91593-18-9

Upstream product

• 86163-17-9 methyl (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylate 
• 74131-06-9 (E)-3-(1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid 
• 108-24-7 acetic anhydride 
• 69304-47-8 (E)-5-(2-bromovinyl)-2'-deoxyuridine 
• 54-42-2 5-Iodo-2'-deoxyuridine 

Downstream Products

• 74131-09-2 (E)-5-(2-bromovinyl)-2'-deoxycytidine 
• 111160-27-1 1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-(E)-5-(2-bromovinyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one 

Relevant academic research and scientific papers

Synthesis and in vitro anti-mycobacterial activity of 5-substituted pyrimidine nucleosides

Mycobacterium tuberculosis and Mycobacterium avium infections cause the two most important mycobacterioses, leading to increased mortality in patients with AIDS. Various 5-substituted 2′-deoxyuridines, uridines, 2′-O-methyluridine, 2′-ribofluoro-2′-deoxyuridines, 3′-substituted-2′,3′-dideoxy uridines, 2′,3′- dideoxyuridines, and 2′,3′-didehydro-2′,3′- dideoxyuridines were synthesized and evaluated for their in vitro inhibitory activity against M. bovis and M. avium. 5-(C-1 Substituted)-2′- deoxyuridine derivatives emerged as potent inhibitors of M. avium (MIC 90 = 1-5 μg/mL range). The nature of C-5 substituents in the 2′-deoxyuridine series appeared to be a determinant of anti-mycobacterial activity. This new class of inhibitors could serve as useful compounds for the design and study of new anti-tuberculosis agents.

THE SYNTHESIS AND ANTIVIRAL PROPERTIES OF (E)-5-(2-BROMOVINYL)-2'-DEOXYURIDINE-RELATED COMPOUNDS

A method for the synthesis of the potent anti-herpes agent, (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) (1) is described.A trace bye-product of the synthesis has been identified as 5-(1,2-dibromo-2-succinimidoethyl)-2'-deoxyuridine (5).A similar bye-product, 5-(1,2-dibromo-2-succinimidoethyl)uridine (4) is formed during the synthesis of (E)-5-(2-bromovinyl)uridine (3).The following derivatives of BVDU have been synthesised: 3'-O-methyl (8), 3-methyl (9), 4-O-ethyl (11), O2,5'-anhydro-(E)-5-(2-bromovinyl)-2'-deoxyuridine (13) and (E)-5-(2-bromovinyl)-2'-deoxyisocytidine (15).Whereas compounds 8, 9 and 15 showed little, if any, antiviral activity, 11 and, in particular, 13, were significantly active against herpes simplex virus type 1 and varicella-zoster virus.