Synthesis and antiviral evaluation of (+/-)-4'-ethynyl-5'-difluorocarbocyclic-d4T analogue.
Synthesis of (+/-)-4'-ethynyl-5'-difluorocarbocyclic-d4T analogue 8, in which the furanose ring oxygen of usual nucleosides is replaced with a geminal-difluoromethylidene group, was carried out. Electrophilic fluorination with Selectfluor was applied to construct a gem-difluorocyclopentenone system to give 12. Regioselective introduction of thymine base was performed under the Mitsunobu conditions by employing the 4-methoxycarbonyl derivative 13. Antiviral evaluation of 8 was also examined.
Kumamoto
Hiroki
H
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. kumamoto@pharm.showa-u.ac.jp
Haraguchi
Kazuhiro
K
Ida
Mayumi
M
Tanaka
Hiromichi
H
Hamasaki
Takayuki
T
Baba
Masanori
M
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000998:Antiviral Agents; D003517:Cyclopentanes; D013936:Thymidine