Radical deoxygenation of tert-alcohols in 2'-branched-chain sugar pyrimidine nucleosides: synthesis and antileukemic activity of 2'-deoxy-2' (S)-methylcytidine.
Тип публикации: Journal Article
Дата публикации: 2011-12-08
scimago Q3
wos Q3
БС2
SJR: 0.349
CiteScore: 2.7
Impact factor: 1.3
ISSN: 00092363, 13475223
PubMed ID:
3435995
General Chemistry
Drug Discovery
General Medicine
Краткое описание
We have synthesized 2'-deoxy-2' (S) -methylcytidine (7), a new antileukemic nucleoside. The carbonyl methylation of 2'-ketonucleoside (1) with MeLi, Me3Al 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 NH3 furnished 7. The structure-activity relationships of 7 and some other 2'-branched-chain sugar cytidines against L1210 cells are also described.
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Matsuda A. et al. Radical deoxygenation of tert-alcohols in 2'-branched-chain sugar pyrimidine nucleosides: synthesis and antileukemic activity of 2'-deoxy-2' (S)-methylcytidine. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 35. No. 9. pp. 3967-3970.
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Matsuda A., TAKENUKI K., ITOH H., Sasaki T., UEDA T. Radical deoxygenation of tert-alcohols in 2'-branched-chain sugar pyrimidine nucleosides: synthesis and antileukemic activity of 2'-deoxy-2' (S)-methylcytidine. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 35. No. 9. pp. 3967-3970.
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TY - JOUR
DO - 10.1248/cpb.35.3967
UR - https://doi.org/10.1248/cpb.35.3967
TI - Radical deoxygenation of tert-alcohols in 2'-branched-chain sugar pyrimidine nucleosides: synthesis and antileukemic activity of 2'-deoxy-2' (S)-methylcytidine.
T2 - Chemical and Pharmaceutical Bulletin
AU - Matsuda, Akira
AU - TAKENUKI, Kenji
AU - ITOH, Hiroko
AU - Sasaki, Takuma
AU - UEDA, Tohru
PY - 2011
DA - 2011/12/08
PB - Pharmaceutical Society of Japan
SP - 3967-3970
IS - 9
VL - 35
PMID - 3435995
SN - 0009-2363
SN - 1347-5223
ER -
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@article{2011_Matsuda,
author = {Akira Matsuda and Kenji TAKENUKI and Hiroko ITOH and Takuma Sasaki and Tohru UEDA},
title = {Radical deoxygenation of tert-alcohols in 2'-branched-chain sugar pyrimidine nucleosides: synthesis and antileukemic activity of 2'-deoxy-2' (S)-methylcytidine.},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2011},
volume = {35},
publisher = {Pharmaceutical Society of Japan},
month = {dec},
url = {https://doi.org/10.1248/cpb.35.3967},
number = {9},
pages = {3967--3970},
doi = {10.1248/cpb.35.3967}
}
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MLA
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Matsuda, Akira, et al. “Radical deoxygenation of tert-alcohols in 2'-branched-chain sugar pyrimidine nucleosides: synthesis and antileukemic activity of 2'-deoxy-2' (S)-methylcytidine..” Chemical and Pharmaceutical Bulletin, vol. 35, no. 9, Dec. 2011, pp. 3967-3970. https://doi.org/10.1248/cpb.35.3967.