85236-92-6

Basic information

• Product Name: 3'-azido-2',3'-dideoxy-5-iodouridine
• Synonyms: 3'-azido-2',3'-dideoxy-5-iodouridine
• CAS NO: 85236-92-6
• Molecular Formula: C₉H₁₀IN₅O₄
• Molecular Weight: 379.11127
• Mol File: 85236-92-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3'-azido-2',3'-dideoxy-5-iodouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-azido-2',3'-dideoxy-5-iodouridine(85236-92-6)
• EPA Substance Registry System: 3'-azido-2',3'-dideoxy-5-iodouridine(85236-92-6)

Safety Data

• Hazardous Substances Data: 85236-92-6(Hazardous Substances Data)

Upstream product

• 84472-85-5 Navuridine 
• 87190-83-8 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil 
• 85236-91-5 1-(3-chloro-2,3-dideoxy-β-D-threo-pentofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione 
• 54-42-2 5-Iodo-2'-deoxyuridine 
• 85236-90-4 1-<3-chloro-2,3-dideoxy-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl>-5-iodo-2,4(1H,3H)-pyrimidinedione 
• 15414-61-6 2'-deoxy-5-iodo-5'-O-(triphenylmethyl)uridine 
• 101039-85-4 2,3'-anydro-5-iodo-5'-O-trityl-2'-deoxyuridine 
• 101039-82-1 5-iodo-3'-O-mesyl-5'-O-trityl-2'-deoxyuridine 

Downstream Products

• 87190-83-8 1-(3-azido-2,3-dideoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-5-iodouracil 
• 120966-77-0 3'-azido-5'-O-(p-tolylsulfonyl)-2',3'-dideoxy-5-iodouridine 
• 120826-42-8 2,5'-anhydro-3'-azido-2',3'-dideoxy-5-iodouridine 
• 87190-89-4 1-((2R,4S,5S)-4-Azido-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione 

Relevant articles and documents

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 Biological Activity of Various 3'-Azido and 3'-Amino Analogues of 5-Substituted Pyrimidine Deoxyribonucleosides

Various new 5-substituted 3'-azido- and 3'-amino derivatives of 2'-deoxyuridine and 2'-deoxycytidine have been synthesized and biologically evaluated.Among these compounds, 3'-amino-2',3'-dideoxy-5-fluorouridine (3), 3'-amino-2',3'-dideoxycytidine (7a), and 3'-amino-2',3'-dideoxy-5-fluorocytidine (7c) were found to be the most active against murine L1210 and sarcoma 180 neoplastic cells in vitro, with an ED50 of 15 and 1 μM, 0.7 and 4 μM, and 10 and 1 μM, respectively.The 3'-azido derivatives, 2 and 6c, were less active in comparison with their 3'-amino counterparts.In addition, the 5-fluoro-3'-amino nucleosides, 3 and 7c, were tested against L1210 leukemia bearing CDF1 mice.Our preliminary findings indicate that compound 7c (6 * 200 mg/kg) was as active as the positive control, 5-fluorouracil (6 * 20 mg/kg), yielding a T/C * 100 of 146 and 129, respectively.However, 3 was found to be inactive in this experiment.