a (School of Pharmaceutical and Chemical Engineering,Chengxian College, Southeast University, Nanjing 210088, China)
b (College of Food Science and Light Industry,Nanjing Technical University, Nanjing 211816, China)
c (Nanjing Sanhome Pharmaceutical Co Ltd., Nanjing 210018, China)
Comparison of Fungicidal Difference of Two Arylpyrazoles Based on the Crystal Structures, Density Functional Theory Calculation and Molecular Docking
LIU Yuan-Yuan;LI Yi;LV Kun-Zhi
a (School of Pharmaceutical and Chemical Engineering,Chengxian College, Southeast University, Nanjing 210088, China)
b (College of Food Science and Light Industry,Nanjing Technical University, Nanjing 211816, China)
c (Nanjing Sanhome Pharmaceutical Co Ltd., Nanjing 210018, China)
Abstract:Two arylpyrazoles I and II were synthesized and characterized by NMR and single-crystal X-ray diffraction. Compound I displayed 71.4% fungicidal inhibition rate against Rhizoctonia solani at 0.1 ppm, better than the control pyraclostrobin, whereas II had little activity. Their fungicidal difference was discussed from theoretic level based on the crystal structure, density functional theory (DFT) calculation and molecular docking. The B3LYP/6-31G** level was employed to explore the HOMO-LUMO energy gap and charge distribution. Molecular docking was performed on the probable target protein bc1-enzyme complex. DFT calculation and docking studies supported the in vitro findings.
基金资助:This project was supported by the Natural Science Foundation of Jiangsu Province (BK20161542), the Natural Science Foundation of the Higher Education Institutions of Jiangsu Province (17KJB150006), and Jiangsu Overseas Visiting Scholar Program for University Prominent Young & Middle-aged Teachers and Presidents (2017)
刘媛媛;李壹;吕坤志. 基于晶体结构、密度泛函理论计算和分子对接技术的两种芳基吡唑衍生物杀菌效果比较[J]. 结构化学, 2019, 38(11): 1845-1856.
LIU Yuan-Yuan;LI Yi;LV Kun-Zhi. Comparison of Fungicidal Difference of Two Arylpyrazoles Based on the Crystal Structures, Density Functional Theory Calculation and Molecular Docking. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2019, 38(11): 1845-1856.
REFERENCES
(1) Chen, L.; Zhu, Y.; Fan, Z.; Guo, X.; Zhang, Z.; Xu, J.; Song, Y.; Yurievich, M. Y.; Belskaya, N. P.; Bakulev, V. A. Synthesis of 1,2,3-thiadiazole and thiazole-based strobilurins as potent fungicide candidates. J. Agric. Food Chem. 2017, 65, 745751.
(2) Liu, X.; Chen, X.; Wang, H.; Yang, T.; Ye, Q.; Ding, X. Dynamic characteristics of the novel strobilurin fungicide SYP-3343 in aerobic soils. J. Agric. Food Chem. 2014, 62, 33433347.
(3) Herms, S.; Seehaus, K.; Koehle, H.; Conrath, U. A strobilurin fungicide enhances the resistance of tobacco against tobacco mosaic virus and Pseudomonas syringae pv tabaci. Plant Physiol. 2002, 130, 120127.
(4) Mercader, J. V.; Suarez-Pantaleon, C.; Agullo, C.; Abad-Somovilla, A.; Abad-Fuentes, A. Production and characterization of monoclonal antibodies specific to the strobilurin pesticide pyraclostrobin. J. Agric. Food Chem. 2008, 56, 76827690.
(5) Sauter, H.; Steglich, W.; Anke, T. Strobilurins: evolution of a new class of active substances. Angew. Chem., Int. Ed. 1999, 38, 13281349.
(6) Herms, S.; Seehaus, K.; Koehle, H.; Conrath, U. A strobilurin fungicide enhances the resistance of tobacco against tobacco mosaic virus and pseudomonas syringae pvtabaci. Plant Physiol. 2002, 130, 120127.
(7) Li, Y.; Zhang, H.; Liu, J.; Yang, X.; Liu, Z. Stereoselective synthesis and antifungal activities of (E)-α-(methoxyimino)benzeneacetate derivatives containing 1,3,5-substituted pyrazole ring. J. Agric. Food Chem. 2006, 54, 36363640.
(8) Tu, S.; Xu, L.; Ye, L.; Wang, X.; Sha, Y.; Xiao, Z. Synthesis and fungicidal activities of novel indene-substituted oxime ether strobilurins. J. Agric. Food Chem. 2008, 56, 52475253.
(9) Hwang, I. C.; Kim, J. K.; Kim, H. H.; Kyung, S. H. Synthesis and SAR of methoxyiminoacetate and methoxyiminoacetamide derivatives as strobilurin analogues. Bull. Korean Chem. Soc. 2009, 30, 14751480.
(10) Zhao, P.; Liu, C.; Huang, W.; Wang, Y.; Yang, G. Synthesis and fungicidal evaluation of novel chalcone-based strobilurin analogues. J. Agric. Food Chem. 2007, 55, 56975700.
(11) Liu, Y.; Lv, K.; Li, Y.; Nan, Q.; Xu, J. Synthesis, fungicidal activity, structure-activity relationships (SARs) and density functional theory (DFT) studies of novel strobilurin analogues containing arylpyrazole rings. Sci. Rep. 2018, 8, 78227822.
(12) Lv, K.; Liu, Y.; Li, Y.; Xu, G.; Pan, X.; Li, F.; Chen, K.; Huang, B. Synthesis, fungicidal activity, structure-activity relationship and density functional theory studies of novel oxime ether derivatives containing 1-aryl-3-oxypyrazoles. J. Chem. Res. 2015, 39, 594600.
(13) Liu, Y.; Shi, H.; He, G.; Song, G.; Zhu, H. Synthesis, crystal structures, and fungicidal activity of novel 1,5-diaryl-3-(glucopyranosyloxy)-1H- pyrazoles. Helv. Chim. Acta 2012, 95, 16451656.
(14) Liu, Y.; He, G.; Kai, C.; Li, Y.; Zhu, H. Synthesis, crystal structure, and fungicidal activity of novel 1,5-diaryl-1H-pyrazol-3-oxy derivatives containing oxyacetic acid or oxy(2-thioxothiazolidin-3-yl)ethanone moieties. J. Heterocyclic Chem. 2012, 49, 13701375.
(15) Liu, Y.; He, G.; Chen, K.; Jin, Y.; Li, Y.; Zhu, H. DMF-Catalyzed direct and regioselective C-H functionalization: electrophilic/nucleophilic 4-halogenation of 3-oxypyrazoles. Eur. J. Org. Chem. 2011, 53235330.
(16) Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution. University of Göttingen, Germany 1997.
(17) Wilamowski, J.; Kulig, E.; Sepiol, J. J.; Burgiel, Z. J. Synthesis and in vitro antifungal activity of 1-amino-3,4-dialkylnaphthalene-2-carbonitriles and their analogues. Pest Manag. Sci. 2001, 57, 625632.
(18) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr. J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh PA 2003, Gaussian 03, Revision B.01.
(19) Lee, C.; Yang, W.; Parr, R. G. Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 1998, 37, 785789.
(20) Masoome, S.; Siyamak, S.; Liudmila, F.; Evgenij, D.; Mehrnoosh, K. DFT investigations (geometry optimization, UV/Vis, FT-IR, NMR, HOMO-LUMO, FMO, MEP, NBO, excited states) and the syntheses of new pyrimidine dyes. Chin. J. Struct. Chem. 2018, 37, 12011222.
(21) Clark, M.; Cramer, R. D.; Opdenbosh, N. V. Validation of the general purpose Tripos 5.2 force field. J. Comput. Chem. 1989, 10, 9821012.
(22) Wang, L.; Zhang, Y.; Lu, S.; Chen, Y.; Lu, T.; Liu, H. Molecular docking and 3D-QSAR studies on a series of fused heterocyclic amides as B-Raf inhibitors. Chin. J. Struct. Chem. 2017, 36, 15681585.
(23) Li, Y.; Liu, Y.; Xiong, Y.; Xiong, X. Crystal structures, vibrational spectra, and fungicidal activity of 1,5-diaryl-3-oxypyrazoles. Molecules 2014, 19, 13021316.
(24) Goodman, M.; Ganis, P.; Avitabile, G.; Migdal, S. Solid-state conformation of amide groups. Crystal structures of N-ethyl-N-p-nitrophenylcarbamoyl chloride and of N-phenylurethane. J. Am. Chem. Soc. 1971, 93, 33283331.
(25) Yao, S.; Lopes, V. H. C.; Fernández, F.; Garcı́a-Mera, X.; Morales, M.; Rodrı́guez-Borges, J. E.; Cordeiro, M. N. D. S. Synthesis and QSAR study of the anticancer activity of some novel indane carbocyclic nucleosides. Bioorg. Med. Chem. 2003, 11, 49995006.
(26) Al-Amiery, A. A.; Al-Bayati, R. I.; Saed, F. M.; Ali, W. B.; Kadhum, A. A. H.; Mohamad, A. B. Novel pyranopyrazoles: synthesis and theoretical studies. Molecules 2012, 17, 1037710389.
(27) Mansour, A. M. Coordination behavior of sulfamethazine drug towards Ru(III) and Pt(II) ions: synthesis, spectral, DFT, magnetic, electrochemical and biological activity studies. Inorg. Chim. Acta 2013, 394, 436445.
(28) Wang, Q.; Wang, H.; Wei, L.; Yang, S.; Chen, Y. Odd-even effects of electronic transport in carbon-chain-based molecular devices. J. Phys. Chem. C 2012, 116, 1170911713.