ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and neurotropic activity of new 3-(arylmethyl)aminopyridine-2(1H)-one

Irina V. Palamarchuk, Zarina T. Shulgau, Margarita A. Kharitonova, and Ivan V. Kulakov

Institute of Chemistry, Tyumen State University, Tyumen, Russia

E-mail: shulgau@biocenter.kz

Received: 23 November 2020  Accepted: 10 May 2021

Abstract:

The reaction of 3-amino-6-methyl-4-phenylpyridine-2(1H)-one with aromatic aldehydes resulted in the corresponding Schiff bases, which reduction with sodium borohydride led to the formation of 3-(arylmethylamino)-6-methyl-4-phenylpyridine-2(1H)-ones. The structure of all prepared compounds was proved by ¹H and ¹³C NMR spectroscopy. The initial evaluation of the synthesized compounds in vivo was carried out for a tranquilizing (anxiolytic) activity by «light–dark box test» and antidepressant activity by Porsolt’s «behavioral despair test». Several derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridine-2(1H)-one with higher potential neurotropic activity than that of the comparator drugs (Mexidol and Amitriptyline) were detected.

Graphic abstract

Keywords: 3-amino-6-methyl-4-phenylpyridin-2(1H)-one; 3-(arylmethyl)-6-methyl-4-phenylpyridine-2(1H)-one; Anxiolytic and antidepressant activities

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01696-7

Chemical Papers 75 (9) 4729–4739 (2021)