Mannich Reaction of Solasodine with Acetylenes and Formaldehyde. Cytotoxicity of N-Propargyl-Substituted Alkaloid Derivatives

Chemistry of Natural Compounds
2023.0

Abstract

The reaction of the steroidal alkaloid solasodine with formaldehyde, terminal arylalkynes, 2-ethynylpyridine, propiolic acid methyl ester, or (trimethylsilyl)acetylene with heating to 100 degrees C in 1,4-dioxane in the presence of CuI synthesized the corresponding N-(prop-2-ynyl)spiro solanes as mixtures of (22R,25R)- and (22S,25R)-diastereomers in 28-81% yields and 1.6-1:1-1.7 ratios of stereoisomers. The cytotoxicities of the new solasodine derivatives against T98G, U-87, MT-4, and MDA-MB-231 human tumor cells were tested in vitro.

Knowledge Graph

Similar Paper