SYNTHETIC TRANSFORMATIONS OF HIGHER TERPENOIDS. 43.* SYNTHESIS AND CYTOTOXIC PROPERTIES OF NEW LAMBERTIANIC ACID DERIVATIVES AT THE CARBOXYLIC GROUP

被引：3

作者：

Kharitonov, Yu. V. ^{[1
]}

Antipova, V. I. ^{[1
]}

Marenina, M. K. ^{[1
]}

Meshkova, Yu. V. ^{[1
]}

Tolstikova, T. G. ^{[1
]}

Shults, E. E. ^{[1
]}

机构：

[1] Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Prosp Lavrenteva, Novosibirsk 630090, Russia

来源：

CHEMISTRY OF NATURAL COMPOUNDS | 2023年 / 59卷 / 06期

基金：

俄罗斯基础研究基金会;

关键词：

diterpenoids; lambertianic acid; amides; cytotoxicity; PLANTS;

D O I：

10.1007/s10600-023-04206-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Lambertianic acid was selectively transformed at the carboxylic group. Synthetic methods for natural labdanoids, i.e., lambertianic acid methyl ester and lambertianol, were proposed. New N-containing diterpenoid derivatives with alkyl(aryl)amide, dialkylamide, hydrazide, N-hydroxycarbamoyl, and nitrile groups in the C-4 position of the labdane skeleton were synthesized via reactions of lambertianic acid chloride with aliphatic and aromatic amines, amino acids, hydrazine, and hydroxylamine. Compounds with higher cytotoxicity than lambertianic acid against MCF-7, HeLa, and HepG2 (MTT assay) human tumor cell lines were obtained. The IC50 value of the most active lambertianic acid N-hydroxycarbamoyl derivative was 15 mu M (selectivity index >7).

引用

页码：1109 / 1121

页数：13

共 24 条

[21] Synthetic Transformations of Higher Terpenoids. 41. Synthesis and Anti-Inflammatory Activity of 4-(Carboxyalkyl)-18-nor-isopimara-7,15-Dienes
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Borisov, S. A.
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Shul'ts, E. E.
CHEMISTRY OF NATURAL COMPOUNDS, 2022, 58 (01) : 55 - 64
[22] Synthetic Transformations of Higher Terpenoids. 41. Synthesis and Anti-Inflammatory Activity of 4-(Carboxyalkyl)-18-nor-isopimara-7,15-Dienes
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Yu. V. Kharitonov
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[23] Synthetic transformations of higher triterpenoids. XXX. Synthesis and cytotoxic activity of betulonic acid amides with fragments of nitroxyl radicals
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E. E. Shults
Yu. F. Polienko
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[24] Synthetic transformations of higher triterpenoids. XXX. Synthesis and cytotoxic activity of betulonic acid amides with fragments of nitroxyl radicals
Antimonova, A. N.
Petrenko, N. I.
Shults, E. E.
Polienko, Yu F.
Shakirov, M. M.
Irtegova, I. G.
Pokrovskii, M. A.
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RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2013, 39 (02) : 181 - 185

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