Synthesis, crystal structure and biological activity of N-(tert-butyl)-N'-(2-(4-chlorophenyl)acetyl)-5-methyl-1,2,3-thiadiazole-4- carbohydrazide / Wang D., Mao W.-T., Fan Z.-J., Li J.-J., Huang Y., Song H.-B., Fan Q., Kalinina T.A., Tatiana G., Yur'evich M.Y., Pavlovna B.N., Alekseevich B.V. // Jiegou Huaxue. - 2013. - V. 32, l. 5. - P. 673-678.

ISSN:
02545861
Type:
Article
Abstract:
The title compound N-(tert-butyl)-N'-(2-(4-chlorophenyl)acetyl)-5-methyl-1, 2,3-thiadiazole-4-carbohydrazide (C16H19ClN 4NaO2S, Mr = 366.86) has been synthesized, and its structure was characterized by IR, 1H NMR, H RMS and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group P1 with a = 8.464(2), b = 10.192(2), c = 11.757(2) Å, α = 68.48(3), β = 76.31(3), γ = 80.86(3)°, Z = 2, V = 2024.6(10) Å3, Dc = 1.333 g/cm3, μ = 0.339 mm-1, F(000) = 384, R = 0.0450 and wR (I > 2σ(I)) = 0.1234. X-ray analysis indicates one N-H···N intermolecular hydrogen bond and no π-π stacking interactions are observed in this crystal structure. The preliminary biological test shows that the title compound has fungicidal activity and antivirus activities against tobacco mosaic virus.
Author keywords:
1,2,3-Thiadiazole; Biological activity; Crystal structure; Synthesis; X-ray diffraction
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; Sichuan Functional Heterocyclic Compounds Engineering Technology Research Center, Lier Chemicals Co., Ltd., No. 97 Mianxingdonglu, Mianyang, Sichuan 621000, China; Ural Federal University, Russia B. N. Yeltsin, Yeltsin UrFU 620002, Ekaterinburg, Russian Federation
Author Keywords 1,2,3-Thiadiazole; Biological activity; Crystal structure; Synthesis; X-ray diffraction
References Wing, K.D., RH 5849, a nonsteroidal ecdysone agonist: Effects on a Drosophila cell line (1988) Science, 241, pp. 467-469; Sun, R.F., Zhang, Y.L., Chen, L., Li, Y.Q., Li, Q.S., Song, H.B., Huang, R.Q., Wang, Q.M., Design, synthesis, and insecticidal activities of new N-benzoyl-N'-phenyl-N'-sulfenylureas (2009) J. Agric. Food Chem., 57, pp. 3661-3668; Sundaram, M., Palli, S.R., Ishaaya, I., Krell, P.J., Retnakaran, A., Toxicity of ecdysone agonists correlates with the induction of CHR3 mRNA in the spruce budworm (1998) Pesticide Biochemistry and Physiology, 62 (3), pp. 201-208. , DOI 10.1006/pest.1998.2383; Zhao, P.-L., Li, J., Yang, G.-F., Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines (2007) Bioorganic and Medicinal Chemistry, 15 (5), pp. 1888-1895. , DOI 10.1016/j.bmc.2007.01.008, PII S0968089607000235; Ruiu, L., Satta, A., Floris, I., Effects of an azadirachtin-based formulation on the non-target muscoid fly parasitoid Muscidifurax raptor (Hymenoptera: Pteromalidae) (2008) Biological Control, 47, pp. 66-70; Shang, J., Sun, R.F., Li, Y.Q., Huang, R.Q., Bi, F.C., Wang, Q.M., Synthesis and insecticidal evaluation of N-tert-butyl-N'-thio[1-(6- chloro-3-pyridylmethyl)-2-nitroiminoimidazolidine]-N, N'-diacylhydrazines (2010) J. Agric. Food Chem., 58, pp. 1834-1837; Li, X.C., Yang, X.L., Cui, Z.N., Li, Y., He, H.W., Ling, Y., Synthesis and bioactivity of novel N, N'-diacylhydrazine derivatives containing furan (II) (2010) Chin. J. Chem., 28, pp. 1233-1239; Mao, C.H., Wang, K.L., Wang, Z.W., Ou, X.M., Huang, R.Q., Bi, F.C., Wang, Q.M., Synthesis and insecticidal evaluation of novel N'-tert-butyl-N'- substitutedbenzoyl-N-5-chloro-6-chromanecarbohydrazide derivatives (2008) Bioorgan. Med. Chem., 16, pp. 488-494; Zhao, Y., Mao, C.H., Li, Y.Q., Zhang, P.X., Huang, Z.Q., Bi, F.C., Huang, R.Q., Wang, Q.M., Synthesis, crystal structure, and insecticidal activity of novel N-alkyloxyoxalyl derivatives of 2-arylpyrrole (2008) J. Agric. Food Chem., 56, pp. 7326-7332; Du, Q.S., Zhu, W.P., Zhao, Z.J., Qian, X.H., Xu, Y.F., Novel benzo-1, 2, 3-thiadiazole-7-carboxylate derivatives as plant activators and the development of their agricultural applications (2012) J. Agric Food Chem., 60, pp. 346-353; Zhan, P., Liu, X.Y., Li, Z.Y., Fang, Z.J., Li, Z., Wang, D.F., Pannecouque, C., Clercq, E.D., Novel 1, 2, 3-thiadiazole derivatives as HIV-1 NNRTIs with improved potency: Synthesis and preliminary SAR studies (2009) Bioorg. Med. Chem., 17, pp. 5920-5927; Liu, X.H., Pan, L., Weng, J.Q., Synthesis, structure, and biological activity of novel (oxdi/tri) azoles derivatives containing 1, 2, 3-thiadiazole or methyl moiety (2012) Mol Divers., 16, pp. 251-260; Liu, X.H., Wang, J.Q., Tan, C.X., Microwave synthesis and biological activity of hydrazone derivatives containing 1, 2, 3-thiadiazole (2011) Asian J. Chem., 23, pp. 4064-4066; Wang, H., Yang, Z.K., Fan, Z.J., Wu, Q.J., Zhang, J.H., Mi, N., Wang, S.X., Liu, F., Synthesis and insecticidal activity of N-tert-butyl-N, N'-diacylhydrazines containing 1, 2, 3-thiadiazoles (2011) J. Agric. Food Chem., 59, pp. 628-634; Sheldrick, G.M., SHELXS-97 (1997) Program for Solution of Crystal Structures, , University of Gottingen, Germany; Sheldrick, G.M., SHELXL-97 (1997) Program for Crystal Structure Refinement, , University of Gottingen, Germany; Wang, S.X., Fu, Y.F., Fan, Z.J., Mi, N., Zhang, H.K., Song, H.B., Belskaya, N.P., Bakulev, V.A., Synthesis, crystal structure, and biological activity of naphthalen-2-yl-4-methyl-1, 2, 3-thiadiazole-5-carboxylate (2011) Chin. J. Struct. Chem., 30, pp. 235-239; Fan, R.Z., Wang, D., Fan, Z.J., Wang, S.X., Hua, W.W., Hua, X.W., Ji, X.T., Song, H.B., (2012) Synthesis, Crystal Structure, and Biological Activity of N-((1-cyclohexyl-1H-trazol-5-yl) (5-methyl-1, 2, 3-thiadiazol-4yl) Methyl)-4-nitrobenzenamine, 31, pp. 803-808; Chen, X.M., Cai, J.W., (2003) Single-crystal Structural Analysis Principles and Practices, pp. 114-115. , Science Press: Beijing; Fan, Z.J., Shi, Z.G., Zhang, H.K., Liu, X.F., Bao, L.L., Ma, L., Zuo, X., Mi, N., Synthesis and biological activity evaluation of 1, 2, 3-thiadiazole derivatives as potential elicitors with highly systemic acquired resistance (2009) Agric. Food Chem., 57, pp. 4279-4286
Correspondence Address Fan, Z.-J.; State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China; email: fanzj@nankai.edu.cn
Language of Original Document English
Abbreviated Source Title Jiegou Huaxue
Source Scopus