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6736-58-9,MFCD00153951
Catalog No.:AA006220

6736-58-9 | 3-DEAZAADENOSINE

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA006220
Chemical Name:
3-DEAZAADENOSINE
CAS Number:
6736-58-9
Molecular Formula:
C11H14N4O4
Molecular Weight:
266.2533
MDL Number:
MFCD00153951
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ccnc2N
Properties
Properties
 
Form:
Solid  
MP:
222-224°C  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
334  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
2  
XLogP3:
-1.6  

Downstream Synthesis Route

[1]Hennen;Wong[JournalofOrganicChemistry,1989,vol.54,#19,p.4692-4695]

[1]Hennen;Wong[JournalofOrganicChemistry,1989,vol.54,#19,p.4692-4695]

[1]Krenitsky;Rideout;Chao;Koszalka;Gurney;Crouch;Cohn;Wolberg;Vinegar[JournalofMedicinalChemistry,1986,vol.29,#1,p.138-143]

[1]Hennen;Wong[JournalofOrganicChemistry,1989,vol.54,#19,p.4692-4695]

[1]JournalofMedicinalChemistry,1986,vol.29,p.138-143

[2]EuropeanJournalofMedicinalChemistry,2018,vol.148,p.384-396

Literature

Title: Relationship of impairment induced by intracellular S-adenosylhomocysteine accumulation with DNA methylation in human umbilical vein endothelial cells treated with 3-deazaadenosine.

Journal: International journal of experimental pathology 20091201

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: 3-Deazaadenosine prevents smooth muscle cell proliferation and neointima formation by interfering with Ras signaling.

Journal: Circulation research 20090522

Title: TNFalpha-dependent hepatic steatosis and liver degeneration caused by mutation of zebrafish S-adenosylhomocysteine hydrolase.

Journal: Development (Cambridge, England) 20090301

Title: The nucleotide analogue 3-deazaadenosine prevents neointima-formation after balloon injury.

Journal: Biochemical and biophysical research communications 20090123

Title: 3-Deazaadenosine inhibits vasa vasorum neovascularization in aortas of ApoE(-/-)/LDL(-/-) double knockout mice.

Journal: Atherosclerosis 20090101

Title: Cystathionine-beta-synthase gene transfer and 3-deazaadenosine ameliorate inflammatory response in endothelial cells.

Journal: American journal of physiology. Cell physiology 20071201

Title: Long-term administration of 3-deazaadenosine does not alter progression of advanced atherosclerotic lesions in apolipoprotein E-deficient mice.

Journal: Journal of cardiovascular pharmacology 20070801

Title: Extended storage of whole blood with 3-deazaadenosine for homocysteine assay.

Journal: Annals of clinical biochemistry 20070701

Title: Evaluation of 3-deaza-adenosine analogues as ligands for adenosine kinase and inhibitors of Mycobacterium tuberculosis growth.

Journal: The Journal of antimicrobial chemotherapy 20070101

Title: 3-Deazaadenosine mitigates arterial remodeling and hypertension in hyperhomocysteinemic mice.

Journal: American journal of physiology. Lung cellular and molecular physiology 20061101

Title: Antitrypanosomal activity of 5'-deoxy-5'-(iodomethylene)adenosine and related 6-N-cyclopropyladenosine analogues.

Journal: Journal of medicinal chemistry 20060323

Title: Inhibition of transmethylation disturbs neurulation in chick embryos.

Journal: Brain research. Developmental brain research 20050808

Title: Prediction of genotoxicity of chemical compounds by statistical learning methods.

Journal: Chemical research in toxicology 20050601

Title: 3-Deazaadenosine, a stabilizer of whole-blood homocysteine content, does not interfere with the single-enzyme homocysteine assay while totally inhibiting the enzyme conversion homocysteine immunoassay.

Journal: Clinical chemistry 20040901

Title: 3-Deazaadenosine prevents leukocyte invasion by suppression of adhesion molecule expression during acute cardiac allograft rejection: involvement of apoptotic cell death.

Journal: The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20040801

Title: 3-Deazaadenosine analogues of p5'A2'p5'A2'p5'A: synthesis, stereochemistry, and the roles of adenine ring nitrogen-3 in the interaction with RNase L.

Journal: Bioorganic & medicinal chemistry 20040701

Title: Characterization of glycine N-methyltransferase from rabbit liver.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire 20040601

Title: The S-adenosyl homocysteine hydrolase inhibitor 3-deaza-adenosine prevents oxidative damage and cognitive impairment following folate and vitamin E deprivation in a murine model of age-related, oxidative stress-induced neurodegeneration.

Journal: Neuromolecular medicine 20040101

Title: Protein methylation activates reconstituted ryanodine receptor-ca release channels from coronary artery myocytes.

Journal: Journal of vascular research 20040101

Title: Dietary supplementation with 3-deaza adenosine, N-acetyl cysteine, and S-adenosyl methionine provide neuroprotection against multiple consequences of vitamin deficiency and oxidative challenge: relevance to age-related neurodegeneration.

Journal: Neuromolecular medicine 20040101

Title: Structure, evolution, and inhibitor interaction of S-adenosyl-L-homocysteine hydrolase from Plasmodium falciparum.

Journal: Proteins 20030901

Title: Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners.

Journal: European journal of biochemistry 20030901

Title: On the comparison of serum and plasma samples in troponin assays.

Journal: Clinical chemistry 20030501

Title: Protective effect of 3-deazaadenosine in a rat model of lipopolysaccharide-induced myocardial dysfunction.

Journal: Shock (Augusta, Ga.) 20030301

Title: Effects of temperature on stability of blood homocysteine in collection tubes containing 3-deazaadenosine.

Journal: Clinical chemistry 20021101

Title: Effect of hyperhomocysteinemia on plasma or tissue adenosine levels and renal function.

Journal: Circulation 20020903

Title: Identification of A-minor tertiary interactions within a bacterial group I intron active site by 3-deazaadenosine interference mapping.

Journal: Biochemistry 20020820

Title: Disruption of choline methyl group donation for phosphatidylethanolamine methylation in hepatocarcinoma cells.

Journal: The Journal of biological chemistry 20020510

Title: Activation of caspase-8 in 3-deazaadenosine-induced apoptosis of U-937 cells occurs downstream of caspase-3 and caspase-9 without Fas receptor-ligand interaction.

Journal: Experimental & molecular medicine 20011231

Title: Methionine depletion induces transcription of the mRNA (N6-adenosine)methyltransferase.

Journal: The international journal of biochemistry & cell biology 20011101

Title: Stabilization of blood homocysteine in an epidemiological setting.

Journal: European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20011001

Title: S-adenosyl-L-homocysteine hydrolase is necessary for aldosterone-induced activity of epithelial Na(+) channels.

Journal: American journal of physiology. Cell physiology 20010901

Title: Pre-analytical conditions affecting the determination of the plasma homocysteine concentration.

Journal: Clinical chemistry and laboratory medicine 20010801

Title: Structure and function of a novel purine specific nucleoside hydrolase from Trypanosoma vivax.

Journal: Journal of molecular biology 20010413

Title: Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections.

Journal: Clinical microbiology reviews 20010401

Title: Analysis of increased leukocyte ratio induced by tumor necrosis factor-alpha using several inhibitors in the undisturbed microcirculation of the rat mesentery.

Journal: International immunopharmacology 20010301

Title: Induction of apoptosis in human leukemia cells by 3-deazaadenosine is mediated by caspase-3-like activity.

Journal: Experimental & molecular medicine 20001231

Title: Extracellular ATP and adenosine cause apoptosis of pulmonary artery endothelial cells.

Journal: The American journal of physiology 19970801

Title: The role of phosphatidylethanolamine methylation in the secretion of very low density lipoproteins by cultured rat hepatocytes: rapid inhibition of phosphatidylethanolamine methylation by bezafibrate increases the density of apolipoprotein B48-containing lipoproteins.

Journal: Biochimica et biophysica acta 19961111

Title: Anti-human immunodeficiency virus 1 (HIV-1) activities of 3-deazaadenosine analogs: increased potency against 3'-azido-3'-deoxythymidine-resistant HIV-1 strains.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19950103

Title: Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.

Journal: Journal of medicinal chemistry 19940429

Title: Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents.

Journal: Journal of medicinal chemistry 19931001

Title: Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication.

Journal: Antiviral research 19930701

Title: Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.

Journal: Journal of medicinal chemistry 19921127

Title: 3-Deaza-adenosine and inhibition of HIV.

Journal: Lancet (London, England) 19920215

Title: Acyclic nucleotide analogues: synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro.

Journal: Antiviral research 19900601

Title: Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro.

Journal: Antiviral research 19900101

Title: Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro.

Journal: Antiviral research 19890901

Title: Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin.

Journal: Journal of medicinal chemistry 19860701

Title: Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.

Journal: Journal of medicinal chemistry 19841101

Title: Broad-spectrum antiviral activity of adenosine analogues.

Journal: Antiviral research 19840601

Title: Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine.

Journal: Antiviral research 19830301

Title: Adenosine analogues as substrates and inhibitors of S-adenosylhomocysteine hydrolase.

Journal: Biochemistry 19810106

Title: Gordon RK, et al. Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur J Biochem. 2003 Sep;270(17):3507-17.

Title: Jeong SY, et al. 3-deazaadenosine, a S-adenosylhomocysteine hydrolase inhibitor, has dual effects on NF-kappaB regulation. Inhibition of NF-kappaB transcriptional activity and promotion of IkappaBalpha degradation. J Biol Chem. 1999 Jul 2;274(27):18981-8.

Title: Sedding DG, et al. 3-Deazaadenosine prevents smooth muscle cell proliferation and neointima formation by interfering with Ras signaling. Circ Res. 2009 May 22;104(10):1192-200.

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