SYNTHESIS, X-RAY AND DFT STUDIES OF 6-HALO-3-(HYDROXYMETHYL)CINNOLIN-4(1<i>H</i>)-ONES

Authors

  • Anastasia A. Babushkina Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Vladimir N. Mikhaylov Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Alexander S. Novikov Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Viktor N. Sorokoumov Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Maxim A. Gureev Research Center ''Digital Biodesign and Personalized Healthcare'', I. M. Sechenov First Moscow State Medical University, 8-2 Trubetskaya St., Moscow 119991
  • Mariya A. Kryukova Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Alexander O. Shpakov Sechenov Institute of Evolutionary Biology and Biochemistry, Russian Academy of Sciences, 44 Toreza Ave., Saint Petersburg 194223
  • Irina A. Balova Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

DOI:

https://doi.org/10.1007/6784

Keywords:

cinnolines, bifurcated bonds, cross coupling, DFT calculations, tyrosine phosphatase 1В inhibitors, Richter cyclization

Abstract

The Richter cyclization was used for the synthesis of 6-halo-3-(hydroxymethyl)cinnolin-4(1H)-ones. X-ray analysis revealed that these compounds exist as dimers in their crystal state, wherein two molecules are linked by intermolecular double and bifurcated hydrogen bonds that can explain their low solubility. Theoretical study of bifurcated hydrogen bonds responsible for the dimerization was carried out by DFT calculations as well as by topological analysis of the electron density distribution within the framework of Bader's theory.

Author Biography

Vladimir N. Mikhaylov, Institute of Chemistry, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

Кафедра органической химии, доцент

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Published

2022-09-20

Issue

Vol. 58 No. 8/9 (2022)

Section

Original Papers