadenopathy Associated Virus,Lymphadenopathy-Associated Viruses,Virus, AIDS,Virus, Lymphadenopathy-Associated,Viruses, AIDS,Viruses, Lymphadenopathy-Associated
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000998 Antiviral Agents Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. Antiviral,Antiviral Agent,Antiviral Drug,Antivirals,Antiviral Drugs,Agent, Antiviral,Agents, Antiviral,Drug, Antiviral,Drugs, Antiviral
D014777 Virus Diseases A general term for diseases caused by viruses. Viral Diseases,Viral Infections,Virus Infections,Disease, Viral,Disease, Virus,Diseases, Viral,Diseases, Virus,Infection, Viral,Infection, Virus,Infections, Viral,Infections, Virus,Viral Disease,Viral Infection,Virus Disease,Virus Infection
D014780 Viruses Minute infectious agents whose genomes are composed of DNA or RNA, but not both. They are characterized by a lack of independent metabolism and the inability to replicate outside living host cells. Animal Viruses,Zoophaginae,Animal Virus,Virus,Virus, Animal,Viruses, Animal
D018139 Simplexvirus A genus of the family HERPESVIRIDAE, subfamily ALPHAHERPESVIRINAE, consisting of herpes simplex-like viruses. The type species is HERPESVIRUS 1, HUMAN. Herpes Simplex Virus,Herpesvirus 1, Saimiriine,Herpesvirus 1, Saimirine,Herpesvirus 16, Cercopithecine,Marmoset Virus,Cercopithecine Herpesvirus 16,Herpes Labialis Virus,Herpes-T Virus,Herpesvirus 1 (alpha), Saimirine,Herpesvirus Hominis,Herpesvirus Papio 2,Herpesvirus Platyrhinae,Marmoset Herpesvirus,Saimiriine Herpesvirus 1,Herpes Labialis Viruses,Herpes Simplex Viruses,Herpes T Virus,Herpes-T Viruses,Herpesvirus Homini,Herpesvirus, Marmoset,Herpesviruses, Marmoset,Homini, Herpesvirus,Hominis, Herpesvirus,Labialis Virus, Herpes,Labialis Viruses, Herpes,Marmoset Herpesviruses,Marmoset Viruses,Platyrhinae, Herpesvirus,Saimirine Herpesvirus 1,Simplexviruses,Virus, Herpes Labialis,Viruses, Herpes Labialis

Related Publications

Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Synthesis and antiviral evaluation of 2',3'-dideoxy-2'-fluoro-3'- C-hydroxymethyl-beta-D-arabinofuranosyl pyrimidine nucleosides.
January 2003, Nucleosides, nucleotides & nucleic acids,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
3'-Carbon-substituted pyrimidine nucleosides having a 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy structure: synthesis and antiviral evaluation.
January 2006, Antiviral chemistry & chemotherapy,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Asymmetric synthesis and antiviral activities of L-carbocyclic 2', 3'-didehydro-2',3'-dideoxy and 2',3'-dideoxy nucleosides.
August 1999, Journal of medicinal chemistry,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Synthesis of 2',3'-dideoxy-3'-C-(hydroxymethyl)-4'-thiopentofuranosyl nucleosides as potential antiviral agent.
April 1999, Bioorganic & medicinal chemistry letters,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Nucleosides. XVI. The synthesis of 2',3'-dideoxy-3',4'-didehydro nucleosides.
March 1973, The Journal of organic chemistry,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Synthesis, antiviral activity, and mechanism of drug resistance of D- and L-2',3'-didehydro-2',3'-dideoxy-2'-fluorocarbocyclic nucleosides.
June 2005, Journal of medicinal chemistry,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Synthesis and antiviral evaluation of thieno[3,4-d]pyrimidine C-nucleoside analogues of 2',3'-dideoxy- and 2',3'-dideoxy-2',3'-didehydro-adenosine and -inosine.
March 2009, Bioorganic & medicinal chemistry,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Synthesis and HIV inhibition activity of 2',3'-dideoxy-3'-C-hydroxymethyl nucleosides.
December 1996, Journal of medicinal chemistry,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Synthesis of 3'-fluoro-2',3'-dideoxy-2',3'-didehydro-4'-ethynyl-D- and -L-furanosyl nucleosides.
September 2004, The Journal of organic chemistry,
Kohei Yamada, and Hiroyuki Hayakawa, and Shinji Sakata, and Noriyuki Ashida, and Yuichi Yoshimura
Stereoselective synthesis of beta-L-2',3'-dideoxy- and L-2',3'-didehydro-2',3'-dideoxy purine nucleosides.
January 1999, Nucleosides & nucleotides,
Copied contents to your clipboard!