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Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes. / Gromova, M. A.; Kharitonov, Y. u.V.; Pokrovskii, M. A. et al.

In: Chemistry of Natural Compounds, Vol. 55, No. 1, 15.01.2019, p. 52-59.

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

Harvard

Gromova, MA, Kharitonov, YUV, Pokrovskii, MA, Bagryanskaya, IY, Pokrovskii, AG & Shul’ts, EE 2019, 'Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes', Chemistry of Natural Compounds, vol. 55, no. 1, pp. 52-59. https://doi.org/10.1007/s10600-019-02613-x

APA

Gromova, M. A., Kharitonov, Y. U. V., Pokrovskii, M. A., Bagryanskaya, I. Y., Pokrovskii, A. G., & Shul’ts, E. E. (2019). Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes. Chemistry of Natural Compounds, 55(1), 52-59. https://doi.org/10.1007/s10600-019-02613-x

Vancouver

Gromova MA, Kharitonov YUV, Pokrovskii MA, Bagryanskaya IY, Pokrovskii AG, Shul’ts EE. Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes. Chemistry of Natural Compounds. 2019 Jan 15;55(1):52-59. doi: 10.1007/s10600-019-02613-x

Author

Gromova, M. A. ; Kharitonov, Y. u.V. ; Pokrovskii, M. A. et al. / Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes. In: Chemistry of Natural Compounds. 2019 ; Vol. 55, No. 1. pp. 52-59.

BibTeX

@article{1ddba1a6fcae4fffb7abaa437be7b0c2,
title = "Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes",
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.",
keywords = "1,2,3-triazoles, amino acids, cytotoxicity, diterpenoids, isopimaric acid, XSA",
author = "Gromova, {M. A.} and Kharitonov, {Y. u.V.} and Pokrovskii, {M. A.} and Bagryanskaya, {I. Yu} and Pokrovskii, {A. G.} and Shul{\textquoteright}ts, {E. E.}",
year = "2019",
month = jan,
day = "15",
doi = "10.1007/s10600-019-02613-x",
language = "English",
volume = "55",
pages = "52--59",
journal = "Chemistry of Natural Compounds",
issn = "0009-3130",
publisher = "Springer New York",
number = "1",

}

RIS

TY - JOUR

T1 - Synthetic Transformations of Higher Terpenoids. 37. Synthesis and Cytotoxicity of 4-(Oxazol-2-Yl)-18-Norisopimaranes

AU - Gromova, M. A.

AU - Kharitonov, Y. u.V.

AU - Pokrovskii, M. A.

AU - Bagryanskaya, I. Yu

AU - Pokrovskii, A. G.

AU - Shul’ts, E. E.

PY - 2019/1/15

Y1 - 2019/1/15

N2 - 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.

AB - 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.

KW - 1,2,3-triazoles

KW - amino acids

KW - cytotoxicity

KW - diterpenoids

KW - isopimaric acid

KW - XSA

UR - http://www.scopus.com/inward/record.url?scp=85063134864&partnerID=8YFLogxK

U2 - 10.1007/s10600-019-02613-x

DO - 10.1007/s10600-019-02613-x

M3 - Article

AN - SCOPUS:85063134864

VL - 55

SP - 52

EP - 59

JO - Chemistry of Natural Compounds

JF - Chemistry of Natural Compounds

SN - 0009-3130

IS - 1

ER -

ID: 18949672