Regioselective acylation of congeners of 3-amino-1H-pyrazolo[3,4-b]quinolines, their activity on bacterial serine/threonine protein kinases and in vitro antibacterial (including antimycobacterial) activity

Abstract

It was found by virtual screening that 3-amino-1H-pyrazolo[3,4-b]quinolines could have wide protein kinase inhibitory activity. Amides of titled amines and thioureas were synthesized regioselectively. 3-Amino-7-methoxy-1H-pyrazolo[3,4-b]quinoline demonstrated in vitro significant inhibitory activity on bacterial serine/threonine protein kinases (inhibition of resistance to kanamycin in Streptomyces lividans regulated by protein kinases). The studies of Structure Activity Relationship (SAR) showed that the substitution of the NH₂ group and 1-NH of pyrazole ring or aromatic ring at the position 6 decreased or removed inhibitory activity.

Keywords::

• Regioselective acylation
• 3-amino-1H-pyrazolo[3,4-b]quinoline
• bacterial
• serine/threonine protein kinase

Acknowledgment

We gratefully acknowledge the excellent technical assistance of Dr. Korolev A.M. for ESI – mass spectrometry and Dr. Luzikov Y.N. for NMR spectra; both are from Gause institute of new antibiotics.

Declaration of interest

Authors report no conflicts of interest.