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60084-10-8,MFCD00866494
Catalog No.:AA00ECJ6

60084-10-8 | 2-b-D-Ribofuranosyl-4-thiazolecarboxamide

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00ECJ6
Chemical Name:
2-b-D-Ribofuranosyl-4-thiazolecarboxamide
CAS Number:
60084-10-8
Molecular Formula:
C9H12N2O5S
Molecular Weight:
260.2670
MDL Number:
MFCD00866494
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)c1scc(n1)C(=O)N
Properties
Computed Properties
 
Complexity:
305  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
3  
XLogP3:
-1.7  

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,1977,vol.20,p.256-262

[1]JournalofMedicinalChemistry,1977,vol.20,p.256-262

[1]Nucleosides,nucleotidesandnucleicacids,2004,vol.23,p.715-724

[2]JournalofMedicinalChemistry,1977,vol.20,p.256-262

[3]JournalofOrganicChemistry,1976,vol.41,p.4074-4077

[4]NucleosidesandNucleotides,1999,vol.18,p.2425-2431

[5]JournalofOrganicChemistry,1985,vol.50,p.1741-1746

[1]JournalofMedicinalChemistry,1983,vol.26,p.922-925

[2]JournalofOrganicChemistry,1976,vol.41,p.4074-4077

[1]TetrahedronLetters,1984,vol.25,p.2111-2114

Literature

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Title: Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside.

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Title: Synthesis of novel aza-analogues of tiazofurin with 2-[5,5-bis(hydroxymethyl)pyrrolidin-2-yl] framework as sugar mimic.

Journal: Nucleosides, nucleotides & nucleic acids 20120101

Title: Identification of novel Mt-Guab2 inhibitor series active against M. tuberculosis.

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Title: Antileukemic Potential of Momordica charantia Seed Extracts on Human Myeloid Leukemic HL60 Cells.

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Title: 4-Pyridone-3-carboxamide-1-β-D-ribonucleoside triphosphate (4PyTP), a novel NAD metabolite accumulating in erythrocytes of uremic children: a biomarker for a toxic NAD analogue in other tissues?

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Title: NMNAT expression and its relation to NAD metabolism.

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Title: A comparative profile of methanol extracts of Allium cepa and Allium sativum in diabetic neuropathy in mice.

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Title: Nicotinamide riboside kinase structures reveal new pathways to NAD+.

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Title: Synthesis and antiproliferative activity of two new tiazofurin analogues with 2'-amido functionalities.

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Title: Synthesis and biological activity of some new 5'-O-acyl tiazofurin derivatives.

Journal: European journal of medicinal chemistry 20060401

Title: Metabolic regulation and chemotherapy.

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Title: Modulation of cancer pathways by inhibitors of guanylate metabolism.

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Title: Resveratrol, an ingredient of wine, acts synergistically with Ara-C and tiazofurin in HL-60 human promyelocytic leukemia cells.

Journal: Nucleosides, nucleotides & nucleic acids 20060101

Title: Zinc(II) triflate-controlled 1,3-dipolar cycloadditions of C-(2-thiazolyl)nitrones: application to the synthesis of a novel isoxazolidinyl analogue of tiazofurin.

Journal: The Journal of organic chemistry 20051028

Title: Efficient route to C2 symmetric heterocyclic backbone modified cyclic peptides.

Journal: Organic letters 20050929

Title: Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure.

Journal: Journal of pharmaceutical sciences 20050701

Title: IMP dehydrogenase from the protozoan parasite Toxoplasma gondii.

Journal: Antimicrobial agents and chemotherapy 20050601

Title: Combination of nucleoside analogues tiazofurin and ribavirin downregulates experimental autoimmune encephalomyelitis.

Journal: Annals of the New York Academy of Sciences 20050601

Title: Synergistic action of resveratrol, an ingredient of wine, with Ara-C and tiazofurin in HL-60 human promyelocytic leukemia cells.

Journal: Experimental hematology 20050301

Title: Metabolism and antiviral activity of ribavirin.

Journal: Virus research 20050201

Title: Role of human nucleoside transporters in the cellular uptake of two inhibitors of IMP dehydrogenase, tiazofurin and benzamide riboside.

Journal: Molecular pharmacology 20050101

Title: Sensitization of human erythroleukemia K562 cells resistant to methotrexate by inhibiting IMPDH.

Journal: Medical science monitor : international medical journal of experimental and clinical research 20050101

Title: Down-regulation of increased signal transduction capacity in human cancer cells.

Journal: Advances in enzyme regulation 20050101

Title: Synthesis of 3'-deoxy-3'-C-hydroxymethyl analogues of tiazofurin and ribavirin.

Journal: Nucleosides, nucleotides & nucleic acids 20050101

Title: Differentiation of human prostate cancer PC-3 cells induced by inhibitors of inosine 5'-monophosphate dehydrogenase.

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Title: Inhibition of B16 mouse melanoma cell growth and induction of apoptotic cell death with 8-chloroadenosine-3',5'-monophosphate and tiazofurin.

Journal: Annals of the New York Academy of Sciences 20041201

Title: Effects of the IMP-dehydrogenase inhibitor, Tiazofurin, in bcr-abl positive acute myelogenous leukemia. Part I. In vivo studies.

Journal: Leukemia research 20041101

Title: Effects of the IMP-dehydrogenase inhibitor, Tiazofurin, in bcr-abl positive acute myelogenous leukemia. Part II. In vitro studies.

Journal: Leukemia research 20041101

Title: Cryptosporidium parvum IMP dehydrogenase: identification of functional, structural, and dynamic properties that can be exploited for drug design.

Journal: The Journal of biological chemistry 20040924

Title: Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD+ in fungi and humans.

Journal: Cell 20040514

Title: Substitution of the conserved Arg-Tyr dyad selectively disrupts the hydrolysis phase of the IMP dehydrogenase reaction.

Journal: Biochemistry 20040420

Title: A simple assay for determining antiviral activity against Crimean-Congo hemorrhagic fever virus.

Journal: Antiviral research 20040401

Title: Cofactor mimics as selective inhibitors of NAD-dependent inosine monophosphate dehydrogenase (IMPDH)--the major therapeutic target.

Journal: Current medicinal chemistry 20040401

Title: The effects of tiazofurin on basal and amphetamine-induced motor activity in rats.

Journal: Pharmacology, biochemistry, and behavior 20040301

Title: Erythrocytotoxicity of tiazofurin in vivo and in vitro detected by scanning probe microscopy.

Journal: Toxicology letters 20040202

Title: Anticancer therapeutic potential of soy isoflavone, genistein.

Journal: Advances in experimental medicine and biology 20040101

Title: HPLC determination of tiazofurin in the rat brain.

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Title: Synthesis of 2-(3'-azido- and 3'-amino-3'-deoxy-beta-D-ribofuranosyl)thiazole-4-carboxamide.

Journal: Nucleosides, nucleotides & nucleic acids 20031101

Title: De novo synthesis of two new cytotoxic tiazofurin analogues with modified sugar moieties.

Journal: Bioorganic & medicinal chemistry letters 20031006

Title: In vitro sensitivity of hematopoietic progenitors to tiazofurin in refractory acute myeloid leukemia and in the blast crisis of chronic myeloid leukemia.

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Title: Combination therapy in childhood leukaemia: in vitro studies of thiopurines and inhibitors of purine metabolism on apoptosis.

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Title: Targeting signal transduction.

Journal: Advances in enzyme regulation 20030101

Title: A new tiazofurin pronucleotide: synthesis and biological evaluation of cyclosaligenyl-tiazofurin monophosphate.

Journal: Nucleosides, nucleotides & nucleic acids 20030101

Title: The linkage of glucose to tiazofurin decreases in vitro uptake into rat glioma C6 cells.

Journal: Journal of drug targeting 20021201

Title: Simultaneous LC determination of tiazofurin, its acetyl and benzoyl esters and their active metabolite thiazole-4-carboxamide adenine dinucleotide in biological samples.

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Title: Inhibitors of the IMPDH enzyme as potential anti-bovine viral diarrhoea virus agents.

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Title: Down-regulation of experimental allergic encephalomyelitis in DA rats by tiazofurin.

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Title: Cytoprotective features of selenazofurin in hematopoietic cells.

Journal: International journal of clinical pharmacology and therapeutics 20020801

Title: Cytotoxicity and cellular differentiation activity of methylenebis(phosphonate) analogs of tiazofurin and mycophenolic acid adenine dinucleotide in human cancer cell lines.

Journal: Cancer letters 20020708

Title: Identification of active antiviral compounds against a New York isolate of West Nile virus.

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Title: Structure of human nicotinamide/nicotinic acid mononucleotide adenylyltransferase. Basis for the dual substrate specificity and activation of the oncolytic agent tiazofurin.

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Journal: British journal of cancer 19920201

Title: Inhibitors of IMP dehydrogenase stimulate the phosphorylation of the antiviral nucleoside 2' ,3'-dideoxyguanosine.

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Title: Broad-spectrum antiviral activity of 2-beta-D-ribofuranosylselenazole-4-carboxamide, a new antiviral agent.

Journal: Antimicrobial agents and chemotherapy 19830901

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Tags:60084-10-8 Molecular Formula|60084-10-8 MDL|60084-10-8 SMILES|60084-10-8 2-b-D-Ribofuranosyl-4-thiazolecarboxamide