96253-17-7

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 96253-10-0 1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione 
• 58-96-8 uridine 

Downstream Products

• 6206-18-4 1-(3'-Brom-3'-desoxy-β-D-arabinofuranosyl)-uracil 

Relevant academic research and scientific papers

3′-Bromo analogues of pyrimidine nucleosides as a new class of potent inhibitors of mycobacterium tuberculosis

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.

NOVEL NUCLEOSIDE ANALOGUES VIA DIRECT ATTACK OF CARBON NUCLEOPHILES ON NUCLEOSIDES CONTAINING EPOXY-SUGARS

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.