56039-11-3

Basic information

• Product Name: 3-deazaguanosine
• Synonyms: 3-deazaguanosine
• CAS NO: 56039-11-3
• Molecular Formula: C11H14N4O5
• Molecular Weight: 282.255
• Mol File: 56039-11-3.mol

Chemical Properties

• Boiling Point: 857.9°C at 760 mmHg
• Flash Point: 472.6°C
• Appearance: /
• Density: 2.06g/cm³
• Vapor Pressure: 2.34E-31mmHg at 25°C
• Refractive Index: 1.874
• CAS DataBase Reference: 3-deazaguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deazaguanosine(56039-11-3)
• EPA Substance Registry System: 3-deazaguanosine(56039-11-3)

Safety Data

• Hazardous Substances Data: 56039-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Deazaguanosine is used as a potential antitumor agent for its ability to interfere with nucleic acid metabolism and disrupt the replication and transcription processes in cancer cells. By incorporating into DNA or RNA, it can inhibit cellular processes essential for tumor growth and proliferation, making it a valuable compound in the development of novel cancer therapies.
Additionally, 3-deazaguanosine is used as an antiviral agent due to its capacity to inhibit viral replication. By mimicking guanosine, it can be incorporated into viral nucleic acids, leading to the termination of the viral replication process. This property makes 3-deazaguanosine a promising candidate for the development of new antiviral drugs to combat various viral infections.

InChI:InChI=1/C11H14N4O5/c12-6-1-4-7(10(19)14-6)13-3-15(4)11-9(18)8(17)5(2-16)20-11/h1,3,5,8-9,11,16-18H,2H2,(H3,12,14,19)/t5-,8-,9-,11-/m1/s1

Upstream product

• 99422-54-5 methyl 2-chloro-5-trimethylsilyl-1-(2,3-O-methoxymethylidene-5-O-TBDMS-β-D-ribofuranosyl)imidazole-4-carboxylate 
• 99409-52-6 methyl 2-chloro-5-hydroxymethyl-1-(2,3-O-methoxymethylidene-5-O-TBDMS-β-D-ribofuranosyl)imidazole-4-carboxylate 
• 99409-54-8 methyl 5-cyanomethyl-1-(2,3-O-methoxymethylidene-5-O-TBDMS-β-D-ribofuranosyl)imidazole-4-carboxylate 
• 99422-55-6 methyl 5-chloromethyl-1-(2,3-O-methoxymethylidene-5-O-TBDMS-β-D-ribofuranosyl)imidazole-4-carboxylate 
• 99409-53-7 methyl 5-hydroxymethyl-1-(2,3-O-methoxymethylidene-5-O-TBDMS-β-D-ribofuranosyl)imidazole-4-carboxylate 
• 99409-48-0 methyl 2-chloro-1-(2,3-O-methoxymethylidene-5-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazole-4-carboxylate 
• 99409-47-9 methyl 2-chloro-1-(2,3-O-methoxymethylidene-β-D-ribofuranosyl)imidazole-4-carboxylate 
• 147212-81-5 5-cyanomethyl-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 147212-80-4 5-(2-hydroxyiminoethyl)-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 147212-71-3 5-ethynyl-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 118908-07-9 5-ethynyl-1-(β-D-ribofuranosyl)imidazole-4-carboxamide 
• 58931-20-7 methyl 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate 
• 147212-82-6 6-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo<4,5-c>pyridin-4(5H)-one 
• 99409-55-9 6-amino-1-(2,3-O-methoxymethylidene-5-O-TBDMS-β-D-ribofuranosyl)imidazo(4,5-c)pyridin-4(5H)-one 

Relevant articles and documents

LITHIATION OF AN IMIDAZOLE NUCLEOSIDE AT THE C-5 POSITION. SYNTHESIS OF 3-DEAZAGUANOSINE FROM URIDINE

3-Deazaguanosine, an antiviral nucleoside, was synthesized from uridine via lithiation of a C-2 protected imidazole nucleoside, which has been devised as a method for introducing various functionalities to the C-5 position.This furnished the first success

Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase

The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

Nucleosides and Nucleotides. 116. Convenient Syntheses of 3-Deazaadenosine, 3-Deazaguanosine, and 3-Deazainosine via Ring Closure of 5-Ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide or -carbonitrile

An easy chemical synthesis of 3-deazapurine nucleosides, 3-deazainosine pyridin-4(5H)-one (8)>, 3-deazaguanosine pyridin-4(5H)-one (23)>, and 3-deazaadenosine 4-amino-1-β-D-ribof

Nucleosides and nucleotides. 114. A convenient method for the synthesis of 3-deazapurine nucleosides from AICA-riboside

3-Deazapurine nucleosides, 3-deazaguanosine (6) 3-deazaguanosine (12) and 3-deazaadenosine (17), were synthesized from 5-ethynyl-1- β-D-ribofuranosylimidazole-4-carboxamide (2) or -4-carbonitrile (13), which were readily obtained from AICA-riboside, via intramolecular ring closure.

Synthesis and Antiviral/Antitumor Activities of Certain 3-Deazaguanine Nucleosides and Nucleotides

A new procedure for the preparation of the antiviral and antitumor agent 3-deazaguanine (1) and its metabolite 3-deazaguanosine (2) has been developed by reacting methyl 5(4)-(cyanomethyl)imidazole-4(5)-carboxylate (4) and 5-(cyanomethyl)-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazole-4-carboxylate (6), respectively, with hydrazine.The 3-deazaguanosine 3',5'-cyclic phosphate (13) was prepared from 5-(cyanomethyl)-1-β-D-ribofuranosylimidazole-4-carboxamide 5'-phosphate.Glycosylation of the trimethylsilyl 4 with 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-D-ribofuranose in the presence of trimethylsilyl trifluoromethanesulfonate gave the corresponding N-1 and N-3 glycosyl derivatives with α-configuration (18 and 20) as the major products, along with minor amounts of the β-anomers (19 and 21).However, glycosylation of the sodium salt of 4 with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose (17) gave exclusively the β-anomers (19 and 21) in good yield.Base-catalyzed ring closure of these imidazole nucleosides gave 2'-deoxy-3-deazaguanosine (29), the α-anomer 28, and the corresponding N-3 positional isomers 27 and 26.The site of glycosylation and the anomeric configuration of these nucleosides have been assigned on the basis of 1H NMR and UV spectral characteristics and by single-crystal X-ray analysis for 27-29.In a preliminary screening, several of these compounds have demonstrated significant broad-spectrum antiviral activity against certain DNA and RNA viruses in vitro, as well as moderate activity against L1210 and P388 leukemia in cell culture.