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

[1] Synthetic Transformations of Higher Terpenoids. 43. Synthesis and Cytotoxic Properties of New Lambertianic Acid Derivatives at the Carboxylic Group
Yu.V. Kharitonov
V. I. Antipova
M. K. Marenina
Yu.V. Meshkova
T. G. Tolstikova
E. E. Shults
Chemistry of Natural Compounds, 2023, 59 : 1109 - 1121
[2] Synthetic Transformations of Higher Terpenoids. XXXV.* Synthesis and Cytotoxicity of Macroheterocyclic Compounds Based on Lambertianic Acid
Yu. V. Kharitonov
M. M. Shakirov
M. A. Pokrovskii
A. G. Pokrovskii
E. E. Shul’ts
Chemistry of Natural Compounds, 2017, 53 : 77 - 82
[3] Synthetic Transformations of Higher Terpenoids. XXXV. Synthesis and Cytotoxicity of Macroheterocyclic Compounds Based on Lambertianic Acid
Kharitonov, Yu. V.
Shakirov, M. M.
Pokrovskii, M. A.
Pokrovskii, A. G.
Shul'ts, E. E.
CHEMISTRY OF NATURAL COMPOUNDS, 2017, 53 (01) : 77 - 82
[4] Synthetic Transformations of Higher Terpenoids. 40. Synthesis and Assessment of Analgesic Activity of N-Containing Derivatives of Lambertianic Acid
Yu. V. Kharitonov
E. E. Shul’ts
T. V. Rybalova
A. V. Pavlova
T. G. Tolstikova
Chemistry of Natural Compounds, 2021, 57 : 879 - 886
[5] Synthetic Transformations of Higher Terpenoids. 40. Synthesis and Assessment of Analgesic Activity of N-Containing Derivatives of Lambertianic Acid
Kharitonov, Yu. V.
Shul'ts, E. E.
Rybalova, T. V.
Pavlova, A. V.
Tolstikova, T. G.
CHEMISTRY OF NATURAL COMPOUNDS, 2021, 57 (05) : 879 - 886
[6] Synthetic Transformations of Higher Terpenoids. 39.* Synthesis and Analgesic Activity of Isopimaric Acid Derivatives
Gromova, M. A.
Kharitonov, Yu. V.
Borisov, S. A.
Baev, D. S.
Tolstikova, T. G.
Shul'ts, E. E.
CHEMISTRY OF NATURAL COMPOUNDS, 2021, 57 (03) : 474 - 481
[7] Synthetic Transformations of Higher Terpenoids. 39.∗ Synthesis and Analgesic Activity of Isopimaric Acid Derivatives
M. A. Gromova
Yu. V. Kharitonov
S. A. Borisov
D. S. Baev
T. G. Tolstikova
E. E. Shul’ts
Chemistry of Natural Compounds, 2021, 57 : 474 - 481
[8] Synthetic transformations of higher terpenoids. XXI.* preparation of phlomisoic acid and its N-containing derivatives
Mironov M.E.
Kharitonov Y.V.
Shul'ts E.E.
Shakirov M.M.
Bagryanskaya Y.
Tolstikov G.A.
Chemistry of Natural Compounds, 2010, 46 (2) : 233 - 241
[9] SYNTHETIC TRANSFORMATIONS OF HIGHER TERPENOIDS. XXI. PREPARATION OF PHLOMISOIC ACID AND ITS N-CONTAINING DERIVATIVES
Mironov, M. E.
Kharitonov, Yu. V.
Shul'ts, E. E.
Shakirov, M. M.
Bagryanskaya, I. Yu.
Tolstikov, G. A.
CHEMISTRY OF NATURAL COMPOUNDS, 2010, 46 (02) : 233 - 241
[10] Synthetic transformations of higher terpenoids. XXVII.* Synthesis of 7-hydroxylabdanoids and their transformations
Kharitonov, Yu V.
Shul'ts, E. E.
Gatilov, Yu V.
Bagryanskaya, I. Yu
Shakirov, M. M.
Tolstikov, G. A.
CHEMISTRY OF NATURAL COMPOUNDS, 2012, 48 (02) : 250 - 257

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