Marchand et al., 1999 - Google Patents

Stereospecific synthesis of unnatural β-L-enantiomers of 2-chloroadenine pentofuranonucleoside derivatives

Marchand et al., 1999

Document ID
18146831360055687627
Author
Marchand A
Lioux T
Mathé C
Imbach J
Gosselin G
Publication year
Publication venue
Journal of the Chemical Society, Perkin Transactions 1

External Links

Snippet

2′, 3′-Dideoxy-(1), 2′, 3′-unsaturated-(2), 2′, 3′-dideoxy-3′-fluoro-(3), 3′-azido- 2′, 3′-dideoxy-(4) and 2′-deoxy-(5) β-L-ribofuranonucleosides of 2-chloroadenine have been synthesised and their antiviral properties examined. All these derivatives were …
Continue reading at pubs.rsc.org (other versions)

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16Purine radicals
    • C07H19/20Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • C07H19/10Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16Purine radicals
    • C07H19/167Purine radicals with ribosyl as the saccharide radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/052Imidazole radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D473/00Heterocyclic compounds containing purine ring systems
    • C07D473/26Heterocyclic compounds containing purine ring systems with an oxygen, sulfur or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32Nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D473/00Heterocyclic compounds containing purine ring systems
    • C07D473/02Heterocyclic compounds containing purine ring systems with oxygen, sulfur or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/18Heterocyclic compounds containing purine ring systems with oxygen, sulfur or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D473/00Heterocyclic compounds containing purine ring systems
    • C07D473/40Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in positions 2 or 6
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/70Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02Monosaccharides

Similar Documents

Publication Publication Date Title
US5446139A (en) Purine analog nucleoside and nucleotide compounds
KR101195019B1 (en) Modified nucleosides for treatment of viral infections and abnormal cellular proliferation
US6525191B1 (en) Conformationally constrained L-nucleosides
AU784374C (en) Synthesis of 2'-deoxy-L-nucleosides
WO2008143846A1 (en) Azido purine nucleosides for treatment of viral infections
HU199871B (en) Process for producing deazapurine nucleoside derivatives and antiviral compositions comprising said compounds
KR20030061792A (en) Nucleoside derivatives
WO2010068708A2 (en) 3'-azido purine nucleotide prodrugs for treatment of viral infections
NO171507B (en) ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE NUCLEOTIDE DERIVATIVES
GB2372742A (en) C2,5'-Disubstituted and N6,C2,5'-trisubstituted adenosine derivatives and their different uses
Gosselin et al. Synthesis and antiviral evaluation of β‐L‐Xylo‐fuanosyl nucleosides of the five naturally occurring nucleic acid bases
EP0720604B1 (en) Conformationally locked nucleoside analogues
Ford Jr et al. Lipophilic, Acid-Stable, Adenosine Deaminase-Activated Anti-HIV Prodrugs for Central Nervous System Delivery. 2. 6-Halo-and 6-Alkoxy Prodrugs of 2'-. beta.-Fluoro-2', 3'-dideoxyinosine
NO173996B (en) ANALOGUE PROCEDURE FOR THE PREPARATION OF SELECTIVE ADENOSIN RECEPTOR AGENTS
Marchand et al. Stereospecific synthesis of unnatural β-L-enantiomers of 2-chloroadenine pentofuranonucleoside derivatives
Matušková et al. From synthesis to the biological effect of isoprenoid 2′-deoxyriboside and 2′, 3′-dideoxyriboside cytokinin analogues
WO1997033591A1 (en) A method of treating disorders related to cytokines in mammals
Jeannot et al. Synthesis and studies of 3′-C-trifluoromethyl nucleoside analogues bearing adenine or cytosine as the base
Griffon et al. Stereospecific synthesis and biological evaluations of β-L-pentofuranonucleoside derivatives of 5-fluorouracil and 5-fluorocytosine
Van Rompaey et al. Exploring human adenosine A3 receptor complementarity and activity for adenosine analogues modified in the ribose and purine moiety
Cosyn et al. Synthesis of hypermodified adenosine derivatives as selective adenosine A3 receptor ligands
Marchand et al. Synthesis and Antiviral Evaluation of Unnatural β-L-Enantiomers of 3′-Fluoro-and 3′-Azido-2, 3′-dideoxyguanosine Derivatives
Zhang et al. Synthesis and evaluation of 3′-azido-2′, 3′-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus
Kim et al. Design, synthesis, and biological evaluation of novel iso-d-2′, 3′-dideoxy-3′-fluorothianucleoside derivatives
Ciurea et al. Synthesis of 5-alkynylated d4T analogues as potential HIV-1 reverse transcriptase inhibitors