3052-06-0

Usage

InChI:InChI=1/C9H11IN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6+,8-/m1/s1

Upstream product

• 3083-77-0 araU 
• 14057-18-2 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil 
• 58-96-8 uridine 
• 3736-77-4 2,2'-Anhydrouridine 
• 84500-33-4 1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)-5-iodo-pyrimidine-2,4(3H)-dione 
• 1024-99-3 5-iodouridine 

Downstream Products

• 69075-42-9 5-ethynyluridine 
• 73556-52-2 5'-O-trityl-6,2'-O-cyclouridine 
• 73556-50-0 5-iodo-5'-O-trityl-1-(β-D-arabinofuranosyl)uracil 

Relevant academic research and scientific papers

Synthesis and evaluation of 5-substituted 2′-deoxyuridine monophosphate analogues as inhibitors of flavin-dependent thymidylate synthase in mycobacterium tuberculosis

A series of 5-substituted 2′-deoxyuridine monophosphate analogues has been synthesized and evaluated as potential inhibitors of mycobacterial ThyX, a novel flavin-dependent thymidylate synthase in Mycobacterium tuberculosis. A systematic SAR study led to the identification of compound 5a, displaying an IC50 value against mycobacterial ThyX of 0.91 μM. This derivative lacks activity against the classical mycobacterial thymidylate synthase ThyA (IC50 > 50 μM) and represents the first example of a selective mycobacterial FDTS inhibitor.

Synthesis of 5-radioiodoarabinosyl uridine analog for probing the HSV-1 thymidine kinase gene

Tumor cells transduced with herpes simplex virus thymidine kinase gene have been intensively applied to the field of positron emission tomography via imaging of its substrate. As a pilot synthesis approach, a facile preparation of 5-[125I]iodoarabinosyl uridine starting from commercially available uridine is reported herein.

Treatment of EBV and KHSV infection and associated abnormal cellular proliferation

A method and composition for the treatment, prevention and/or prophylaxis of a host, and in particular, a human, infected with Epstein-Barr virus (EBV), is provided that includes administering an effective amount of a 5-substituted uracil nucleoside or its pharmaceutically acceptable salt or prodrug, optionally in a pharmaceutically acceptable diluent or excipient.

Anti-HCV nucleoside derivatives

The present invention comprises novel and known purine and pyrimidine nucleoside derivatives which have been discovered to be active against hepatitis C virus (HCV). The use of these derivatives for the treatment of HCV infection is claimed as are the novel nucleoside derivatives disclosed herein.

A mild and efficient methodology for the synthesis of 5-halogeno uracil nucleosides that occurs via a 5-halogeno-6-azido-5,6-dihydro intermediate

A mild and efficient methodology for the synthesis of 5-halogeno (iodo, bromo, or chloro) uracil nucleosides has been developed. 5-Halo-2'-deoxyuridines 4a-c (84-95%), 5-halouridines 7a-c (45-95%), and 5-haloarabinouridines 8a-c (65-95%) were synthesized in good to excellent yields by the reaction of 2'-deoxyuridine (2), uridine (5) and arabinouridine (6), respectively with iodine monochloride, or N-bromo (or chloro)succinimide, and sodium azide at 25-45°C. These C-5 halogenation reactions proceed via a 5-halo-6-azido-5,6-dihydro intermediate (3), from which HN3 is eliminated, to yield the 5-halogeno uracil nucleoside. The 5-halo-6-azido-5,6-dihydro intermediate products (10a, 10b) could be isolated from the reaction of 3',5'-di-O-acetyl-2'-deoxyuridine (9) with iodine monochloride or N-bromosuccinimide and sodium azide at 0°C. The isolation of 10a, 10b indicates that the C-5 halogenation reaction proceeds via a 5-halo-6-azido-5,6-dihydro intermediate.

Antiviral compounds

The present invention relates to certain novel 5-substituted pyrimidine nucleosides and pharmaceutically acceptable derivatives thereof and their use in the treatment of varicella zoster virus, cytomegalovirus and Epstein Barr virus infections. Also provided are pharmaceutical formulations and processes for the preparation of the compounds according to the invention.

Process for the preparation of pyrimidine nucleosides

A process is provided for the preparation of a compound of formula (I) or a salt thereof: wherein R1 is hydrogen or a C1 4 alkyl, comprising reacting a compound of formula II: with an agent serving to introduce the alkynyl radical of formula -C≡CR1 (wherein R1 is as described above) at the 5-position of the pyrimidine base, the reaction being carried out in the presence of an N1 6 alkylmorpholine, wherein said alkyl moiety being optionally substituted by an alkoxy or halogen group; and optionally thereafter converting into a salt.

1-(β-D-arabinofuranosyl)-5-propynyluracil for treatment of VZV infections

The invention is a method for using 1-(β-D-arabinofuranosyl)-5-propynyluracil or its salts as the active ingredient in pharmaceutical compositions in the treatment of varicella zoster viral infections whether expressed as chicken pox or shingles.

Anti-HBV pyrimidine nucleoside

This invention relates to 1-(β-D-Arabinofuranosyl)5-prop-1-ynyluracil and pharmaceutically acceptable derivatives thereof for use in the treatment of hepatitis viral infections, particularly hepatitis B viral infections.