SYNTHESIS AND EVALUATION OF THE CYTOTOXICITY OF FURANOLABDANOIDS CONTAINING A 3-AMINOPROPANOYL SUBSTITUENT IN THE FURAN RING

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SYNTHESIS AND EVALUATION OF THE CYTOTOXICITY OF FURANOLABDANOIDS CONTAINING A 3-AMINOPROPANOYL SUBSTITUENT IN THE FURAN RING. / YU.V., KHARITONOV; D.A., PETROVA; E.E., SHULTS и др.

в: Chemistry for Sustainable Development, Том 31, № 6, 2023, стр. 715-723.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Author

YU.V., KHARITONOV ; D.A., PETROVA ; E.E., SHULTS и др. / SYNTHESIS AND EVALUATION OF THE CYTOTOXICITY OF FURANOLABDANOIDS CONTAINING A 3-AMINOPROPANOYL SUBSTITUENT IN THE FURAN RING. в: Chemistry for Sustainable Development. 2023 ; Том 31, № 6. стр. 715-723.

BibTeX

@article{07e1fc9e7d0e4f27bb37d1741f41e55e,

title = "SYNTHESIS AND EVALUATION OF THE CYTOTOXICITY OF FURANOLABDANOIDS CONTAINING A 3-AMINOPROPANOYL SUBSTITUENT IN THE FURAN RING",

abstract = "15-Acetyl- and 16-acetylfuranolabdanoids were synthesised by the acetylation of the methyl ester of lambertianic acid with acetic anhydride in the presence of Mg(ClO4)2 and used as starting compounds for the preparation of 15- or 16-(3-aminopropanoyl)methyllambertianates. The proposed approach involved silylation of 15-acetyl- or 16-acetylmethyllambertianate and the Mannich reaction of the resulting enol silyl ester with N,N-disubstituted methyleneiminium salts. The synthesized compounds possessed cytotoxicity on tumour cell lines CCRF CEM, MCF7 and PC-3 (MTT test). The compounds containing a 3-morpholinopropanoyl or 3-pyrrolidinopropanoyl substituent at the C-16 position of methyl lambertianate selectively inhibited the growth of human T-cell leukemia cells (GI50 was 5.8-6.1 μM) and exhibited cytotoxicity an order of magnitude higher than the parent compound lambertianic acid.",

keywords = "DITERPENOIDS, LAMBERTIANIC ACID, MANNICH REACTION, CYTOTOXICITY",

author = "KHARITONOV YU.V. and PETROVA D.A. and SHULTS E.E. and POKROVSKII M.A. and POKROVSKII A.G.",

note = "Synthesis and Evaluation of the Cytotoxicity of Furanolabdanoids Containing a 3-Aminopropanoyl Substituent in the Furan Ring / Yu. V. Kharitonov, D. A. Petrova, E. E. Shults [et al.] // Chemistry for Sustainable Development. – 2023. – Vol. 31, No. 6. – P. 715-723. – DOI 10.15372/CSD2023521.",

year = "2023",

doi = "10.15372/csd2023521",

language = "English",

volume = "31",

pages = "715--723",

journal = "Chemistry for Sustainable Development",

issn = "1817-1818",

publisher = "ФГУП {"}Издательство СО РАН{"}",

number = "6",

}

RIS

TY - JOUR

T1 - SYNTHESIS AND EVALUATION OF THE CYTOTOXICITY OF FURANOLABDANOIDS CONTAINING A 3-AMINOPROPANOYL SUBSTITUENT IN THE FURAN RING

AU - YU.V., KHARITONOV

AU - D.A., PETROVA

AU - E.E., SHULTS

AU - M.A., POKROVSKII

AU - A.G., POKROVSKII

N1 - Synthesis and Evaluation of the Cytotoxicity of Furanolabdanoids Containing a 3-Aminopropanoyl Substituent in the Furan Ring / Yu. V. Kharitonov, D. A. Petrova, E. E. Shults [et al.] // Chemistry for Sustainable Development. – 2023. – Vol. 31, No. 6. – P. 715-723. – DOI 10.15372/CSD2023521.

PY - 2023

Y1 - 2023

N2 - 15-Acetyl- and 16-acetylfuranolabdanoids were synthesised by the acetylation of the methyl ester of lambertianic acid with acetic anhydride in the presence of Mg(ClO4)2 and used as starting compounds for the preparation of 15- or 16-(3-aminopropanoyl)methyllambertianates. The proposed approach involved silylation of 15-acetyl- or 16-acetylmethyllambertianate and the Mannich reaction of the resulting enol silyl ester with N,N-disubstituted methyleneiminium salts. The synthesized compounds possessed cytotoxicity on tumour cell lines CCRF CEM, MCF7 and PC-3 (MTT test). The compounds containing a 3-morpholinopropanoyl or 3-pyrrolidinopropanoyl substituent at the C-16 position of methyl lambertianate selectively inhibited the growth of human T-cell leukemia cells (GI50 was 5.8-6.1 μM) and exhibited cytotoxicity an order of magnitude higher than the parent compound lambertianic acid.

AB - 15-Acetyl- and 16-acetylfuranolabdanoids were synthesised by the acetylation of the methyl ester of lambertianic acid with acetic anhydride in the presence of Mg(ClO4)2 and used as starting compounds for the preparation of 15- or 16-(3-aminopropanoyl)methyllambertianates. The proposed approach involved silylation of 15-acetyl- or 16-acetylmethyllambertianate and the Mannich reaction of the resulting enol silyl ester with N,N-disubstituted methyleneiminium salts. The synthesized compounds possessed cytotoxicity on tumour cell lines CCRF CEM, MCF7 and PC-3 (MTT test). The compounds containing a 3-morpholinopropanoyl or 3-pyrrolidinopropanoyl substituent at the C-16 position of methyl lambertianate selectively inhibited the growth of human T-cell leukemia cells (GI50 was 5.8-6.1 μM) and exhibited cytotoxicity an order of magnitude higher than the parent compound lambertianic acid.

KW - DITERPENOIDS

KW - LAMBERTIANIC ACID

KW - MANNICH REACTION

KW - CYTOTOXICITY

UR - https://www.mendeley.com/catalogue/68765ede-26ea-3d7c-9dac-034cc02dfe13/

UR - https://www.elibrary.ru/item.asp?id=59461438

U2 - 10.15372/csd2023521

DO - 10.15372/csd2023521

M3 - Article

VL - 31

SP - 715

EP - 723

JO - Chemistry for Sustainable Development

JF - Chemistry for Sustainable Development

SN - 1817-1818

IS - 6

ER -

ID: 68317214