163152-53-2

Basic information

• Product Name: 7-chloro-1-beta-D-ribofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine
• CAS NO: 163152-53-2
• Molecular Formula: C₁₁H₁₃ClN₄O₄
• Molecular Weight: 300.6983
• Mol File: 163152-53-2.mol

Chemical Properties

• Boiling Point: 673.6°C at 760 mmHg
• Flash Point: 361.2°C
• Density: 2.02g/cm³
• Vapor Pressure: 4.6E-19mmHg at 25°C
• Refractive Index: 1.843
• CAS DataBase Reference: 7-chloro-1-beta-D-ribofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-1-beta-D-ribofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine(163152-53-2)
• EPA Substance Registry System: 7-chloro-1-beta-D-ribofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine(163152-53-2)

Safety Data

• Hazardous Substances Data: 163152-53-2(Hazardous Substances Data)

Upstream product

• 163152-62-3 4-acetamido-7-chloro-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo[4,5-c]pyridine 
• 163152-61-2 4-acetamido-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo[4,5-c]pyridine 
• 147212-86-0 4-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo<4,5-c>pyridine 
• 405231-09-6 4,7-dichloro-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)imidazo[4,5-c]pyridine 
• 405231-11-0 4,7-dichloro-1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridine 
• 405231-24-5 1-[(1-acetyloxy-1-ethoxy)methyl]-4,7-dichloroimidazo[4,5-c]pyridine 
• 405230-91-3 4-amino-2,5-dichloro-3-nitropyridine 
• 405230-94-6 3,4-diamino-2,5-dichloropyridine 
• 405230-87-7 2,5-dichloro-4-nitraminopyridine 
• 405230-98-0 4,7-dichloroimidazo[4,5-c]pyridine 
• 405230-81-1 2,5-dichloro-4-nitropyridine-1-oxide 
• 405230-82-2 2,5-dichloro-4-amino-pyridine 
• 16110-09-1 2,5 dichloropyridine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Relevant articles and documents

Nucleosides and nucleotides. 184. Synthesis and conformational investigation of anti-fixed 3-deaza-3-halopurine ribonucleosides

A versatile synthetic route to 3-deaza-3-haloinosines 6-8 and 46, - adenosines 15-17 and 64, and -guanosines 25, 26, and 52 is described. 3- Deaza-3-chloro-, -bromo-, and -iodopurine ribonucleosides can be synthesized by treating the 3-deazapurine ribonucleosides with N-halosuccinimides. For the synthesis of 3-deaza-3-fluoropurine ribonucleosides, 5-formylimidazole-4- carboxamide ribosides 34 and 35 prepared from 5-iodoimidazole-4-carboxamide derivatives 29 and 31 were used as the key intermediates. The reaction of 34 and 35 with lithium (trimethylsilyl)acetylide and sodium cyanide, respectively, followed by appropriate manipulations gave 3-deaza-3- fluoroinosine derivative 46 and 3-deaza-3-fluoroguanosine derivative 52. 3- Deaza-3-fluoroadenosine (64) was also synthesized by selective reductive deamination of 4,6-diamino-7-fluoroimidazo[4,5-c]pyridine derivative 51, followed by deprotection. A conformational analysis using 1H NMR and NOE experiments showed that the introduction of halogens (chloro, bromo, and iodo) into the 3-position of 3-deazapurine ribonucleosides forced fixation of the glycosyl torsion angle in the anti region, but did not abnormally influence sugar puckering. On the other hand, 3-deaza-3-fluoropurine ribonucleosides should rotate freely around the glycosyl bond.

Novel nucleosides and related processes, pharmaceutical compositions and methods

The invention provides novel nucleosides and related processes, pharmaceutical compositions, and methods. The novel nucleosides are useful in a wide variety of antiviral, antineoplastic, and antibacterial applications. Preferred embodiments of the instant invention include novel 2 halogen-substituted, 3 halogen-substituted, and 2′,3′dihalogen-substituted analogues of 3-deazaadenosine, and novel 3 halogen-substituted analogues of 3-deazaguanosine. Compounds of the instant invention, including 4-Amino-6-fluoro-1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridine and 6-Amino-7-bromo-1,5-dihydro-1-β-D-ribofuranosylimidazo[4,5-c]pyridin-4-one, have exhibited potent antiviral and anticancer activity in vitro. The compounds are also useful in the concomitant treatment of bacterial infections associated with viral infections such as AIDS.

Synthesis of halogen-substituted 3-deazaadenosine and 3-deazaguanosine analogues as potential antitumor/antiviral agents

Various 2-halogen-substituted analogues (38, 39, 43 and 44), 3-halogensubstituted analogues (51 and 52), and 2′,3′ -dihalogen- substituted analogues (57-60) of 3-deazaadenosine and 3-halogen-substituted analogues (61 and 62) of 3-deazaguanosine have been synthesized as potential anticancer and/or antiviral agents. Among these compounds, 3-deaza-3-bromoguanosine (62) showed significant cytotoxicity against L1210, P388, CCRF-CEM and B16F10 cell lines in vitro, producing IC50 values of 3, 7, 9 and 7μM, respectively. Several 3-deazaadenosine analogues (38, 51, 57 and 59) showed moderate to weak activity against hepatitis B virus.