IMPROVED SYNTHESIS OF TWO QUISQUALIC ACID ANALOGS CONTAINING HYDANTOIN AND IMIDAZOLIDINONE MOIETIES

Authors

  • Aleksandr P. Makhin Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Higher Chemical College of the Russian Academy of Sciences, D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047 https://orcid.org/0009-0001-8619-2415
  • Vasily S. Miturich Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Faculty of Chemistry, National Research University Higher School of Economics, 7 Vavilova St., Moscow 119048 https://orcid.org/0009-0009-1288-5583
  • Matvey V. Vavilov Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Faculty of Biology and Biotechnology, National Research University Higher School of Economics, 33-4 Profsoyuznaya St., Moscow 117418 https://orcid.org/0000-0002-0561-1340
  • Maria S. Lyakhovich Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 https://orcid.org/0000-0001-7774-5527
  • Anastasia A. Andrianova Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Faculty of Medicine, Lomonosov Moscow State University, 27-1 Lomonosov Ave., Moscow 119991 https://orcid.org/0000-0003-1223-4552
  • Renata I. Zagitova Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 https://orcid.org/0000-0001-5065-1360
  • Vladimir I. Shmygarev Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 https://orcid.org/0009-0009-8472-8528
  • Anastasia A. Fadeeva Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 https://orcid.org/0000-0003-0417-5812
  • Oleg N. Yatskin Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 https://orcid.org/0000-0002-2050-8069
  • Olga A. Belozerova Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 https://orcid.org/0000-0002-5603-5371
  • Aristides Tsatsakis Siberian Federal Scientific Centre of Agrobiotechnology, Russian Academy of Sciences, 2B Centralnaya St., Krasnoobsk 630501
  • Ilia V. Yampolsky Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Siberian Federal Scientific Centre of Agrobiotechnology, Russian Academy of Sciences, 2B Centralnaya St., Krasnoobsk 630501. Institute of Translational Medicine, Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997 https://orcid.org/0000-0003-2558-2476
  • Zinaida M. Kaskova Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Siberian Federal Scientific Centre of Agrobiotechnology, Russian Academy of Sciences, 2B Centralnaya St., Krasnoobsk 630501. Institute of Translational Medicine, Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997 https://orcid.org/0000-0001-6336-060X

Keywords:

amino acids, cyclization, nitrogen heterocycles, reductive amination, SARS-CoV-2 main protease inhibitors

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.

Author Biography

Zinaida M. Kaskova, Laboratory of Chemistry of Metabolic Pathways, Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997. Siberian Federal Scientific Centre of Agrobiotechnology, Russian Academy of Sciences, 2B Centralnaya St., Krasnoobsk 630501. Institute of Translational Medicine, Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997

https://www.researchgate.net/profile/Zinaida-Kaskova

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Published

2024-08-01

Issue

Vol. 60 No. 5/6 (2024)

Section

Original Papers