3-HETARYLISOCOUMARINS IN THE SYNTHESIS OF 1-FUNCTIONALIZED 3-HETARYLISOQUINOLINES

Authors

  • Artem S. Konovalenko V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kyiv 02094, Ukraine
  • Oleh V. Shablykin V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kyiv 02094, Ukraine
  • Volodymyr S. Brovarets V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kyiv 02094, Ukraine
  • Olga V. Shablykina Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01033, Ukraine V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanska St., Kyiv 02094, Ukraine
  • Viktoriia S. Moskvina Taras Shevchenko National University of Kyiv, 60 Volodymyrska St., Kyiv 01033, Ukraine V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry NAS of Ukraine, 1 Murmanska St., Kyiv 02094, Ukraine
  • Andriy V. Kozytskiy L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028, Ukraine

DOI:

https://doi.org/10.1007/5648

Keywords:

isocoumarin, isoquinoline, isoquinolin-1(2H)-ones, nitrogen-containing heterocycles, anticancer activity, recyclization.

Abstract

A convenient method was developed for the synthesis of novel isoquinolin-1(2H)-ones, 1-chloroisoquinolines, and 1-aminoisoquinolines with a heterocyclic substituent in position 3 via a recyclization of 3-hetarylisocoumarins with (NH4)2CO3. 1-Aminoisoquinolines were efficiently obtained from corresponding 1-chloro-3-hetarylisoquinolines (obtained by interaction of isoquinolin-1(2H)-ones with POCl3) and cyclic secondary amines (morpholine or 1-methylpiperazine). Literature data and preliminary results of biological assays allow to consider 1-amino-3-hetarylisoquinolines a promising family of anticancer compounds.

Author Biography

Andriy V. Kozytskiy, L. V. Pisarzhevskii Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 Nauky Ave., Kyiv 03028, Ukraine

L.V. Pisarzhevskii Institute of Physical Chemistry of NAS of Ukraine,

31 Nauky Avenue, Kyiv 03028, Ukraine

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Published

2020-09-17

Issue

Vol. 56 No. 8 (2020)

Section

Original Papers