RADICAL DEOXYGENATION OF TERT-ALCOHLS IN 2'-BRANCHED-CHAIN SUGAR PYRIMIDINE NUCLEOSTDES : SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF 2'-DEOXY-2'(S)-METHYLCYTIDINE(Communications to the Editor)
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概要
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We have synthesized 2'-deoxy-2'(S)-methylcytidine (7), a new antileukemic nucleoside. The carbonyl methylation of 2'-ketonucleoside (1) with MeLi, Me_3Al and MeMgX was examined. Only in the reaction with MeMgX, did the more hindered β-attack afford the 2'-methyl-t-alcohol (2b). Compound 2b was converted into the methyl oxalate (4), which was subjected to radical deoxygenation to give the 2'-deoxy-2'(S)-methyl derivative (5). The deprotection of 5 followed by substitution with NH_3 furnished 7. Tne structure-activity relationships of 7 and some other 2'-branched-chain sugar cytidines against L1210 cells are also described.
- 公益社団法人日本薬学会の論文
- 1987-09-25
著者
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Matsuda A
Hokkaido Univ. Sapporo Jpn
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MATSUDA Akira
Faculty of Pharmaceutical Sciences, Hokkaido University
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SASAKI Takuma
Cancer Research Institute, Kanazawa University
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UEDA TOHRU
Faculty of Pharmaceutical Sciences, Hokkaido University
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Itoh Hiroko
Faculty Of Pharmaceutical Sciences Hokkaido University
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Sasaki T
Daiichi Seiyaku Co. Ltd. Tokyo Jpn
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Sasaki Takuma
Cancer Research Institute Kanazawa University
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Takenuki Kenji
Faculty of Pharmaceutical Sciences, Hokkaido University
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Takenuki K
Hokkaido Univ. Sapporo Jpn
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Matsuda Akira
Faculty Of Pharmaceutical Sciences Hokkaido University
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Ueda Tohru
Faculty Of Bioresource Sciences Akita Prefectural University
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