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Synthesis, structure and biological activity 3- (arylmethyl) aminopyridine-2 (1H) -ones and 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones. / Kulakov, Ivan V.; Palamarchuk, Irina V.; Shulgau, Zarina T. и др.
в: Journal of Molecular Structure, Том 1166, 15.08.2018, стр. 262-269.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Synthesis, structure and biological activity 3- (arylmethyl) aminopyridine-2 (1H) -ones and 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones
AU - Kulakov, Ivan V.
AU - Palamarchuk, Irina V.
AU - Shulgau, Zarina T.
AU - Seilkhanov, Tulegen M.
AU - Gatilov, Yuriy V.
AU - Fisyuk, Alexander S.
N1 - Publisher Copyright: © 2018 Elsevier B.V.
PY - 2018/8/15
Y1 - 2018/8/15
N2 - 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-b][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 1H and 13C NMR 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.
AB - 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-b][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 1H and 13C NMR 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.
KW - 1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ones
KW - 3-Amino-6-methyl-4-phenylpyridin-2(1H)-one
KW - Antiradical activity
KW - Intramolecular cyclization
KW - NMR spectroscopy
KW - Single crystal X-ray diffraction
KW - DESIGN
KW - PEPTIDOMIMETICS
KW - REVERSE-TRANSCRIPTASE INHIBITORS
KW - ANALOGS
KW - 2-PYRIDINONE DERIVATIVES
UR - http://www.scopus.com/inward/record.url?scp=85047396002&partnerID=8YFLogxK
U2 - 10.1016/j.molstruc.2018.04.036
DO - 10.1016/j.molstruc.2018.04.036
M3 - Article
AN - SCOPUS:85047396002
VL - 1166
SP - 262
EP - 269
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
SN - 0022-2860
ER -
ID: 13594916