Polysubstituted pyrans, chromenes, and chromenopyridines with isoxazole or isothiazole moiety: synthesis, structure, and antitumor activity

Authors

  • Vladimir I. Potkin Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
  • Irina A. Kolesnik Institute of physical organic chemistry of National academy of sciences of Belarus
  • Ekaterina Akishina Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus
  • Fedor I. Zubkov RUDN University
  • Milana A. Fedoseeva RUDN University
  • Anastasia A. Pronina RUDN University
  • Mikhail C. Grigoriev Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
  • Hongwei Zhou Jiaxing University
  • Peter V. Kurman Institute of Biorganic Chemistry, National Academy of Sciences of Belarus
  • Tatiana I. Terpinskaya Institute of Physiology, National Academy of Sciences of Belarus
  • Mariya A. Rubinskaya Institute of Physiology, National Academy of Sciences of Belarus

Keywords:

aldehydes, chromenes, chromenopyridines, isothiazoles, pyrans, Knoevenagel reaction

Abstract

Polysubstituted derivatives of pyrans, chromenes, and chromeno[2,3-b]pyridines incorporating a 4,5-dichloroisothiazole or 5-arylisoxazole-3-carbaldehyde fragment in the molecule were synthesized by successive and one-step three-component reactions of 4,5dichloroisothiazole-3-carbaldehyde and 5-arylisoxazole-3-carbaldehyde with various 1,3-diketones, malononitrile or its dimer. The structure of the target products was proven by X-ray structural analysis. Notably, it was found that the planes of the azole and chromene rings in the molecules of (1,2-azol-3-yl)chromenes are almost perpendicular. Intrinsic antitumor activity and synergistic enhancement of the activity in combination with known cytostatics used in the therapy of oncological diseases were found for some of the synthesized compounds.

 

Author Biographies

Vladimir I. Potkin, Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
13 Surganova St., Minsk 220072, Belarus

Irina A. Kolesnik, Institute of physical organic chemistry of National academy of sciences of Belarus

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
13 Surganova St., Minsk 220072, Belarus

Junior reseacher in the Laboratory of organoelement compounds

Ekaterina Akishina, Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus

Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
13 Surganova St., Minsk 220072, Belarus

Fedor I. Zubkov, RUDN University

RUDN University,
6 Miklukho-Maklaya St., Moscow 117198, Russia

Milana A. Fedoseeva, RUDN University

RUDN University,
6 Miklukho-Maklaya St., Moscow 117198, Russia

Anastasia A. Pronina, RUDN University

RUDN University,
6 Miklukho-Maklaya St., Moscow 117198, Russia

Mikhail C. Grigoriev, Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences

Frumkin Institute of Chemistry and Electrochemistry, Russian Academy of Sciences,
31 Leninsky Ave., Moscow 119071, Russia

Hongwei Zhou, Jiaxing University

College of Biological, Chemical Sciences and Engineering, Jiaxing University,
Jiaxing, Zhejiang 314001, China

Peter V. Kurman, Institute of Biorganic Chemistry, National Academy of Sciences of Belarus

Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus,
5/2 Akademika V. F. Kuprevicha St., Minsk 220141, Belarus

Tatiana I. Terpinskaya, Institute of Physiology, National Academy of Sciences of Belarus

Institute of Physiology, National Academy of Sciences of Belarus,
28 Akademicheskaya St., Minsk 220072, Belarus

Mariya A. Rubinskaya, Institute of Physiology, National Academy of Sciences of Belarus

Institute of Physiology, National Academy of Sciences of Belarus,
28 Akademicheskaya St., Minsk 220072, Belarus

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Published

2024-09-25

Issue

Vol. 60 No. 7/8 (2024)

Section

Original Papers