74131-09-2Relevant academic research and scientific papers
Synthesis and antiviral properties of (E)-5-(2-bromovinyl)-2'-deoxycytidine-related compounds
Jones,Sayers,Walker,De Clercq
, p. 268 - 271 (2007/10/02)
Treatment of 3',5'-di-O-acetyl-(E)-5-(2-bromovinyl)-2'-deoxyuridine (2) with p-chlorophenyl phosphorodichloridate and 1,2,4-triazole gave 1-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-(E)-5-(2-brom vinyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (3). Reaction of 3 with ammonia gave (E)-5-(2-bromovinyl)-2'-deoxycytidine (1), the overall yield from 2 being 60%. A similar 4-(1,2,4-triazol-1-yl) derivative (4) was obtained from 3',5'-di-O-acetylthymidine by the use of phosphoryl chloride as the condensing agent. Treatment of thymidine with trimethylsilyl chloride and then with phosphoryl chloride and 1,2,4-triazole gave upon workup 1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-methyl-4(1,2,4-triazol-1-yl pyrimidin-2(1H)-one (5). (E)-5-(2-Bromovinyl)-2'-deoxyuridine (BVDU) when similarly treated gave the corresponding (E)-5-(2-bromovinyl) compound 7. A minor product formed in both cases was a 4-(1,2,4-triazol-1-yl) derivative in which the nucleoside 5'-hydroxyl group had been replaced by chlorine (6 and 8). Whereas compounds 4-6 and 8 did not exhibit a selective antiviral effect, compounds 1-3 and 7 proved almost as active as the reference compound BVDU. In particular, compound 7, the 4-triazolyl derivative of BVDU, would seem worth pursuing for its potential as an inhibitor of herpes simplex virus type 1 and varicella-zoster virus.
E-5-(2-Halogenovinyl)-2'-deoxycytidines
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, (2008/06/13)
The invention relates to E-5-(2-halogenovinyl)-2'-deoxycytidines, e.g. E-5-(bromovinyl)-2'-deoxycytidine and E-5-(2-iodovinyl)-2'-deoxycytidine. These substances are endowed with specific antiviral activities towards herpes simplex virus and with an extremely low toxicity which makes them useful in antiviral medicines and for treatment of virus diseases in man and animal. They may be synthesized by introduction of an E-5-(2-halogenovinyl) sidechain into 2'-deoxycytidine, or by condensation of a trialkylsilyl derivative of E-5-(2-halogenovinyl)-cytosine with a hydroxyl-protected reactive derivative of 2'-deoxy-D-erythro-pentofuranose.
