5964-40-9

Basic information

• Product Name: 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil
• Synonyms: 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil
• CAS NO: 5964-40-9
• Molecular Weight: 452.51
• Mol File: 5964-40-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil(5964-40-9)
• EPA Substance Registry System: 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil(5964-40-9)

Safety Data

• Hazardous Substances Data: 5964-40-9(Hazardous Substances Data)

Upstream product

• 76-83-5 trityl chloride 
• 951-78-0 2'-deoxyuridine 
• 5983-03-9 3'-O-(methylsulfonyl)-5'-O-trityl-2'-deoxyuridine 
• 14270-73-6 O^5'-trityl-2'-deoxy-uridine 
• 6038-53-5 1-<2-deoxy-3-O-methanesulfonyl-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>uracil 

Downstream Products

• 84472-84-4 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)uracil 
• 859206-78-3 3'-amino-5'-O-trityl-2',3'-dideoxyuridine 
• 859206-79-4 3'-acetylamino-5'-O-trityl-2',3'-dideoxyuridine 
• 84472-86-6 3'-amino-2',3'-dideoxyuridine 

Relevant articles and documents

Modified 5'-Trityl Nucleosides as Inhibitors of Plasmodium falciparum dUTPase

2'-Deoxyuridine triphosphate nucleotidohydrolase (dUTPase) is a potential drug target for the treatment of malaria. We previously reported the discovery of 5'-tritylated analogues of deoxyuridine as selective inhibitors of this Plasmodium falciparum enzyme. Herein we report further structure-activity studies; in particular, variations of the 5'-trityl group, the introduction of various substituents at the 3'-position of deoxyuridine, and modifications of the base. Compounds were tested against both the enzyme and the parasite. Variations of the 5'-trityl group and of the 3'-substituent were well tolerated and yielded active compounds. However, there is a clear requirement for the uracil base for activity, because modifications of the uracil ring result in loss of enzyme inhibition and significant decreases in antiplasmodial action. Fewer trips to the dUMP: dUTPase is a potential drug target for the treatment of malaria. We previously reported the discovery of 5'-tritylated analogues of deoxyuridine as selective inhibitors of this P.falciparum enzyme. Herein we report further structure-activity studies of the 5'-trityl group, the introduction of various substituents at the 3'-position of deoxyuridine, and modifications of the base.

A facile one-pot synthesis of 2,3'-anhydro-2'-deoxyuridines via 3'-O-imidazolylsulfonates

Continued interests in the novel synthetic methods of the pivotal compound, 2,3'-anhydro-2'-deoxyribonucleosides (7) uncovered a facile one-pot conversion of 5 with 1,1'-sulfonyldiimidazole in basic conditions to 7 with almost quantitative yields (91-99%).

Synthesis and biological activity of 3'-azido- and 3'-amino substituted nucleoside analogs

The product distribution obtained in the reaction of 1-(5-0-trityl-0-mesyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,4-(1H, 3H)-pyrimidinedione with lithium azide in N, N'-dimethylformamide at 100°C depends on the nature of the substituent in 5. The results may be explained by a difference in the acidity of the pyrimidinedione. The reaction of the more acidic nucleosides (X = I, F) appears to proceed preferentially through the 2,3'-anhydro intermediate, whereas for the less acidic products (X = H, CH3) direct nucleophilic displacement by the azide ion predominates. The different 3'-azidfo derivatives were reduced to 3'-amino compounds. All 3'-azido- and 3'-aminopyrimidine nucleosides were tested against herpes simplex virus, vaccinia and vesicular stomatitis virus and on murine L1210 cell growth. None of the substances exhibited significant activity.