871671-47-5

Basic information

• Product Name: 4-chloro-7-(5-deoxy-2,3-O-isopropylidenyl-β-D-ribofuranosyl)-5-phenylpyrrolo[2,3-d]pyrimidine
• Synonyms: 4-chloro-7-(5-deoxy-2,3-O-isopropylidenyl-β-D-ribofuranosyl)-5-phenylpyrrolo[2,3-d]pyrimidine
• CAS NO: 871671-47-5
• Molecular Weight: 385.85
• Mol File: 871671-47-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-chloro-7-(5-deoxy-2,3-O-isopropylidenyl-β-D-ribofuranosyl)-5-phenylpyrrolo[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-7-(5-deoxy-2,3-O-isopropylidenyl-β-D-ribofuranosyl)-5-phenylpyrrolo[2,3-d]pyrimidine(871671-47-5)
• EPA Substance Registry System: 4-chloro-7-(5-deoxy-2,3-O-isopropylidenyl-β-D-ribofuranosyl)-5-phenylpyrrolo[2,3-d]pyrimidine(871671-47-5)

Safety Data

• Hazardous Substances Data: 871671-47-5(Hazardous Substances Data)

Upstream product

• 54760-24-6 2-amino-4-phenyl-1H-pyrrole-3-carboxylic acid amide 
• 158112-53-9 (3aR,6R,6aR)-2,2,6-trimethyltetrahydro-2H-furo(3,4-d)(1,3)dioxol-4-ol 
• 54153-51-4 2-amino-3-cyano-4-phenylpyrrole 
• 871671-45-3 5-phenylpyrrolo-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one 
• 208459-81-8 4-chloro-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 291535-34-7 5-deoxy-2,3-O-isopropylidene-α-D-ribofuranosyl chloride 

Downstream Products

• 871672-05-8 4-N-(N-cyclopropylthionocarbamoylmethyl)amino-5-phenyl-7-(5-deoxy-2,3-O-isopropylidenyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 871671-59-9 4-N-(N-cyclopropylcarbamoylmethyl)amino-5-phenyl-7-(5-deoxy-2,3-O-isopropylidenyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Adenosine kinase inhibitors. 6. Synthesis, water solubility, and antinociceptive activity of 5-phenyl-7-(5-deoxy-β-d-ribofuranosyl) pyrrolo[2,3-d]pyrimidines substituted at C4 with glycinamides and related compounds

4-(Phenylamino)-5-phenyl-7-(5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d] pyrimidine (1) and related compounds known as "diaryltubercidin" analogues are potent inhibitors of adenosine kinase (AK) and are orally active in animal models of pain such as the rat formalin paw model (GP3269 ED 50 = 6.4 mg/kg). However, the utility of this compound class is limited by poor water solubility that can be attributed to the high energy of crystallization caused by stacking of the parallel C4 and C5 aryl rings in the solid state (compound 1 and GP3269 each with pH 7.4 solubility 50 = 3 nM and water solubility = 32 ± 9 μg/mL at pH 7.4), was further characterized in biological assays. Compound 16c exhibited strong oral efficacy in the rat formalin paw model (ED50 of 2.5 mg/kg). In the most advanced assay, 16c was found to inhibit bradykinin-induced licking in marmoset monkeys with an ED50 estimated at 0.9 mg/kg without producing evidence of side effects such as ataxia, sedation, and emesis at this dose. However, lethal toxicity in the rat formalin paw model occurred with high doses of 16c, and further work on this series was discontinued.