1055168-98-3

Basic information

• Product Name: 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine
• Synonyms: 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine
• CAS NO: 1055168-98-3
• Molecular Weight: 614.014
• Mol File: 1055168-98-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine(1055168-98-3)
• EPA Substance Registry System: 6-amino-2-chloro-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine(1055168-98-3)

Safety Data

• Hazardous Substances Data: 1055168-98-3(Hazardous Substances Data)

Upstream product

• 58-96-8 uridine 
• 1839-18-5 2-chloroadenine 
• 118-00-3 G 
• 146-77-0 2-Chloroadenosine 
• 98-88-4 benzoyl chloride 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Downstream Products

• 123318-82-1 clofarabine 
• 355138-50-0 6-amino-2-chloro-9-(2'-deoxy-2'-fluoro-3',5'-di-O-benzoyl-β-D-arabinofuranosyl)-9H-purine 
• 1353040-42-2 2-chloro-9-(3',5'-di-O-benzoyl-β-D-ribofuranosyl)adenine 
• 1353040-41-1 2-chloro-9-(2',5'-di-O-benzoyl-β-D-ribofuranosyl)adenine 
• 1353040-43-3 2-chloro-9-(3',5'-di-O-benzoyl-2'-O-trifluoromethylsulfonyl-β-D-ribofuranosyl)adenine 
• 1093278-65-9 2-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-chloro-β-D-arabinofuranosyl)-adenine 
• 146-77-0 2-Chloroadenosine 
• 15763-11-8 2-hydrazinoadenosine 

Relevant articles and documents

Discovery of novel purine nucleoside derivatives as phosphodiesterase 2 (PDE2) inhibitors: Structure-based virtual screening, optimization and biological evaluation

Phosphodiesterase 2 (PDE2) has received much attention for the potential treatment of the central nervous system (CNS) disorders and pulmonary hypertension. Herein, we identified that clofarabine (4), an FDA-approved drug, displayed potential PDE2 inhibitory activity (IC50 = 3.12 ± 0.67 μM) by structure-based virtual screening and bioassay. Considering the potential therapeutic benefit of PDE2, a series of purine nucleoside derivatives based on the structure and binding mode of 4 were designed, synthesized and evaluated, which led to the discovery of the best compound 14e with a significant improvement of inhibitory potency (IC50 = 0.32 ± 0.04 μM). Further molecular docking and molecular dynamic (MD) simulations studies revealed that 5′-benzyl group of 14e could interact with the unique hydrophobic pocket of PDE2 by forming extra van der Waals interactions with hydrophobic residues such as Leu770, Thr768, Thr805 and Leu809, which might contribute to its enhancement of PDE2 inhibition. These potential compounds reported in this article and the valuable structure-activity relationships (SARs) might bring significant instruction for further development of potent PDE2 inhibitors.

Preparation of 2-chloro-9-(2'-deoxy-2'-fluoro-Beta-D-arabinofuranosyl)-adenine

A process for making clofarabine comprising: fluorinating a compound of formula VII wherein each R4 is independently a hydroxy protecting group, OR6 is a leaving group, with a fluorinating agent in the presence of guanidine carbonate to give a compound of formula VIII: wherein R4 is as defined above; and deprotecting the compound of formula VIII to give the clofarabine.