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 Full article

Journal

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

Output data

Year: 2023, Number: 6, Pages: 936–947 Pages count : DOI: 10.1007/s10600-023-04206-1

Tags

diterpenoids, lambertianic acid, amides, cytotoxicity

Authors

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

Affiliations

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences

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

Submitted:	May 14, 2023
Published print:	Nov 9, 2023

Web of science	WOS:001101620600009
Elibrary	65305473
OpenAlex	W4388524597