C5-Modified nucleosides exhibiting anticancer activity
Yoon-Suk Lee1, Sun Min Park, Hwan Mook Kim
1Department of Chemistry, BK School of Molecular Science, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea.
Abstract:
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.
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