Home Other Building Blocks 3-DEAZAADENOSINE

3-DEAZAADENOSINE

CAS No.:
6736-58-9
Catalog Number:
AG00624S
Molecular Formula:
C11H14N4O4
Molecular Weight:
266.2533
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$112
- +
5mg
≥98%
1 week
United States
$307
- +
10mg
≥98%
1 week
United States
$501
- +
Product Description
Catalog Number:
AG00624S
Chemical Name:
3-DEAZAADENOSINE
CAS Number:
6736-58-9
Molecular Formula:
C11H14N4O4
Molecular Weight:
266.2533
MDL Number:
MFCD00153951
IUPAC Name:
(2R,3R,4S,5R)-2-(4-aminoimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChI:
InChI=1S/C11H14N4O4/c12-10-7-5(1-2-13-10)15(4-14-7)11-9(18)8(17)6(3-16)19-11/h1-2,4,6,8-9,11,16-18H,3H2,(H2,12,13)/t6-,8-,9-,11-/m1/s1
InChI Key:
DBZQFUNLCALWDY-PNHWDRBUSA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ccnc2N
UNII:
037V4520IY
Properties
Complexity:
334  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
266.102g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
266.257g/mol
Monoisotopic Mass:
266.102g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
127A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.6  
Literature
Title Journal
Relationship of impairment induced by intracellular S-adenosylhomocysteine accumulation with DNA methylation in human umbilical vein endothelial cells treated with 3-deazaadenosine. International journal of experimental pathology 20091201
Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Nature chemical biology 20091001
3-Deazaadenosine prevents smooth muscle cell proliferation and neointima formation by interfering with Ras signaling. Circulation research 20090522
TNFalpha-dependent hepatic steatosis and liver degeneration caused by mutation of zebrafish S-adenosylhomocysteine hydrolase. Development (Cambridge, England) 20090301
The nucleotide analogue 3-deazaadenosine prevents neointima-formation after balloon injury. Biochemical and biophysical research communications 20090123
3-Deazaadenosine inhibits vasa vasorum neovascularization in aortas of ApoE(-/-)/LDL(-/-) double knockout mice. Atherosclerosis 20090101
Cystathionine-beta-synthase gene transfer and 3-deazaadenosine ameliorate inflammatory response in endothelial cells. American journal of physiology. Cell physiology 20071201
Long-term administration of 3-deazaadenosine does not alter progression of advanced atherosclerotic lesions in apolipoprotein E-deficient mice. Journal of cardiovascular pharmacology 20070801
Extended storage of whole blood with 3-deazaadenosine for homocysteine assay. Annals of clinical biochemistry 20070701
Evaluation of 3-deaza-adenosine analogues as ligands for adenosine kinase and inhibitors of Mycobacterium tuberculosis growth. The Journal of antimicrobial chemotherapy 20070101
3-Deazaadenosine mitigates arterial remodeling and hypertension in hyperhomocysteinemic mice. American journal of physiology. Lung cellular and molecular physiology 20061101
Antitrypanosomal activity of 5'-deoxy-5'-(iodomethylene)adenosine and related 6-N-cyclopropyladenosine analogues. Journal of medicinal chemistry 20060323
Inhibition of transmethylation disturbs neurulation in chick embryos. Brain research. Developmental brain research 20050808
Prediction of genotoxicity of chemical compounds by statistical learning methods. Chemical research in toxicology 20050601
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. Clinical chemistry 20040901
3-Deazaadenosine prevents leukocyte invasion by suppression of adhesion molecule expression during acute cardiac allograft rejection: involvement of apoptotic cell death. The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20040801
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. Bioorganic & medicinal chemistry 20040701
Characterization of glycine N-methyltransferase from rabbit liver. Biochemistry and cell biology = Biochimie et biologie cellulaire 20040601
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. Neuromolecular medicine 20040101
Protein methylation activates reconstituted ryanodine receptor-ca release channels from coronary artery myocytes. Journal of vascular research 20040101
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. Neuromolecular medicine 20040101
Structure, evolution, and inhibitor interaction of S-adenosyl-L-homocysteine hydrolase from Plasmodium falciparum. Proteins 20030901
Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. European journal of biochemistry 20030901
On the comparison of serum and plasma samples in troponin assays. Clinical chemistry 20030501
Protective effect of 3-deazaadenosine in a rat model of lipopolysaccharide-induced myocardial dysfunction. Shock (Augusta, Ga.) 20030301
Effects of temperature on stability of blood homocysteine in collection tubes containing 3-deazaadenosine. Clinical chemistry 20021101
Effect of hyperhomocysteinemia on plasma or tissue adenosine levels and renal function. Circulation 20020903
Identification of A-minor tertiary interactions within a bacterial group I intron active site by 3-deazaadenosine interference mapping. Biochemistry 20020820
Disruption of choline methyl group donation for phosphatidylethanolamine methylation in hepatocarcinoma cells. The Journal of biological chemistry 20020510
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. Experimental & molecular medicine 20011231
Methionine depletion induces transcription of the mRNA (N6-adenosine)methyltransferase. The international journal of biochemistry & cell biology 20011101
Stabilization of blood homocysteine in an epidemiological setting. European journal of cancer prevention : the official journal of the European Cancer Prevention Organisation (ECP) 20011001
S-adenosyl-L-homocysteine hydrolase is necessary for aldosterone-induced activity of epithelial Na(+) channels. American journal of physiology. Cell physiology 20010901
Pre-analytical conditions affecting the determination of the plasma homocysteine concentration. Clinical chemistry and laboratory medicine 20010801
Structure and function of a novel purine specific nucleoside hydrolase from Trypanosoma vivax. Journal of molecular biology 20010413
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. Clinical microbiology reviews 20010401
Analysis of increased leukocyte ratio induced by tumor necrosis factor-alpha using several inhibitors in the undisturbed microcirculation of the rat mesentery. International immunopharmacology 20010301
Induction of apoptosis in human leukemia cells by 3-deazaadenosine is mediated by caspase-3-like activity. Experimental & molecular medicine 20001231
Extracellular ATP and adenosine cause apoptosis of pulmonary artery endothelial cells. The American journal of physiology 19970801
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. Biochimica et biophysica acta 19961111
Anti-human immunodeficiency virus 1 (HIV-1) activities of 3-deazaadenosine analogs: increased potency against 3'-azido-3'-deoxythymidine-resistant HIV-1 strains. Proceedings of the National Academy of Sciences of the United States of America 19950103
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues. Journal of medicinal chemistry 19940429
Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents. Journal of medicinal chemistry 19931001
Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication. Antiviral research 19930701
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives. Journal of medicinal chemistry 19921127
3-Deaza-adenosine and inhibition of HIV. Lancet (London, England) 19920215
Acyclic nucleotide analogues: synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro. Antiviral research 19900601
Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro. Antiviral research 19900101
Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro. Antiviral research 19890901
Structure-activity relationship of novel oligopeptide antiviral and antitumor agents related to netropsin and distamycin. Journal of medicinal chemistry 19860701
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 of medicinal chemistry 19841101
Broad-spectrum antiviral activity of adenosine analogues. Antiviral research 19840601
Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine. Antiviral research 19830301
Adenosine analogues as substrates and inhibitors of S-adenosylhomocysteine hydrolase. Biochemistry 19810106
Properties