Open Access
Open access
volume 25 issue 1 pages 18

[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones

Juliana V. Kuznetsova 1
Varvara T. Tkachenko 1
Lada M. Petrovskaya 1
Dmitry E. Shybanov 1
Viktor A. Tafeenko 1
Anna S. Pestretsova 2, 3
Vera A. Yakovleva 4
Vadim S. Pokrovsky 2, 4, 5
Publication typeJournal Article
Publication date2023-12-19
scimago Q1
wos Q1
SJR1.273
CiteScore9.0
Impact factor4.9
ISSN16616596, 14220067
PubMed ID:  38203188
Catalysis
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Computer Science Applications
Spectroscopy
Molecular Biology
General Medicine
Abstract

Approximately 1,3-Dipolar cycloaddition of imidazolidine derivatives containing exocyclic double bonds is a convenient method of creating spiro-conjugated molecules with promising anticancer activity. In this work, the derivatives of parabanic acid (2-thioxoimidazolidine-4,5-diones and 5-aryliminoimidazolidine-2,4-diones) were first investigated as dipolarophiles in the reactions with nitrile imines. The generation of nitrile imines was carried out either by the addition of tertiary amine to hydrazonoyl chlorides «drop by drop» or using the recently proposed diffusion mixing technique, which led to ~5–15% increases in target compound yields. It was found that the addition of nitrile imines to C=S or C=N exocyclic double bonds led to 1,2,4-thiazolines or triazolines and occurred regioselectively in accordance with the ratio of FMO coefficients of reactants. The yield of the resulting spiro-compound depended on the presence of alkyl substituents in the nitrile imine structure and was significantly decreased in reactions with imines with strong electron donor or electron-withdrawing groups. Some of the obtained compounds showed reasonable in vitro cytotoxicity. IC50 values were calculated for HCT116 (colon cancer) cells using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) test.

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GOST Copy
Kuznetsova J. V. et al. [3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones // International Journal of Molecular Sciences. 2023. Vol. 25. No. 1. p. 18.
GOST all authors (up to 50) Copy
Kuznetsova J. V., Tkachenko V. T., Petrovskaya L. M., Filkina M. E., Shybanov D. E., Grishin Y. K., Roznyatovsky V. A., Tafeenko V. A., Pestretsova A. S., Yakovleva V. A., Pokrovsky V. S., Kukushkin M. E., Beloglazkina E. K. [3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones // International Journal of Molecular Sciences. 2023. Vol. 25. No. 1. p. 18.
RIS |
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RIS Copy
TY - JOUR
DO - 10.3390/ijms25010018
UR - https://www.mdpi.com/1422-0067/25/1/18
TI - [3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones
T2 - International Journal of Molecular Sciences
AU - Kuznetsova, Juliana V.
AU - Tkachenko, Varvara T.
AU - Petrovskaya, Lada M.
AU - Filkina, Maria E
AU - Shybanov, Dmitry E.
AU - Grishin, Yuri K.
AU - Roznyatovsky, Vitaly A
AU - Tafeenko, Viktor A.
AU - Pestretsova, Anna S.
AU - Yakovleva, Vera A.
AU - Pokrovsky, Vadim S.
AU - Kukushkin, Maxim E.
AU - Beloglazkina, Elena K.
PY - 2023
DA - 2023/12/19
PB - MDPI
SP - 18
IS - 1
VL - 25
PMID - 38203188
SN - 1661-6596
SN - 1422-0067
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Kuznetsova,
author = {Juliana V. Kuznetsova and Varvara T. Tkachenko and Lada M. Petrovskaya and Maria E Filkina and Dmitry E. Shybanov and Yuri K. Grishin and Vitaly A Roznyatovsky and Viktor A. Tafeenko and Anna S. Pestretsova and Vera A. Yakovleva and Vadim S. Pokrovsky and Maxim E. Kukushkin and Elena K. Beloglazkina},
title = {[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones},
journal = {International Journal of Molecular Sciences},
year = {2023},
volume = {25},
publisher = {MDPI},
month = {dec},
url = {https://www.mdpi.com/1422-0067/25/1/18},
number = {1},
pages = {18},
doi = {10.3390/ijms25010018}
}
MLA
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MLA Copy
Kuznetsova, Juliana V., et al. “[3+2]-Cycloaddition of Nitrile Imines to Parabanic Acid Derivatives—An Approach to Novel Spiroimidazolidinediones.” International Journal of Molecular Sciences, vol. 25, no. 1, Dec. 2023, p. 18. https://www.mdpi.com/1422-0067/25/1/18.