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

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Mannich Reaction of Solasodine with Acetylenes and Formaldehyde. Cytotoxicity of N-Propargyl-Substituted Alkaloid Derivatives. / Finke, A. O.; Mironov, M. E.; Pokrovskii, M. A. et al.

In: Chemistry of Natural Compounds, Vol. 59, No. 1, 01.2023, p. 87-93.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{b103f384d11547d299c068d70a133868,

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

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°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.",

keywords = "Mannich reaction, acetylene, cytotoxicity, solasodine, steroidal alkaloids",

author = "Finke, {A. O.} and Mironov, {M. E.} and Pokrovskii, {M. A.} and Shults, {E. E.}",

note = "The work was supported by a grant from the Russian Science Foundation (Project No. 18-13-00361). We thank staff of the Khimiya Center for Collective Use, SB, RAS, for performing the spectral and analytical studies.",

year = "2023",

month = jan,

doi = "10.1007/s10600-023-03924-w",

language = "English",

volume = "59",

pages = "87--93",

journal = "Chemistry of Natural Compounds",

issn = "0009-3130",

publisher = "Springer New York",

number = "1",

}

RIS

TY - JOUR

T1 - Mannich Reaction of Solasodine with Acetylenes and Formaldehyde. Cytotoxicity of N-Propargyl-Substituted Alkaloid Derivatives

AU - Finke, A. O.

AU - Mironov, M. E.

AU - Pokrovskii, M. A.

AU - Shults, E. E.

N1 - The work was supported by a grant from the Russian Science Foundation (Project No. 18-13-00361). We thank staff of the Khimiya Center for Collective Use, SB, RAS, for performing the spectral and analytical studies.

PY - 2023/1

Y1 - 2023/1

N2 - 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.

AB - 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.

KW - Mannich reaction

KW - acetylene

KW - cytotoxicity

KW - solasodine

KW - steroidal alkaloids

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85149044062&origin=inward&txGid=e8e30c1828842c4f7debe1e236be8149

UR - https://www.mendeley.com/catalogue/a9f3243b-162b-3620-a7fc-21f3dbeeab6a/

U2 - 10.1007/s10600-023-03924-w

DO - 10.1007/s10600-023-03924-w

M3 - Article

VL - 59

SP - 87

EP - 93

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

SN - 0009-3130

IS - 1

ER -

ID: 56394326