Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes

Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes Full article

Journal

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

Output data

Year: 2019, Volume: 55, Number: 1, Pages: 52-59 Pages count : 8 DOI: 10.1007/s10600-019-02613-x

Tags

diterpenoids; isopimaric acid; amino acids; 1,2,3-triazoles; cytotoxicity; XSA

Authors

Gromova M.A. ¹ , Kharitonov Yu.V. ¹ , Pokrovskii M.A. ² , Bagryanskaya I.Yu. ^1,2 , Pokrovskii A.G. ² , Shul'ts E.E. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Prosp Lavrenteva, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 1 Pirogova St, Novosibirsk 630090, Russia

The synthesis and properties of tricyclic diterpenoids containing a C-4 functionalized oxazole ring are reported. The reaction of 4-[5-(bromomethyl)oxazol-2-yl]-18-norisopimarane with sodium azide in the presence of hydrated copper sulfate and sodium ascorbate in DMF gave the corresponding azide, from which new diterpenoid derivatives containing a 1H-substituted 1,2,3-triazol-4-yl substituent were synthesized. Reduction of the azide produced the terpenoid 5-aminomethyloxazole. Reaction of 4-[5-(bromomethyl)oxazol-2-yl]-18-norisopimarane with methyl esters of amino acids in DMF in the presence of potash synthesized compounds with oxazole C-5 amino-acid substituents. Cytotoxicity of the new isopimaric acid derivatives gainst CEM-13, MT-4, U-937, MCF-7, and MDA-MB-231 human tumor cells was studied.

Gromova M.A. , Kharitonov Y.V. , Pokrovskii M.A. , Bagryanskaya I.Y. , Pokrovskii A.G. , Shul'ts E.E.
Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes
Chemistry of Natural Compounds. 2019. V.55. N1. P.52-59. DOI: 10.1007/s10600-019-02613-x WOS Scopus РИНЦ OpenAlex

Published print:	Jan 1, 2019
Published online:	Feb 21, 2019

Web of science:	WOS:000461554200013
Scopus:	2-s2.0-85063134864
Elibrary:	38672035
OpenAlex:	W2915512003

DB	Citing
Web of science	6
Scopus	8
Elibrary	9
OpenAlex	8