De novo synthesis of two new cytotoxic tiazofurin analogues with modified sugar moieties

• Published in: Bioorganic & medicinal chemistry letters Vol. 13; no. 19; pp. 3167 - 3170
• Main Authors: Popsavin, Mirjana, Torović, Ljilja, Kojić, Vesna, Bogdanović, Gordana, Spaić, Saša, Popsavin, Velimir
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 06.10.2003; Elsevier
• Subjects: Antineoplastic agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - toxicity; Biological and medical sciences; Cell Line; Cell Line, Tumor; General aspects; Glucose - chemical synthesis; Glucose - toxicity; Humans; Medical sciences; Pharmacology. Drug treatments; Ribavirin - analogs & derivatives; Ribavirin - chemical synthesis; Ribavirin - toxicity; Antineoplastic agent; Human; Sulfur nitrogen heterocycle; Solid tumor; C-Nucleoside; Five membered ring; Leukemia; Thiazole derivatives; Cytotoxicity; In vitro; Biological activity; Tiazofurine; Cell line; Fetus; Fluorine Organic compounds; Colon; Mammary gland; Chemical synthesis; Tumor cell
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(03)00712-1

A divergent synthesis of two novel tiazofurin analogues, 2-(3-deoxy-3-fluoro-β- d-xylofuranosyl)thiazole-4-carboxamide ( 2) and 2-(3-acetamido-3-deoxy-β- d-xylofuranosyl)thiazole-4-carboxamide ( 3), has been achieved starting from d-glucose. Both nucleoside analogues were evaluated for their in vitro cytotoxicity against several human leukaemia and solid tumour cell lines. A multistep divergent synthesis of two new cytotoxic tiazofurin analogues 2 and 3 has been achieved starting from d-glucose.