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

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

Journal

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

Output data

Year: 2023, Volume: 59, Number: 1, Pages: 87-93 Pages count : 7 DOI: 10.1007/s10600-023-03924-w

Tags

steroidal alkaloids, solasodine, acetylene, Mannich reaction, cytotoxicity

Authors

Finke A.O. ¹ , Mironov M.E. ^1,2 , Pokrovskii M.A. ² , Shults E.E. ¹

Affiliations

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

The reaction of the steroidal alkaloid solasodine with formaldehyde, terminal arylalkynes, 2-ethynylpyridine, propiolic acid methyl ester, or (trimethylsilyl)acetylene with heating to 100°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.

Finke A.O. , Mironov M.E. , Pokrovskii M.A. , Shults E.E.
Mannich Reaction of Solasodine with Acetylenes and Formaldehyde. Cytotoxicity of N-Propargyl-Substituted Alkaloid Derivatives
Chemistry of Natural Compounds. 2023. V.59. N1. P.87-93. DOI: 10.1007/s10600-023-03924-w WOS РИНЦ

Submitted:	Jun 10, 2022
Published print:	Feb 28, 2023

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