Synthesis and antitumor activity of 1-beta-4-selenoarabinofuranosyl cytosine (4'-seleno-ara-C).
4-Seleno analogue of 1-beta-arabinofuranosyl cytosine (ara-C) was synthesized via 4'-selenouridine as a key intermediate, which was easily prepared from D-ribose. The arabino configuration was achieved by chemoselective ring opening of the 2,2'-anhydro-4'-selenouridine. The synthesized 4'-seleno-ara-C showed potent antitumor activity (IC(50) = 1.5 microM) against stomach cancer cells (SNU638).
Lee
Hankil
H
Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, Korea.
Tosh
Dilip K
DK
Choi
Won Jun
WJ
Kim
Yu Min
YM
Lee
Sang Kook
SK
Jeong
Lak Shin
LS
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D003561:Cytarabine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014529:Uridine / Q000031:analogs & derivatives / Q000737:chemistry
C541636:1-beta-4-selenoarabinofuranosyl cytosine; C528350:4'-selenouridine; D000970:Antineoplastic Agents; D016566:Organoselenium Compounds; D003561:Cytarabine; D014529:Uridine