PSEUDOPEPTIDES BASED ON NICOTINIC ACID WITH 4-AMIDOXIME UNIT

Authors

  • Volodymyr A. Tkachuk Faculty of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601; Enamine Ltd., 78 Winston Churchill St., Kyiv 02094
  • Pavlo V. Reheda Faculty of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601; Enamine Ltd., 78 Winston Churchill St., Kyiv 02094
  • Andriy V. Kozytskiy Enamine Ltd., 78 Winston Churchill St., Kyiv 02094; ChemBioCenter, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601
  • Svitlana V. Shishkina State Scientific Institution ''Institute for Single Crystals'' of the National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61001
  • Olga V. Hordiyenko Faculty of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601

Keywords:

4-cyanonicotinic acid, Pyrrolidine ring opening, Amidoximes, methyl 2-(1-imino-3-oxo-1,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2-yl)alkanoates, monoimino derivatives of pyrrolo[3,4-c]pyridine-1,3(2H)-dione, pseudopeptides

Abstract

The carbodiimide-mediated coupling of 4-cyanonicotinic acid with L-amino acid methyl esters takes place with the predominant formation of bicyclic compounds – methyl 2-(1-imino-3-oxo-1,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2-yl)alkanoates, which are monoimino derivatives of 4-azaphthalimide. Under the action of hydroxylamine they undergo pyrrolidine cycle opening with the formation of pseudopeptides – coupling products of nicotinic acid with amino acid esters bearing an amidoxime function at position 4.

Author Biographies

Volodymyr A. Tkachuk, Faculty of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601; Enamine Ltd., 78 Winston Churchill St., Kyiv 02094

Faculty of Chemistry

Pavlo V. Reheda, Faculty of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601; Enamine Ltd., 78 Winston Churchill St., Kyiv 02094

Faculty of Chemistry

Olga V. Hordiyenko, Faculty of Chemistry, Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01601

Dr. Olga Hordiyenko

Associate Professor, Faculty of Chemistry

Taras Shevchenko National University of Kyiv

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Published

2024-01-10

Issue

Vol. 59 No. 11/12 (2023)

Section

Original Papers