C5-Modified nucleosides exhibiting anticancer activity.
We describe (i) a simple method for the synthesis of C5-modified nucleosides from 5-iodo-2'-deoxyuridine and (ii) their activity against six types of human cancer cell lines (HCT15, MM231, NCI-H23, NUGC-3, PC-3, ACHN). We generated nitrile oxides in situ from oximes using a commercial bleaching agent; their cycloadditions with 5-ethynyl-2'-deoxyuridine yielded isoxazole derivatives possessing activity against the cancer cell lines. We synthesized several azides from benzylic bromides and their click reactions with 5-ethynyl-2'-deoxyuridine provided triazole derivatives.
Lee
Yoon-Suk
YS
Department of Chemistry, BK School of Molecular Science, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea.
Park
Sun Min
SM
Kim
Hwan Mook
HM
Park
Song-Kyu
SK
Lee
Kiho
K
Lee
Chang Woo
CW
Kim
Byeang Hyean
BH
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007555:Isoxazoles / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000970:Antineoplastic Agents; D007555:Isoxazoles; D009705:Nucleosides; C031086:5-ethynyl-2'-deoxyuridine; D003857:Deoxyuridine