333447-52-2

Basic information

• Product Name: 1-(3,5-bis-O-(p-chlorobenzoyl)-2'-deoxy-α-D-ribofuranosyl)-5-bromo-2,4-difluorobenzene
• Synonyms: 1-(3,5-bis-O-(p-chlorobenzoyl)-2'-deoxy-α-D-ribofuranosyl)-5-bromo-2,4-difluorobenzene
• CAS NO: 333447-52-2
• Molecular Weight: 586.214
• Mol File: 333447-52-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(3,5-bis-O-(p-chlorobenzoyl)-2'-deoxy-α-D-ribofuranosyl)-5-bromo-2,4-difluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,5-bis-O-(p-chlorobenzoyl)-2'-deoxy-α-D-ribofuranosyl)-5-bromo-2,4-difluorobenzene(333447-52-2)
• EPA Substance Registry System: 1-(3,5-bis-O-(p-chlorobenzoyl)-2'-deoxy-α-D-ribofuranosyl)-5-bromo-2,4-difluorobenzene(333447-52-2)

Safety Data

• Hazardous Substances Data: 333447-52-2(Hazardous Substances Data)

Upstream product

• 122-01-0 4-chloro-benzoyl chloride 
• 348-57-2 2,4-difluorobromobenzene 
• 28342-75-8 1,5-dibromo-2,4-difluorobenzene 
• 21740-23-8 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride 

Downstream Products

• 333447-53-3 1-(3,5-bis-O-(p-chlorobenzoyl)-2'-deoxy-β-D-ribofuranosyl)-5-bromo-2,4-difluorobenzene 

Relevant articles and documents

Synthesis of 1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5- substituted-benzene thymidine mimics, some related α-anomers, and their evaluation as antiviral and anticancer agents

A group of unnatural 1-(2-deoxy-β-D-ribofuranosyl)-2.4-difluorobenzenes having a variety of C-5 substituents (H, Me, F, Cl, Br, I, CF3, CN, NO2, NH2), designed as thymidine mimics, were synthesized for evaluation as anticancer and antiviral agents. The coupling reaction of 3,5-bis-O-(p-chlorobenzoyl) 2-deoxy-α-D-ribofuranosyl chloride with an organocadmium reagent [(2,4-difluorophenyl)2Cd] afforded a mixture of the α- and β-anomeric products (α:β = 3:1 to 10:1 ratio). Treatment of the α-anomer with BF3·Et2O in nitroethane at 110-120°C for 30 min was developed as an efficient method for epimerization of the major α-anomer to the desired β-anomer. The 5-substituted (H, Me, Cl, I, NH2) β-anomers exhibited negligible cytotoxicity in a MTT assay (CC50 = 10-3-10-4 M range), relative to thymidine (CC50 = 10-3-10-5 M range), against a variety of cancer cell lines. In contrast, the 5-NO2 derivative was more cytotoxic (CC50 = 10-5-10-6 M range). A number of 5-substituted β-anomers, and some related α-anomers, that were evaluated using a wide variety of antiviral assay systems [HSV-1, HSV-2, varicella-zoster virus (VZV), vaccinia virus, vesicular stomatitis, cytomegalovirus (CMV) and human immunodeficiency (HIV-1, HIV-2) viruses], showed that this class of unnatural C-aryl nucleoside mimics are inactive antiviral agents.