Synthesis, structure and biological activity 3-(arylmethyl) aminopyridine-2 (1H) -ones and 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones

Synthesis, structure and biological activity 3-(arylmethyl) aminopyridine-2 (1H) -ones and 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones Full article

Journal

Journal of Molecular Structure
ISSN: 0022-2860 , E-ISSN: 1872-8014

Output data

Year: 2018, Volume: 1166, Pages: 262-269 Pages count : DOI: 10.1016/j.molstruc.2018.04.036

Tags

3-Amino-6-methyl-4-phenylpyridin-2(1H)-one; 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones; Intramolecular cyclization; Antiradical activity; NMR spectroscopy; Single crystal X-ray diffraction

Authors

Kulakov Ivan, V ¹ , Palamarchuk Irina, V ¹ , Shulgau Zarina T. ² , Seilkhanov Tulegen M. ³ , Gatilov Yuriy, V ^4,5 , Fisyuk Alexander S. ^1,6

Affiliations

1	(Данные Web of science) Omsk FM Dostoevsky State Univ, Dept Organ Chem, 55a Mira Ave, Omsk 644077, Russia
2	(Данные Web of science) Minist Educ & Sci, RSE Natl Ctr Biotechnol, 13-5 Kurgalzhynskoe Rd, Astana 010000, Kazakhstan
3	(Данные Web of science) Sh Ualikhanov Kokshetau State Univ, 76 Abaya St, Kokshetau 020000, Kazakhstan
4	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Akad Lavrientieva Ave, Novosibirsk 630090, Russia
5	(Данные Web of science) Novosibirsk State Univ, 2 Pirogov St, Novosibirsk 630090, Russia
6	(Данные Web of science) Omsk State Tech Univ, Lab New Organ Mat, 11 Mira Ave, Omsk 644050, Russia

Reaction of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one with aromatic aldehydes afforded the corresponding Schiff bases, the reduction of which with sodium borohydride led to the formation of 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-ones. Acylation of 3-amino-6-methyl-4-phenylpyridin-2(1H)-one with chloroacetyl chloride resulted either in the corresponding chloroacetamides or in 1H-pyrido[2,3-13][1,4]oxazin-2(3H)-ones. A possibility to form octahedral complex with calcium chloride was demonstrated by the example of 3-(benzylamino)-6-methyl-4-phenylpyridin-2(1H)-one. Structure of all the prepared compounds was proved by H-1 and (CNMR)-C-13 spectroscopy, as well as single crystal X-ray diffraction method. Among a series of novel compounds, 3-(arylmethyl)-6-methyl-4-phenylpyridin-2(1H)-one derivatives showed antiradical activity against DPPH and ABTS radicals. (C) 2018 Elsevier B.V. All rights reserved.

Kulakov I.V. , Palamarchuk I.V. , Shulgau Z.T. , Seilkhanov T.M. , Gatilov Y.V. , Fisyuk A.S.
Synthesis, structure and biological activity 3-(arylmethyl) aminopyridine-2 (1H) -ones and 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones
Journal of Molecular Structure. 2018. V.1166. P.262-269. DOI: 10.1016/j.molstruc.2018.04.036 WOS Scopus РИНЦ

Published print:

Aug 1, 2018

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