78582-17-9

Basic information

• Product Name: 3-DEAZA-2'-DEOXYADENOSINE
• Synonyms: 3-DEAZA-2'-DEOXYADENOSINE;1H-Imidazo[4,5-C]pyridin-4-amine, 1-(2'-deoxy-.beta.-D-erythro-pentofuranosyl)-;3-Deaza-2'-da;Aids002055;Aids-002055
• CAS NO: 78582-17-9
• Molecular Formula: C11H14N4O3
• Molecular Weight: 250.25
• Mol File: 78582-17-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 208-209 °C
• Boiling Point: 617.7 °C at 760 mmHg
• Flash Point: 327.4 °C
• Appearance: /
• Density: 1.75 g/cm³
• Vapor Pressure: 4.05E-16mmHg at 25°C
• Refractive Index: 1.797
• PKA: 13.88±0.60(Predicted)
• CAS DataBase Reference: 3-DEAZA-2'-DEOXYADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DEAZA-2'-DEOXYADENOSINE(78582-17-9)
• EPA Substance Registry System: 3-DEAZA-2'-DEOXYADENOSINE(78582-17-9)

Safety Data

• Hazardous Substances Data: 78582-17-9(Hazardous Substances Data)

Usage

General Description

3-DEAZA-2'-DEOXYADENOSINE is a chemical compound that is structurally similar to adenosine, a nucleoside found in DNA and RNA. However, 3-DEAZA-2'-DEOXYADENOSINE does not contain a nitrogen atom at the position typically occupied by the nitrogenous base in adenosine. This modification makes it a unique molecule with potential biological and pharmacological properties. It has been studied for its potential use as an antiviral agent and as a probe for investigating the function of adenosine in biological systems. Additionally, it has been investigated for its potential role in treating cancer and various other diseases. Further research is ongoing to explore the full potential and applications of 3-DEAZA-2'-DEOXYADENOSINE in medical and scientific fields.

InChI:InChI=1/C11H14N4O3/c12-11-10-6(1-2-13-11)15(5-14-10)9-3-7(17)8(4-16)18-9/h1-2,5,7-9,16-17H,3-4H2,(H2,12,13)/t7-,8+,9+/m0/s1

Upstream product

• 106568-79-0 9-(3',5'-di-O-acetyl-2'-deoxy-β-D-erythro-pentofuranosyl)-1H-purine-6(9H)-one 
• 91184-02-0 1H-Imidazo[4,5-c]pyridine-N-oxide 
• 272-97-9 Imidazo<4,5-c>pyridin 
• 54-96-6 3,4-diaminopyridine 
• 78582-15-7 4-chloro-1-(2'-deoxy-β-D-erythro-pentofuranosyl)-1H-imidazo<4,5-c>pyridine 
• 80639-85-6 4-amino-1H-imidazo<4,5-c>pyridine dihydrochloride 
• 50-89-5 thymidine 
• 2770-01-6 4-chloro-1H-imidazo[4,5-c]pyridine 
• 78582-13-5 4-Chloro-1-<2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythropentofuranosyl>-1H-imidazo<4,5-c>pyridine 
• 144427-91-8 1-<2'-deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-4-(methylsulfonyl)-1H-imidazo<4,5-c>pyridine 
• 144427-86-1 1-<2'-deoxy-3',5'-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl>-4-(methylthio)-1H-imidazo<4,5-c>pyridine 
• 34550-50-0 4-(methylthio)-1H-imidazo<4,5-c>pyridine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 37642-56-1 5-Amino-1-(2'-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide 

Downstream Products

• 452-51-7 D-2-deoxyribose 
• 6811-77-4 3-deazaadenine 

Relevant articles and documents

Synthesis and Anti-herpetic Activity of Phosphoramidate ProTides

Among the many prodrug approaches aimed at delivering nucleoside monophosphates into cells, the phosphoramidate ProTide approach is one that has shown success, which has made it possible for some of the phosphoramidates to enter into clinical trials. Herein, we report the synthesis and antiviral activity of a series of phosphoramidate ProTides designed to bypass the thymidine kinase (TK) dependence of the parent nucleoside analogues. Phosphoramidate derivatives of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVDU) that contain L-alanine or pivaloyloxymethyl iminodiacetate (IDA-POM) exhibit anti-HSV-1 and anti-VZV activity in cell cultures, but they largely lost antiviral potency against TK-deficient virus strains. Among deazapurine nucleosides and their phosphoramidate derivatives, the 7-deazaadenine containing nucleosides and their phosphoramidate triester derivatives showed weak antiviral activity against VZV. Apparently, intracellular nucleotide delivery with these phosphoramidates is partly successful. However, none of the compound prodrugs showed superior activity to their parent drugs. Copyright

SYNTHESIS OF 2-DEOXY-β-D-RIBONUCLEOSIDES AND2,3-DIDEOXY.β-D-PENTOFURANOSIDES ON IMMOBILIZED BACTERIAL CELLS

Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs.All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N9-isomers in the purine and N1-isomers in the pyrimidine series.Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety.The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N7-nitrogen atom.On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives.Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed.The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-deoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-deoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

Synthesis of 3-deaza-2'-deoxyadenosine and 3-deaza-2',3'-dideoxyadenosine: Glycosylation of the 4-chloroimidazo[4,5-c]pyridinyl anion

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