Synthesis of C-glycosyl thiazoles

The Chemistry of C-Nucleosides

“…3), was synthesized from 2,3,5-tri-Obenzoyl-p-D-ribofuranosyl cyanide (vide infra 89, Scheme 22) independently in two laboratories. (64,65) Tiazofurin was later found to exhibit potent activity against various murine and human tumors, (64,66--69) and is presently being evaluated in Phase 1 (70,71) and Phase II (72,73) clinical trials.…”

“…(64) A similar reaction of 231 with ethyl bromopyruvate in refiuxing ethanol gave 232 in 55% yield. (65) Ammonolysis of 232 afforded tiazofurin 235 in high yield. (64,65) An isomeric thiazole C-nucleoside 238 was also prepared from 231 by treatment with methyl chloroformylace tate, followed by ammonolysis of the product.…”

Synthesis and In‐vitro Activity of 4′‐Modified Analogues of ddA as Potent Anti‐HIV Agents

“…C-Nucleosides have received considerable attention due not only to the chemical stability but also to the interesting biological activities of naturally occurring compounds such as pseudoisocytidine [14], thiazofurin [15,16], and 9-deaza-adenosine [17,18] which have been reported. Only a few examples of synthetic C-nucleosides have been made, probably due to the synthetic difficulties of these nucleosides [19,20].…”

Synthesis of carbocyclic nucleoside analogs with five-membered heterocyclic nucleobases

“…Tiazofurin (1,2-(β- d -ribofuranosyl) thiazole-4-carboxamide, 3 , a synthetic C -nucleoside derivative, displayed potent anticancer activity. 15 An early discovery compound, 1,2,3-triazole carbocyclic nucleoside 4 16 , exhibited antiviral activity versus vaccinia virus. With these five-membered heterocyclic nucleobase containing nucleoside analogs as a backdrop, we designed novel carbocyclic nucleoside analogs as potential antiviral agents.…”