Synthesis, crystal structure and biological activity of diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3-thiadi azol-5-yl)pyridine-3,5- dicarboxylate / Li J.-J., Ji X.-T., Huang Y., Morzherin Y.Yu., Hua X.-W., Zong G.-N., Song H.-B., Belskaya N.P., Fan Z.-J., Li F.-Y., Liu C.-L., Bakulev V.A. // Jiegou Huaxue. - 2014. - V. 33, l. 4. - P. 535-543.

ISSN:
02545861
Type:
Article
Abstract:
The title compound diethyl 1,4-dihydro-2,6-dimethyl-4-(4-methyl-1,2,3- thiadiazol-5-yl) pyridine-3,5-dicarboxylate (C16H21N 3O4S, Mr = 351.42) was prepared by the Hantszch reaction with 4-methyl-1,2,3-thiadiazole-5-formaldehyde, ethyl acetoacetate and ammonium acetate in the presence of aluminum chloride in alcohol, and its structure was characterized by IR spectra, 1H-NMR, EA, and single-crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group P21/n with a = 11.300(2), b = 12.771(3), c = 12.826(3) Å, β = 96.55(3)°, V = 1839.0(6) Å3, Z = 4, Dc = 1.296 g/cm3, μ(MoKa) = 0.71073 mm-1, F(000) = 744, R = 0.0981 and wR = 0.1994. X-ray diffraction result shows that the torsion angles of N(1)-C(2)-C(3)-C(4) and C(2)-C(3)-C(4)-C(8) are 178.9(3)° and -130.3(3)°, respectively. All rings in the title compound are non-planar. The bioassay results indicate that the title compound has good fungicidal activity, good antivirus activity against tobacco mosaic virus and certain extent of insecticidal activity against Mythimna separata.
Author keywords:
1,2,3-thiadiazole; 1,4-dihydropyridine; Biological activity; Crystal structure
Index keywords:
нет данных
DOI:
нет данных
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Affiliations Department of Plant Pathology, Sichuan Agricultural University, Chengdu 611130, China; State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, China; Ural Federal University Named after the First President of Russia B. N. Yeltsin, Yeltsin UrFU 620002, Ekaterinburg, Russian Federation
Author Keywords 1,2,3-thiadiazole; 1,4-dihydropyridine; Biological activity; Crystal structure
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Correspondence Address Huang, Y.; Department of Plant Pathology, Sichuan Agricultural University, Chengdu 611130, China; email: 5787huangyun@sina.com
Publisher Fujian Institute of Research of the Structure of Matter
Language of Original Document English
Abbreviated Source Title Jiegou Huaxue
Source Scopus