87202-41-3

Basic information

• Product Name: 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one
• Synonyms: 4H-Imidazo(4,5-c)pyridin-4-one, 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,5-dihydro-; 4H-Imidazo[4,5-c]pyridin-4-one, 6-amino-1-(2-deoxy-.beta.-D-erythro-pentofuranosyl)-1,5-dihydro-
• CAS NO: 87202-41-3
• Molecular Formula: C₁₁H₁₄N₄O₄
• Molecular Weight: 266.2533
• Mol File: 87202-41-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 806.4°C at 760 mmHg
• Flash Point: 441.5°C
• Density: 1.9g/cm³
• Vapor Pressure: 1.83E-27mmHg at 25°C
• Refractive Index: 1.834
• CAS DataBase Reference: 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one(87202-41-3)
• EPA Substance Registry System: 6-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,5-dihydro-4H-imidazo[4,5-c]pyridin-4-one(87202-41-3)

Safety Data

• Hazardous Substances Data: 87202-41-3(Hazardous Substances Data)

Upstream product

• 56039-06-6 methyl 5-(cyanomethyl)-1H-imidazole-4-carboxylate 
• 3601-89-6 Hoffer's chlorosugar 
• 170871-02-0 5-amino-1-(3,5-di-O-tert-butyldimethylsilyl-2-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 106568-79-0 9-(3',5'-di-O-acetyl-2'-deoxy-β-D-erythro-pentofuranosyl)-1H-purine-6(9H)-one 
• 890-38-0 2-deoxyinosine 
• 175787-21-0 6-Amino-1-[(2R,4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,5-dihydro-imidazo[4,5-c]pyridin-4-one 
• 83587-61-5 5-(cyanomethyl)-1-(2-deoxy-β-D-erythro-pentofuranosyl)imidazole-4-carboxamide 
• 91713-27-8 methyl 5-(cyanomethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)imidazole-4-carboxylate 
• 229326-12-9 Acetic acid (2R,3S,5R)-3-hydroxy-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester 
• 37642-56-1 5-Amino-1-(2'-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide 
• 175787-17-4 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-trimethylsilanylethynyl-1H-imidazole-4-carboxylic acid amide 
• 175787-19-6 1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-(2-hydroxyimino-ethyl)-1H-imidazole-4-carboxylic acid amide 
• 175787-15-2 5-iodo-1-(2-deoxy-3,5-di-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazole-4-carboxamide 

Downstream Products

• 139340-17-3 1-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-<(2-methylpropionyl)amino>-1H-imidazo<4,5-c>pyridin-4(5H)-one 3'-(triethylammonium phosphonate) 
• 139340-18-4 1-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-(<(dimethylamino)methylidene>amino)-1H-imidazo<4,5-c>pyridin-4(5H)-one 3'-(triethylammonium phosphonate) 
• 139212-54-7 1-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-(<(dimethylamino)methylidene>amino)-1H-imidazo<4,5-c>pyridin-5(5H)-one 3'-<(2-cyanoethyl)N,N-diisopropylphosphoramidite> 
• 139212-47-8 1-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-<(2-methylpropionyl)amino>-1H-imidazo<4,5-c>pyridin-4(5H)-one 
• 139212-52-5 1-<2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl>-6-(<(dimethylamino)methylidene>amino)-1H-imidazo<4,5-c>pyridin-4(5H)-one 

Relevant articles and documents

Nucleosides and nucleotides. 143. Synthesis of 5-amino-4- imidazolecarboxamide (AICA) deoxyribosides from deoxyinosines and their conversion into 3-deazapurine derivatives

An efficient and large scale chemical synthesis of 5-aminoimidazole-4- carboxamide (AICA) 2'-deoxyriboside (5a) and its 3'-deoxyriboside 5b is described. Treatment of 3',5'-di-O-acetyl-N1-triphenylmethyl-2'-deoxyinosine (3a) with 5N NaOH in EtOH, followed by anhydrous trifluoroacetic acid gave 5a in 59% yield from 2'-deoxyinosine (1a). AICA 3'-deoxyriboside (5b) was also obtained in a similar manner as for 5a in 73% yield from 3'-deoxyinosine (1b). Conversion of these AICA derivatives (5a, b) into 3-deazapurine derivatives (9a, b, 15a, b, 20a, b) is also described.

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.