Regio- and Stereoselective Synthesis of 2′-Deoxy-4′-thioguanine Nucleosides: Evaluation of Anti-Hepatitis B Virus Activity and Cytotoxicity Leading to Improved Selectivity Index by 4′- C -Cyanation

• Published in: Synlett Vol. 35; no. 6; pp. 728 - 733
• Main Authors: Kumamoto, Hiroki, Imoto, Shuhei, Kuwata-Higashi, Nobuyo, Mitsuya, Hiroaki, Haraguchi, Kazuhiro
• Format: Journal Article
• Language: English; Japanese
• Published: STUTTGART Thieme Medical Publishers 05.12.2023
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; nucleosides; POTENT; ANALOGS; hepatitis B virus; deoxythioguanosine; glycals; medicinal chemistry; cytotoxicity

An N9-regio-and beta-anomer-selective 4 '-thioglycosidation of purine bases has been developed. The reaction between a 2-deoxy-2iodo-4-thioribofuranosyl glycosyl donor and N-(6-chloro-9H-purin-2-yl)-2-methylpropanamide gave the corresponding 2 '-deoxy-4 '-thiopu-rine nucleoside in 87%...