84472-84-4

Usage

InChI:InChI=1/C28H25N5O4/c29-32-31-23-18-26(33-17-16-25(34)30-27(33)35)37-24(23)19-36-28(20-10-4-1-5-11-20,21-12-6-2-7-13-21)22-14-8-3-9-15-22/h1-17,23-24,26,29H,18-19H2/p+1

Upstream product

• 5964-40-9 2,3'-anhydro-1-(2,3-dideoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil 
• 76-83-5 trityl chloride 
• 951-78-0 2'-deoxyuridine 
• 84472-83-3 1-[2-deoxy-5-O-(triphenylmethyl)-β-D-xylofuranosyl]uracil 
• 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

• 859206-78-3 3'-amino-5'-O-trityl-2',3'-dideoxyuridine 
• 859206-79-4 3'-acetylamino-5'-O-trityl-2',3'-dideoxyuridine 
• 84472-87-7 3'-azido-2',3'-dideoxy-5'-O-acetyluridine 
• 84472-89-9 3'-azido-2',3'-dideoxycytidine 
• 84472-90-2 3'-amino-2',3'-dideoxycytidine 
• 84472-86-6 3'-amino-2',3'-dideoxyuridine 
• 127492-39-1 1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-chloro-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

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.

Chemical-enzymatic synthesis of 3'-amino-2',3'-dideoxy-β-D- ribofuranosides of natural heterocyclic bases and their 5'-monophosphates

Treatment of O2,3'-anhydro-5'-O-trityl derivatives of thymidine (1) and 2'-deoxyuridine (2) with lithium azide in dimethylformamide at 150 °C resulted in the formation of the corresponding isomeric 3'-azido-2',3'- dideoxy-5'-O-trityl-β-D-ribofuranosyl N1- (the major products) and N3- nucleosides 3/4 and 5/6). 3'-Amino-2',3'-dideoxy-β-D-ribofuranosides of thymidine [Thd(3'NH2)], uridine [dUrd(3'NH2)], and cytidine [dCyd(3'NH2)] were synthesized from the corresponding 3'-azido derivatives. The Thd(3'NH2) and dUrd(3'NH2) were used as donors of carbohydrate moiety in the reaction of enzymatic transglycosylation of adenine and guanine to afford dAdo(3'NH2) and dGuo(3'NH2). The substrate activity of dN(3'NH2) vs. nucleoside phosphotransferase of the whole cells of Erwinia herbicola was studied.

5'-Diphosphohexose nucleoside pharmaceutical compositions

Compounds of the general formula: STR1 wherein A, B, and C are hydrogen, halogen, or azido; D is hydrogen, halogen, azido, or OH; A and B or C and D can be replaced with a double bond; R is an aldohexose, aldohexosamine, or N-acetyl aldohexosamine, R

5'-diphosphohexose nucleoside pharmaceutical compositions

This invention provides compounds and pharmaceutical compositions that include compounds of the formula: STR1 in which A, B, and C are hydrogen, halogen, or azido; D is hydrogen, halogen, azido, or OH; A and B or C and D can be replaced with a double bond

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.

Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside

Several new 3'-azido and 3'-amino nucleosides (8, 9, 12, and 13) have been synthesized and their biological activities evaluated. Among them, 3'-amino-2',3'-dideoxycytidine (13) was found to exhibit potent cytotoxic activity against both L1210 and S-180 cells in vitro with an ID50 of 0.7 and 4.0 μM, respectively. Furthermore, 13 has also shown antitumor activity against L1210 tumor bearing mice with a T/C x 100 value of 283.