96253-10-0Relevant academic research and scientific papers
Synthesis of 3′-azido-4′-ethynyl-3′,5′-dideoxy- 5′-norarabinouridine: A new anti-HIV nucleoside analogue
Amin, Mahmoud A.
, p. 1703 - 1708 (2011/04/18)
3′-Azido-4′-ethynyl-3′,5′dideoxy-5′- norarabinouridine 10 was synthesized from commercial uridine 1 in which the key step is the opening of protected 2′,3′-epoxyuridine derivative 7 by sodium azide and the hydroxymethyl at 4-position of the ribose ring are replaced by ethynyl group.
3′-Bromo analogues of pyrimidine nucleosides as a new class of potent inhibitors of mycobacterium tuberculosis
Shakya, Neeraj,Srivastav, Naveen C.,Desroches, Nancy,Agrawal, Babita,Kunimoto, Dennis Y.,Kumar, Rakesh
experimental part, p. 4130 - 4140 (2010/09/04)
Tuberculosis (TB) is a major health problem worldwide. We herein report a new class of pyrimidine nucleosides as potent inhibitors of Mycobacterium tuberculosis (M. tuberculosis). Various 2′- or 3′-halogeno derivatives of pyrimidine nucleosides containing uracil, 5-fluorouracil, and thymine bases were synthesized and evaluated for antimycobacterial activities. Among the compounds tested, 3′-bromo-3′-deoxy- arabinofuranosylthymine (33) was the most effective antituberculosis agent in the in vitro assays against wild-type M. tuberculosis strain (H37Ra) (MIC 50 = 1 μg/mL) as well as drug-resistant (H37Rv) (rifampicin-resistant and isoniazid-resistant) strains of M. tuberculosis (MIC50 = 1-2 μg/mL). Compound 33 also inhibited intracellular M. tuberculosis in a human monocytic cell line infected with H37Ra, demonstrating higher activity against intramacrophagic mycobacteria (80% reduction at 10 μg/mL concentration) than extracellular mycobacteria (75% reduction at 10 μg/mL concentration). In contrast, pyrimidine nucleosides possessing 5-fluorouracil base were weak inhibitors of M. tuberculosis. No cytotoxicity was found up to the highest concentration of compounds tested (CC50 > 100-200 μg/mL) against a human cell line. Overall, these encouraging results substantiate the potential of this new class of compounds as promising antituberculosis agents.
Preparation and cleavage reactions of 3′-thiouridylyl-(3′→5′)-uridine
Liu, Xiaohai,Reese, Colin B.
, p. 2227 - 2236 (2007/10/03)
3′-Thiouridylyl-(3′→5′)-uridine [(Us)pU] 3 is prepared by coupling together the disulfide 14 and the 5′-H-phosphonate 18, and then removing the protecting groups. (Us)pU 3 readily undergoes cleavage in 0.05 mol dm-3 sodium glycinate buffer (pH 10.06) at 50 °C to give, in the first instance, uridine 4 and 3′-thiouridine 2′,3′-cyclic phosphorothioate 21; in glacial acetic acid at 30 °C, it rapidly undergoes cleavage in essentially the same way. The behaviour of (Us)pU 3 is compared with that of uridylyl-(3′→5′)-uridine (UPU) 1a under the same basic and acidic reaction conditions. (Us)pU 3 and 3′-thiouridine 2′,3′-cyclic phosphorothioate 21 are both substrates for ribonuclease A; (Us)pU 3 is a substrate for Crotalus adamanteus snake venom phosphodiesterase but not for calf spleen phosphodiesterase.
Synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine; A unique antiviral nucleoside
Faul, Margaret M.,Huff, Bret E.,Dunlap, Steven E.,Frank, Scott A.,Fritz, James E.,Kaldor, Stephen W.,LeTourneau, Michael E.,Staszak, Michael A.,Ward, Jeffrey A.,Werner, John A.,Winneroski, Leonard L.
, p. 8085 - 8104 (2007/10/03)
The synthesis of 2',3'-dideoxy-3'-hydroxymethylcytidine 1 was accomplished using two different approaches. First, uridine and cytidine were used to prepare the key intermediate epoxides 15 and 31 which were opened with cyanide, deoxygenated by elimination to vinyl nitriles 17 and 36, and reduced by 1,4 hydride addition to the saturated nitriles 18 and 37. Secondly, a novel Rh-catalyzed hydroformylation reaction of 2',3'-didehydro-2',3'-dideoxycytidine 46 was used to prepare 1 in four steps. The attempted use of 2'-deoxyuridine and 2'-deoxycytidine to prepare 1 is also discussed.
Synthesis of 2',3'-Dithiouridine
Johnson, Richard,Joshi, Bhalchandra V.,Reese, Colin B.
, p. 133 - 134 (2007/10/02)
The synthesis of 2',3'-dithiouridine 2, starting from uridine, is described.
Azide- Or fluorine-containing 2′ & 3′-azolyluridines by regioselective opening of 1-(2′,3′-anhydro-β-d-lyxofuranosyl)uracils
Ariza, Xavier,Garces, Josep,Vilarrasa, Jaume
, p. 4069 - 4072 (2007/10/02)
Azide- or fluorine-containing imidazol-1-yl, pyrazol-1-yl, and 1,2,4-triazol-1-yl 2′,3′-dideoxyuridines have been synthesized from uridine in 5-6 steps, via 2′,3′-β-cpoxy ? derivatives. Regioselective oxirane-ring openings have been accomplished by appropriate choice of the reactions conditions.
NOVEL NUCLEOSIDE ANALOGUES VIA DIRECT ATTACK OF CARBON NUCLEOPHILES ON NUCLEOSIDES CONTAINING EPOXY-SUGARS
Mete, A.,Hobbs, J. B.
, p. 97 - 100 (2007/10/02)
Direct ring-opening of the epoxyde ring in 1-(5'-O-tityl-2',3'-anhydro-β-D-lyxofuranosyl) uracil(1) by lithium acetylide or vinylmagnesium bromide/cuprous iodide affords the corresponding 5'-O-trityl-3'-C-substituted-3'-deoxy-ara-uridine species.
