Synthetic Transformations of Higher Terpenoids. 44#. Synthesis of New Derivatives of 18-Nor-4-Amino-8(17),13,14-Labdatriene and Evaluation of Their Cytotoxicity for MCF7, HepG2, and HeLa Tumor Cell Lines

Synthetic Transformations of Higher Terpenoids. 44#. Synthesis of New Derivatives of 18-Nor-4-Amino-8(17),13,14-Labdatriene and Evaluation of Their Cytotoxicity for MCF7, HepG2, and HeLa Tumor Cell Lines Full article

Journal

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

Output data

Year: 2024, Volume: 60, Number: 2, Pages: 252-262 Pages count : 11 DOI: 10.1007/s10600-024-04299-2

Tags

diterpenoids lambertianic acid 18-norlabdanoids amines 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, Siberian Branch, Russian Academy of Sciences

Various N-containing 18-norlabdanoids were synthesized via reactions of 18-nor-4-amino-15,16-epoxy-8(17),13(16),14-labdatriene with methyl iodide, aromatic aldehydes, acetic and trifluoroacetic acid anhydrides, benzoyl chloride, sulfonyl chlorides, bromoacetic acid chloride, and methyl bromoacetate and condensation with azidobenzoic acids. The cytotoxic activity (MTT assay) against MCF7, HepG2, and HeLa tumor cell lines was shown to increase significantly if the lambertianic acid carboxylic group was replaced by an amine. Subsequent modification of the N-containing substituent by addition of an N′-substituted glycylamide moiety altered the cytotoxicity and selectivity. The synthesized compounds had the greatest effect on the viability of MCF7 cell line. The IC50 value for the most active compound was 8 μM.

Kharitonov Y.V. , Antipova V.I. , Marenina M.K. , Meshkova Y.V. , Tolstikova T.G. , Shults E.E.
Synthetic Transformations of Higher Terpenoids. 44#. Synthesis of New Derivatives of 18-Nor-4-Amino-8(17),13,14-Labdatriene and Evaluation of Their Cytotoxicity for MCF7, HepG2, and HeLa Tumor Cell Lines
Chemistry of Natural Compounds. 2024. V.60. N2. P.252-262. DOI: 10.1007/s10600-024-04299-2

Submitted:	Oct 9, 2023
Published print:	Mar 28, 2024

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