Synthesis and antiviral activity of novel exomethylene cyclopropyl pyrimidine nucleosides.
A series of novel exomethylene cyclopropyl nucleosides have been synthesized starting from Feist's acid. Classical nucleophilic substitution conditions (K2CO3, 18-crown-6) of the tosylate 2 as well as Mitsunobu reaction (DEAD, PPh3) of alcohol 1 with pyrimidine bases afforded a series of novel cyclopropyl nucleosides. Compound 4b displayed moderate anti-HBV activity without any cytotoxicity up to 100 microM.
Kook
Min Chul
MC
Department of Medicinal Chemistry, College of Pharmacy, Chonnam National University, Kwangju 500-757, Republic of Korea.
Kim
Gu
G
Kwak
Eun Yee
EY
Hong
Joon Hee
JH
Lee
Chong Kyo
CK
Choi
Bo Gil
BG
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D006838:Hydrocarbons; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D006571:Heterocyclic Compounds; D006838:Hydrocarbons; D011741:Pyrimidine Nucleosides; C030011:carbene; D008697:Methane