Chemistry of Heterocyclic Compounds

, volume 60 , issue 5-6 , pages 262-268

Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties

Aleksandr P. Makhin ^{1, 2}

Vasily S. Miturich ^{1, 3}

Matvey V Vavilov ^{1, 4}

Maria S Lyakhovich ^{1, 5}

Anastasia A Andrianova ^{1, 6}

Renata I Zagitova ¹

Vladimir I. Shmygarev ¹

Anastasia A Fadeeva ¹

Oleg N Yatskin ¹

Olga A Belozerova ¹

Aristides Tsatsakis ⁷

Ilia V Yampolsky ^{1, 7, 8}

Zinaida M Kaskova ^{1, 7, 8}

Hide authors affiliations Show authors affiliations: 8 affiliations

Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia |

Higher Chemical College of the Russian Academy of Sciences, D. Mendeleev University of Chemical Technology of Russia, Moscow, Russia |

Faculty of Chemistry, National Research University Higher School of Economics, Moscow, Russia |

⁴

Faculty of biology and biotechnology, National Research University Higher School of Economics, Moscow, Russia |

⁵

FineTech Pharmaceutical Ltd, Nesher, Israel |

⁶

Faculty of Medicine, Lomonosov Moscow State University, Moscow, Russia |

⁷

Siberian Federal Scientific Centre of Agrobiotechnology, Russian Academy of Sciences, Krasnoobsk, Russia |

⁸

Institute of Translational Medicine, Pirogov Russian National Research Medical University, Moscow, Russia |

Publication type: Journal Article

Publication date: 2024-06-01

Springer Nature

Chemistry of Heterocyclic Compounds

scimago Q4

wos Q4

SJR: 0.243

CiteScore: 2.7

Impact factor: 1.0

ISSN: 00093122, 15738353

DOI: 10.1007/s10593-024-03331-1

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Abstract

In the light of recent progress in the development of SARS-CoV-2 main protease inhibitors, the synthesis of their key fragment, heterocyclic amino acids, is of great interest. Here, we report a method for the preparation of two new quisqualic acid analogs containing hydantoin and imidazolidinone moieties. The hydantoin analog was obtained using an amide ester cyclization, while the imidazolidinone unit was constructed by reductive amination and subsequent cyclization of a substituted ethylenediamine with carbonyldiimidazole. The presented approach provides the convergent synthesis of target analogs in 8 and 5 steps respectively.

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Makhin A. P. et al. Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties // Chemistry of Heterocyclic Compounds. 2024. Vol. 60. No. 5-6. pp. 262-268.

GOST all authors (up to 50) Copy

Makhin A. P., Miturich V. S., Vavilov M. V., Lyakhovich M. S., Andrianova A. A., Zagitova R. I., Shmygarev V. I., Fadeeva A. A., Yatskin O. N., Belozerova O. A., Tsatsakis A., Yampolsky I. V., Kaskova Z. M. Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties // Chemistry of Heterocyclic Compounds. 2024. Vol. 60. No. 5-6. pp. 262-268.

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TY - JOUR

DO - 10.1007/s10593-024-03331-1

UR - https://link.springer.com/10.1007/s10593-024-03331-1

TI - Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties

T2 - Chemistry of Heterocyclic Compounds

AU - Makhin, Aleksandr P.

AU - Miturich, Vasily S.

AU - Vavilov, Matvey V

AU - Lyakhovich, Maria S

AU - Andrianova, Anastasia A

AU - Zagitova, Renata I

AU - Shmygarev, Vladimir I.

AU - Fadeeva, Anastasia A

AU - Yatskin, Oleg N

AU - Belozerova, Olga A

AU - Tsatsakis, Aristides

AU - Yampolsky, Ilia V

AU - Kaskova, Zinaida M

PY - 2024

DA - 2024/06/01

PB - Springer Nature

SP - 262-268

IS - 5-6

VL - 60

SN - 0009-3122

SN - 1573-8353

ER -

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@article{2024_Makhin,

author = {Aleksandr P. Makhin and Vasily S. Miturich and Matvey V Vavilov and Maria S Lyakhovich and Anastasia A Andrianova and Renata I Zagitova and Vladimir I. Shmygarev and Anastasia A Fadeeva and Oleg N Yatskin and Olga A Belozerova and Aristides Tsatsakis and Ilia V Yampolsky and Zinaida M Kaskova},

title = {Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties},

journal = {Chemistry of Heterocyclic Compounds},

year = {2024},

volume = {60},

publisher = {Springer Nature},

month = {jun},

url = {https://link.springer.com/10.1007/s10593-024-03331-1},

number = {5-6},

pages = {262--268},

doi = {10.1007/s10593-024-03331-1}

}

MLA

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Makhin, Aleksandr P., et al. “Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties.” Chemistry of Heterocyclic Compounds, vol. 60, no. 5-6, Jun. 2024, pp. 262-268. https://link.springer.com/10.1007/s10593-024-03331-1.