Targeted synthesis of macrodiolides containing bis-methylene-separated Z-double bonds and their antitumor activity in vitro
Тип публикации: Journal Article
Дата публикации: 2018-08-01
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
An original strategy has been developed for the synthesis of valuable unsaturated macrocyclic lactones, macrodiolides, containing a 1Z,5Z-diene moiety in 57–79% yields and >98% stereoselectivity by hafnium triflate Hf(OTf)4-catalyzed intermolecular esterification of aliphatic α,ω-dicarboxylic acids with α,ω-alka-nZ,(n+4)Z-dienediols (1,12-dodeca-4Z,8Z-dienediol, 1,14-tetradeca-5Z,9Z-dienediol, 1,18-octadeca-7Z,11Z-dienediol). The diols were obtained by homo-cyclomagnesiation of tetrahydropyran ethers of oxygenated 1,2-dienes with EtMgBr in the presence of Mg metal and Cp2TiCl2 catalyst (10 mol. %). The resulting macrodiolides exhibit high cytotoxic activity in vitro against Jurkat, K562, U937, Hek293 and HeLa tumor cell lines.
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D'yakonov V. A. et al. Targeted synthesis of macrodiolides containing bis-methylene-separated Z-double bonds and their antitumor activity in vitro // Tetrahedron. 2018. Vol. 74. No. 35. pp. 4606-4612.
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D'yakonov V. A., Islamov I. I., Dzhemileva L. U., Khusainova E. M., Yunusbaeva M. M., Dzhemilev U. M. Targeted synthesis of macrodiolides containing bis-methylene-separated Z-double bonds and their antitumor activity in vitro // Tetrahedron. 2018. Vol. 74. No. 35. pp. 4606-4612.
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TY - JOUR
DO - 10.1016/j.tet.2018.07.031
UR - https://doi.org/10.1016/j.tet.2018.07.031
TI - Targeted synthesis of macrodiolides containing bis-methylene-separated Z-double bonds and their antitumor activity in vitro
T2 - Tetrahedron
AU - D'yakonov, Vladimir A
AU - Islamov, Ilgiz I
AU - Dzhemileva, Lilya U.
AU - Khusainova, Elvina M
AU - Yunusbaeva, Milyausha M.
AU - Dzhemilev, Usein M
PY - 2018
DA - 2018/08/01
PB - Elsevier
SP - 4606-4612
IS - 35
VL - 74
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2018_D'yakonov,
author = {Vladimir A D'yakonov and Ilgiz I Islamov and Lilya U. Dzhemileva and Elvina M Khusainova and Milyausha M. Yunusbaeva and Usein M Dzhemilev},
title = {Targeted synthesis of macrodiolides containing bis-methylene-separated Z-double bonds and their antitumor activity in vitro},
journal = {Tetrahedron},
year = {2018},
volume = {74},
publisher = {Elsevier},
month = {aug},
url = {https://doi.org/10.1016/j.tet.2018.07.031},
number = {35},
pages = {4606--4612},
doi = {10.1016/j.tet.2018.07.031}
}
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MLA
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D'yakonov, Vladimir A., et al. “Targeted synthesis of macrodiolides containing bis-methylene-separated Z-double bonds and their antitumor activity in vitro.” Tetrahedron, vol. 74, no. 35, Aug. 2018, pp. 4606-4612. https://doi.org/10.1016/j.tet.2018.07.031.
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