Synthetic Transformations of Higher Terpenoids. 43. Synthesis and Cytotoxic Properties of New Lambertianic Acid Derivatives at the Carboxylic Group

Synthetic Transformations of Higher Terpenoids. 43. Synthesis and Cytotoxic Properties of New Lambertianic Acid Derivatives at the Carboxylic Group Научная публикация

Журнал

Chemistry of Natural Compounds
ISSN: 0009-3130 , E-ISSN: 1573-8388

Вых. Данные

Год: 2023, Номер: 6, Страницы: 936–947 Страниц : DOI: 10.1007/s10600-023-04206-1

Ключевые слова

diterpenoids, lambertianic acid, amides, cytotoxicity

Авторы

Kharitonov Yu.V. ¹ , Antipova V.I. ¹ , Marenina M.K. ¹ , Meshkova Yu.V. ¹ , Tolstikova T.G. ¹ , Shults E.E. ¹

Организации

1	Новосибирский институт органической химии им. Н.Н. Ворожцова СО РАН

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 μM (selectivity index >7).

Kharitonov Y.V. , Antipova V.I. , Marenina M.K. , Meshkova Y.V. , Tolstikova T.G. , Shults E.E.
Synthetic Transformations of Higher Terpenoids. 43. Synthesis and Cytotoxic Properties of New Lambertianic Acid Derivatives at the Carboxylic Group
Chemistry of Natural Compounds. 2023. №6. С.936–947. DOI: 10.1007/s10600-023-04206-1 WOS РИНЦ

Поступила в редакцию:	14 мая 2023 г.
Опубликована в печати:	9 нояб. 2023 г.

Web of science	WOS:001101620600009
РИНЦ	65305473
OpenAlex	W4388524597