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

Author:
Gromova, M. A., Kharitonov, Y.u V., Pokrovskii, M. A., Bagryanskaya, I. Yu., Pokrovskii, A. G., Shul’ts, E. E.
Source:
Chemistry of natural compounds 2019 v.55 no.1 pp. 52-59
ISSN:
0009-3130
Subject:
amino acids, ascorbic acid, chemistry, copper, copper sulfate, cytotoxicity, diterpenoids, esters, humans, neoplasm cells, oxazoles, sodium azide
Abstract:
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.
Agid:
6332308