Meier et al., 1999 - Google Patents

cyclo Sal-Pronucleotides of 2 '-Fluoro-ara-and 2 '-Fluoro-ribo-2 ', 3 '-dideoxyadenosine as a Strategy to Bypass a Metabolic Blockade

Meier et al., 1999

Document ID
16135130339180139798
Author
Meier C
Knispel T
Marquez V
Siddiqui M
De Clercq E
Balzarini J
Publication year
Publication venue
Journal of medicinal chemistry

External Links

Snippet

Novel, lipophilic cyclo Sal triesters 4a− c and 5a− c were synthesized, respectively, from the ara-and ribo-configurated 2 '-fluorinated-2 ', 3 '-dideoxyadenosines 2 and 3. The cyclo Sal phosphotriesters were used as tools to study the effects of the two different sugar pucker …
Continue reading at pubs.acs.org (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES OR MICRO-ORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or micro-organisms; Compositions therefor; Processes of preparing such compositions

Similar Documents

Publication Publication Date Title
Meier et al. cyclo Sal-Pronucleotides of 2 ‘-Fluoro-ara-and 2 ‘-Fluoro-ribo-2 ‘, 3 ‘-dideoxyadenosine as a Strategy to Bypass a Metabolic Blockade
Meier et al. cyclo Sal-Pronucleotides of 2 ‘, 3 ‘-Dideoxyadenosine and 2 ‘, 3 ‘-Dideoxy-2 ‘, 3 ‘-didehydroadenosine: Synthesis and Antiviral Evaluation of a Highly Efficient Nucleotide Delivery System
Meier et al. cyclo Sal-2 ‘, 3 ‘-dideoxy-2 ‘, 3 ‘-didehydrothymidine Monophosphate (cyclo Sal-d4TMP): Synthesis and Antiviral Evaluation of a New d4TMP Delivery System
Thornton et al. Nucleoside phosphate and phosphonate prodrug clinical candidates: Miniperspective
Eldrup et al. structure− activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase
McGuigan et al. Aryl phosphoramidate derivatives of d4T have improved anti-HIV efficacy in tissue culture and may act by the generation of a novel intracellular metabolite
Marquez et al. HIV-1 reverse transcriptase can discriminate between two conformationally locked carbocyclic AZT triphosphate analogues
McIntee et al. Probing the mechanism of action and decomposition of amino acid phosphomonoester amidates of antiviral nucleoside prodrugs
McGuigan et al. Application of phosphoramidate pronucleotide technology to abacavir leads to a significant enhancement of antiviral potency
KR101774429B1 (en) Purine nucleoside monophosphate prodrugs for treatment of cancer and viral infections
Abraham et al. Synthesis and biological activity of aromatic amino acid phosphoramidates of 5-fluoro-2 ‘-deoxyuridine and 1-β-arabinofuranosylcytosine: evidence of phosphoramidase activity
Chou et al. Phosphoramidate pronucleotides: a comparison of the phosphoramidase substrate specificity of human and Escherichia coli histidine triad nucleotide binding proteins
Murakami et al. Adenosine deaminase-like protein 1 (ADAL1): characterization and substrate specificity in the hydrolysis of N6-or O6-substituted purine or 2-aminopurine nucleoside monophosphates
Chang et al. Amino acid phosphoramidate monoesters of 3 ‘-azido-3 ‘-deoxythymidine: Relationship between antiviral potency and intracellular metabolism
WO2003062256A1 (en) 2'-beta-modified-6-substituted adenosine analogs and their use as antiviral agents
Choi et al. Structure− activity relationships of (e)-5-(2-bromovinyl) uracil and related pyrimidine nucleosides as antiviral agents for herpes viruses
Meier et al. cyclo Sal-PMEA and c yclo Amb-PMEA: Potentially New Phosphonate Prodrugs Based on the cyclo Sal-Pronucleotide Approach
Wnuk et al. Anticancer and antiviral effects and inactivation of S-adenosyl-l-homocysteine hydrolase with 5 ‘-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues
Okon et al. Anchimerically activatable antiviral protides
Meier et al. C yclo Sal-BVDUMP Pronucleotides: How to Convert an Antiviral-Inactive Nucleoside Analogue into a Bioactive Compound against EBV
Khandazhinskaya et al. Carbocyclic dinucleoside polyphosphonates: Interaction with HIV reverse transcriptase and antiviral activity
Bondada et al. Adenosine dioxolane nucleoside phosphoramidates as antiviral agents for human immunodeficiency and hepatitis B viruses
Prakash et al. Synthesis and Evaluation of S-Acyl-2-thioethyl Esters of Modified Nucleoside 5 ‘-Monophosphates as Inhibitors of Hepatitis C Virus RNA Replication
Zhou et al. Synthesis and evaluation of 2, 6-modified purine 2′-C-methyl ribonucleosides as inhibitors of HCV replication
Choo et al. Synthesis and anti-HIV activity of D-and L-thietanose nucleosides