BIOMAT Database Logo BIOMAT Database Logo

Regio- and stereoselective synthesis of carbocyclic 2',3'-dideoxy-3'-fluoro nucleosides as potential antiviral agents. 1994

T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Research Center, Asahi Glass Co., Ltd., Yokohama, Japan.

The synthesis and antiviral activity of racemic carbocyclic 2',3'-dideoxy-3'-fluoro nucleosides are reported. Carbocyclic 2',3'-dideoxy-3'-fluoro nucleosides were obtained from the 3-fluoro cyclopentane derivative 4, which was prepared by two methods. The SN2-displacement of the hydroxyl group of (+/-)-(1 beta, 2 alpha, 3 beta, 4 beta)-4-acetamido-2-fluoro-3-hydroxycyclopentylmethyl acetate (1) with Ph3P-I2 followed by tin hydride reduction afforded the 3-fluoroamino alcohol derivative 3. Alternatively, the protected fluoroamino alcohol 3 was prepared by regio- and stereoselective bromo-fluorination of cis-4 beta-acetamidocyclopent-2-enemethyl acetate (5) with hydrogen fluoride-pyridine/N-bromosuccinimide followed by tin hydride reduction to remove the bromine atom. Carbocyclic 2',3'-dideoxy-3'-fluoroguanosine (14) thus obtained was moderately active against herpes simplex virus in vitro.

UI MeSH Term Description Entries
D009980 Influenza A virus The type species of the genus ALPHAINFLUENZAVIRUS that causes influenza and other diseases in humans and animals. Antigenic variation occurs frequently between strains, allowing classification into subtypes and variants. Transmission is usually by aerosol (human and most non-aquatic hosts) or waterborne (ducks). Infected birds shed the virus in their saliva, nasal secretions, and feces. Alphainfluenzavirus influenzae,Avian Orthomyxovirus Type A,FLUAV,Fowl Plague Virus,Human Influenza A Virus,Influenza Virus Type A,Influenza Viruses Type A,Myxovirus influenzae-A hominis,Myxovirus influenzae-A suis,Myxovirus pestis galli,Orthomyxovirus Type A,Orthomyxovirus Type A, Avian,Orthomyxovirus Type A, Human,Orthomyxovirus Type A, Porcine,Pestis galli Myxovirus,Fowl Plague Viruses,Influenza A viruses,Myxovirus influenzae A hominis,Myxovirus influenzae A suis,Myxovirus, Pestis galli,Myxoviruses, Pestis galli,Pestis galli Myxoviruses,Plague Virus, Fowl,Virus, Fowl Plague
D002478 Cells, Cultured Cells propagated in vitro in special media conducive to their growth. Cultured cells are used to study developmental, morphologic, metabolic, physiologic, and genetic processes, among others. Cultured Cells,Cell, Cultured,Cultured Cell
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
D005461 Fluorine A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries. Fluorine-19,Fluorine 19
D006367 HeLa Cells The first continuously cultured human malignant CELL LINE, derived from the cervical carcinoma of Henrietta Lacks. These cells are used for, among other things, VIRUS CULTIVATION and PRECLINICAL DRUG EVALUATION assays. Cell, HeLa,Cells, HeLa,HeLa Cell
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000256 Adenoviridae A family of non-enveloped viruses infecting mammals (MASTADENOVIRUS) and birds (AVIADENOVIRUS) or both (ATADENOVIRUS). Infections may be asymptomatic or result in a variety of diseases. Adenoviruses,Ichtadenovirus,Adenovirus,Ichtadenoviruses
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014645 Herpesvirus 3, Human The type species of VARICELLOVIRUS causing CHICKENPOX (varicella) and HERPES ZOSTER (shingles) in humans. Chickenpox Virus,Herpes zoster Virus,Ocular Herpes zoster Virus,VZ Virus,Varicella-Zoster Virus,HHV-3,Herpesvirus 3 (alpha), Human,Herpesvirus Varicellae,Human Herpesvirus 3,Chickenpox Viruses,Herpes zoster Viruses,VZ Viruses,Varicella Zoster Virus,Varicella-Zoster Viruses,Varicellae, Herpesvirus

Related Publications

T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Synthesis of 2',3'-dideoxy-2'-fluoro-L-threo-pentofuranosyl nucleosides as potential antiviral agents.
October 1999, Nucleosides & nucleotides,
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Synthesis of carbocyclic nucleosides as potential antiviral agents.
January 2001, Nucleic acids research. Supplement (2001),
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
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,
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Stereoselective synthesis of novel thioiso dideoxy nucleosides with exocyclic methylene as potential antiviral agents.
January 2005, Nucleosides, nucleotides & nucleic acids,
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Synthesis of 2',3'-dideoxy-3'-fluoro-L-ribonucleosides as potential antiviral agents from D-sorbitol.
August 2000, Carbohydrate research,
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Synthesis and antiviral activities of novel 2', 4'- or 3', 4'-doubly branched carbocyclic nucleosides as potential antiviral agents.
August 2004, Archiv der Pharmazie,
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Synthesis and biological evaluation of novel 2',3',4'-triply branched carbocyclic nucleosides as potential antiviral agents.
November 2004, Archiv der Pharmazie,
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Synthesis and antiviral evaluation of novel 3'- and 4'-doubly branched carbocyclic nucleosides as potential antiviral agents.
December 2003, Archives of pharmacal research,
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Stereoselective synthesis and antiviral activity of D-2',3'-didehydro-2',3'-dideoxy-2'-fluoro-4'-thionucleosides.
October 2002, Journal of medicinal chemistry,
T Nakayama, and Y Matsumura, and Y Morizawa, and A Yasuda, and K Uchida, and H Takase, and Y Murakami, and S Atarashi, and T Ikeuchi, and Y Osada
Synthesis of 2',3'-dideoxy-3'-C-(hydroxymethyl)-4'-thiopentofuranosyl nucleosides as potential antiviral agent.
April 1999, Bioorganic & medicinal chemistry letters,
Copied contents to your clipboard!