Citation: Hui-Dong REN, Kang-Ming LI, Yang-Jie YI, Man WANG, Jiao YE, Ai-Xi HU, Yun CHEN, Xiao-Ming OU, Jian-Ming LI. Synthesis, Crystal Structure and DFT Calculation of 2-Methoxyimino Phenylacetate Derivatives Containing 1, 3, 4-Oxadiazole Ring[J]. Chinese Journal of Structural Chemistry, ;2021, 40(12): 1647-1654. doi: 10.14102/j.cnki.0254-5861.2011-3292 shu

Synthesis, Crystal Structure and DFT Calculation of 2-Methoxyimino Phenylacetate Derivatives Containing 1, 3, 4-Oxadiazole Ring

Hui-Dong REN ^a ,
Kang-Ming LI ^a ,
Yang-Jie YI ^a ,
Man WANG ^a ,
Jiao YE ^a,, ,
Ai-Xi HU ^a,, ,
Yun CHEN ^a ,
Xiao-Ming OU ^b ,
Jian-Ming LI ^b

a.
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China
b.
National Pesticide Creation Engineering Technology Research Center, Hunan Research Institute of Chemical Industry Co., Ltd., Changsha 410007, China

Corresponding author: Jiao YE, yejiao@hnu.edu.cn Ai-Xi HU, axhu@hnu.edu.cn
Received Date: 2 June 2021
Accepted Date: 6 September 2021

Fund Project: the National Key R & D Program of China 2016YFD0300708

Figures(5)

Four novel 2-methoxyimino phenylacetate derivatives containing 1, 3, 4-oxadiazole ring were designed and synthesized from the key intermediate of Trifloxystrobin or Azoxystrobin via intermediate derivatization and active structure splicing. The chemical structures of the target compounds were confirmed by ¹H NMR, ¹³C NMR and elemental analysis. The crystal structure of methyl (E)-2-(methoxyimino)-2-(2-(((5-((4-methoxyphenoxy)methyl)-1, 3, 4-oxadiazol-2-yl)thio)methyl)phenyl)acetate (A1) was determined by single-crystal X-ray diffraction. Compound A1 belongs to triclinic system, space group P\begin{document}$ \overline 1 $\end{document} with two molecules in each unit cell. The benzene ring plane C(2)–C(3)–C(4)–C(5)–C(6)–C(7) and oxazole ring plane are nearly parallel with the dihedral angle of 6.4°. The benzene ring plane C(12)–C(13)–C(14)–C(15)–C(16)–C(17) and oxazole ring plane are not perpendicular with the dihedral angle of 49.4°. The crystal of compound A1 is stabilized by π-π stacking interactions. The fungicidal activities of the target compounds against four plant pathogenic fungi in vitro were tested, and some of them had good activities. The DFT calculation was carried out to study the structure-activity relationship of the title derivatives using Gasian 09 and Multiwfn 3.6.
- 2-methoxyimino phenylacetate derivatives,
- synthesis,
- crystal structure,
- fungicidal activities,
- DFT calculation
1. [1]
  Guo, Y.; Qu, L. L.; Wang, X. G.; Huang, M. X.; Jia, L.; Zhang, Y. B. Iodine-catalyzed oxidative cyclisation for the synthesis of sarisan analogues containing 1, 3, 4-oxadiazole as insecticidal agents. RSC. Adv. 2016, 6, 93505−93510. doi: 10.1039/C6RA22343E
2. [2]
  Li, X. W.; He, D. H. Synthesis, crystal structure and biological activity of 2-(anthracen-9-yl)-5-p-tolyl-1, 3, 4-oxadiazole. Chin. J. Struct. Chem. 2012, 31, 367−372.
3. [3]
  Zhou, Q.; Zheng, D. D.; Shi, Y. J.; Yao, W.; Qian, H. W.; Ding, Y.; Wei, Z. H.; Shen, A. B.; Feng, X.; Shi, J.; Dai, H. Synthesis and insecticidal activities of novel pyrazole oxime ethers containing an oxazole moiety. Chin. J. Org. Chem. 2018, 38, 3318−3325. doi: 10.6023/cjoc201807048
4. [4]
  Kapoor, A.; Dhiman, N. Synthesis and evaluation of 2-aryl substituted benzimidazole derivatives bearing 1, 3, 4-oxadiazole nucleus for antimicrobial activity. Der Pharmacia Sinica 2019, 8, 97−104.
5. [5]
  Sun, G. X.; Shi, Y. X.; Zhai, Z. W.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Liu, X. H.; Li, B. J. Synthesis, crystal structure and antifungal activity of 2-((2-fluorobenzyl)thio)-5-(pyridin-4-yl)-1, 3, 4-oxadiazole. Chin. J. Struct. Chem. 2016, 35, 1855−1859.
6. [6]
  Liu, J. C.; Wang, W. D.; He, H. W. Synthesis and fungicidal activity of 2, 5-substituted-1, 3, 4-oxadiazole derivatives. Chin. J. Org. Chem. 2014, 34, 1447−1451. doi: 10.6023/cjoc201403013
7. [7]
  Kalhor, M.; Dadras, A. Synthesis, characterization and herbicidal activities of new 1, 3, 4-oxadiazoles, 1, 3, 4-thiadiazoles and 1, 2, 4-triazoles derivatives bearing (R)-5-chloro-3-fluoro-2-phenoxypyridine. J. Heterocyclic Chem. 2013, 50, 220−224. doi: 10.1002/jhet.950
8. [8]
  Shi, Y. J.; Li, Y.; Fang, Y.; Chen, J.; Ye, L. Y.; Ge, S. S.; Dai, H. Synthesis and biological activity of novel cyanoacrylate containing 1, 3, 4-oxadiazole moiety. Chin. J. Org. Chem. 2016, 36, 2472−2478. doi: 10.6023/cjoc201605029
9. [9]
  Mo, Q. J.; Duan, W. G.; Li, X. R.; Huang, D. P.; Luo, Z. J. Synthesis and herbicidal activity of 2-substituted amino-5-dehydroabietyl-1, 3, 4-oxadiazole derivatives. Chin. J. Org. Chem. 2011, 31, 1114−1121.
10. [10]
  Huang, T. H.; Chen, H.; Chen, J.; Zhang, A. D. Syntheses, crystal structures, and biological activities of two 5-pyrimidinyl-1, 2, 4-oxadiazoles. Chin. J. Struct. Chem. 2014, 33, 1455−1459.
11. [11]
  Mochona, B.; Mazzio, E.; Gangapurum, M.; Mateeva, N.; Redda, K. K. Synthesis of some benzimidazole derivatives bearing 1, 3, 4-oxadiazole moiety as anticancer agents. Chem. Sci. Trans. 2015, 4, 534−540.
12. [12]
  Zheng, X. J.; Li, C. S.; Cui, M. Y.; Song, Z. W.; Bai, X. Q.; Liang, C. W.; Wang, H. Y.; Zhang, T. Y. Synthesis, biological evaluation of benzothiazole derivatives bearing a 1, 3, 4-oxadiazole moiety as potential anti-oxidant and anti-inflammatory agents. Bioorg. Med. Chem. Lett. 2020, 30, 127237. doi: 10.1016/j.bmcl.2020.127237
13. [13]
  Chen, T. B.; Wu, Y. Y. Research progress of oxadiazole electron transport materials. New Chem. Mater. 2009, 37, 15−17.
14. [14]
  Zhang, Z. M.; Li, G. W.; Ma, Y. G.; Wu, F.; Tian, W. J.; Shen, J. C. Synthesis of oxadiazole derivatives containing thiophene ring as electron transport materials in OEL devices. Chin. J. Org. Chem. 2000, 20, 529−532.
15. [15]
  Li, Y.; Liu, J.; Zhang, H. Q.; Yang, X. P.; Liu, Z. J. Stereoselective synthesis and fungicidal activities of (E)-α-(methoxyimino)-benzeneacetate derivatives containing 1, 3, 4-oxadiazole ring. Bioorg. Med. Chem. Lett. 2006, 16, 2278−2282. doi: 10.1016/j.bmcl.2006.01.026
16. [16]
  Li, P.; Yin, J.; Xu, W. M.; Wu, J.; He, M.; Hu, D. Y.; Yang, S.; Song, B. A. Synthesis, antibacterial activities, and 3D-QSAR of sulfone derivatives containing 1, 3, 4-oxadiazole moiety. Chem. Biol. Drug Des. 2013, 82, 546−556. doi: 10.1111/cbdd.12181
17. [17]
  Li, P.; Shi, L.; Yang, X.; Yang, L.; Chen, X. W.; Wu, F.; Shi, Q. C.; Xu, W. M.; He, M.; Hu, D. Y.; Song, B. A. Design, synthesis, and antibacterial activity against rice bacterial leaf blight and leaf streak of 2, 5-substituted-1, 3, 4-oxadiazole/thiadiazole sulfone derivative. Bioorg. Med. Chem. Lett. 2014, 24, 1677−1680. doi: 10.1016/j.bmcl.2014.02.060
18. [18]
  Su, S. H.; Zhou, X.; Liao, G. P.; Qi, P. Y.; Jin, L. H. Synthesis and antibacterial evaluation of new sulfone derivatives containing 2-aroxymethyl-1, 3, 4-oxadiazole/thiadiazole moiety. Molecules 2017, 22, 64.
19. [19]
  Wang, S. B.; Gan, X. H.; Wang, Y. J.; Li, S. Y.; Yi, C. F.; Chen, J. X.; He, F. C.; Yang, Y. Y.; Hu, D. Y.; Song, B. A. Novel 1, 3, 4-oxadiazole derivatives containing a cinnamic acid moiety as potential bactericide for rice bacterial diseases. Int. J. Mol. Sci. 2019, 20, 1020. doi: 10.3390/ijms20051020
20. [20]
  Hu, A. X.; Li, K. M.; Xie, W. X.; Ye, J.; Chen, J.; Xie, B. J.; Ren, H. D. A preparation method of trifloxystrobin and its intermediate. CN 108863845 A. 2018−11−23.
21. [21]
  Zhu, Z. L.; Zhang, R. H.; Yuan, L. L.; Ni, Y. M. A method of preparing trifloxystrobin. CN 1560027 A. 2005−01−05.
22. [22]
  Zhang, R. H.; Zhu, Z. L.; Li, Y. J. A high-yield synthesis process of trifloxystrobin. CN 1793115 A. 2006−06−28.
23. [23]
  Wang, X. B.; Yan, J. H.; Wang, M. Q.; Liu, M. H.; Zhang, J. P.; Chen, L. J.; Xue, W. Synthesis and three-dimensional quantitative structure-activity relationship study of quinazoline derivatives containing a 1, 3, 4-oxadiazole moiety as efficient inhibitors against Xanthomonas axonopodis pv. citri. Mol. Divers. 2018, 22, 791−802.
24. [24]
  Sheldrick, G. M. A short history of SHELXS. Acta. Cryst. 2008, A64, 112−122.
25. [25]
  Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution. University of Göttingen. Germany 1997.
26. [26]
  Song, B. A.; Chen, Y. Z.; Chen, J. X.; Wang, Y. J.; Wang, Z. Z.; Zhou, D. G.; Gan, X. H. Styryl-containing 1, 3, 4-oxadiazole sulfide compound, preparation method and application thereof. CN 106674147 A. 2017−05−17.
27. [27]
  Liu, A. P.; Yu, W. Q.; Liu, M. H.; Bai, J. J.; Liu, W. D.; Liu, X. P.; Pei, H.; Hu, L.; Huang, M. Z.; Wang, X. G. Synthesis and insecticidal activity of novel nitropyridyl-based dichloropropene ethers. J. Agric. Food Chem. 2015, 63, 7469−7475.
28. [28]
  Abu-Awwad, F.; Politzer, P. Variation of parameters in Becke-3 hybrid exchange correlation functional. J. Comput. Chem. 2015, 21, 227−238.
29. [29]
  Lee, C.; Wang, W.; Parr, R. G. Development of the Colle-Salvetti correlation energy formula into a functional of the electron density. Phys. Rev. B 1988, 37, 785−789.
30. [30]
  Lu, T.; Chen, F. W. Multiwfn: a multifunctional wavefunction analyzer. J. Comput. Chem. 2012, 33, 580−592.
31. [31]
  Lu, T.; Chen, F. W. Quantitative analysis of molecular surface based on improved marching tetrahedra algorithm. J. Mol. Graph. Model. 2012, 38, 314−323.
32. [32]
  Humphrey, W.; Dalke, A.; Schulten, K. VMD: visual molecular dynamics. J. Mol. Graph. 1996, 14, 33−38.
33. [33]
  Guo, H.; Han, J.; Pang, M. L.; Ma, Y. X.; Meng, J. B. Synthesis and characterization of acrylate group bridged γ-substituted β-diketopyrazole and isoxazole derivatives. Chem. J. Chinese Universities 2005, 26, 1845−1848.
34. [34]
  Zhang, Y.; Shi, W. F. Synthesis and photopolymerization properties of self-initiated photopolymerized acrylate oligomers. Chem. J. Chinese Universities 2012, 33, 635−639.
35. [35]
  Xiao, J. C.; Wu, Q.; Lei, Y.; Sun, J. R.; Jiang, F.; Xu, Y.; Xu, X. D.; Li, T. Y. Synthesis, single-crystal X-ray structure, theoretical studies of triple-{Mn-III-Schiff-base}-decorated molybdate. Crystals 2019, 9, 657.
36. [36]
  Janiak, C. A critical account on π-π stacking in metal complexes with aromatic nitrogen-containing ligands. J. Chem. Soc., Dalton Trans. 2000, 21, 3885−3896.
37. [37]
  Wang, B. L.; Shi, Y. X.; Zhang, S. J.; Ma, Y.; Wang, H. X.; Zhang, L. Y.; Wei, W.; Liu, X. H.; Li, Y. H.; Li, Z. M.; Li, B. J. Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties. Eur. J. Med. Chem. 2016, 117, 167−178.
38. [38]
  Karelson, M.; Lobanov, V. S. Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev. 1996, 96, 1027−1043.
39. [39]
  Farag, A. M.; Fahim, A. M. Synthesis, biological evaluation and DFT calculation of novel pyrazole and pyrimidine derivatives. J. Mol. Struct. 2019, 1179, 304−314.
40. [40]
  Du, Q. S.; Wang, C. H.; Wang, Y. T.; Huang, R. B. Empirical and accurate method for the three dimensional electrostatic potential (EM-ESP) of biomolecules. J. Phys. Chem. B 2010, 114, 4351−4357.
41. [41]
  Murray, J. S.; Politzer, P. The electrostatic potential: an overview. Wires Comput. Mol. Sci. 2011, 1, 153−163.
1. [1]
  Jing Wang , Zhongliao Wang , Jinfeng Zhang , Kai Dai . Single-layer crystalline triazine-based organic framework photocatalysts with different linking groups for H2O2 production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100202-100202. doi: 10.1016/j.cjsc.2023.100202
2. [2]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
3. [3]
  Ya-Nan Yang , Zi-Sheng Li , Sourav Mondal , Lei Qiao , Cui-Cui Wang , Wen-Juan Tian , Zhong-Ming Sun , John E. McGrady . Metal-metal bonds in Zintl clusters: Synthesis, structure and bonding in [Fe₂Sn₄Bi₈]^3– and [Cr₂Sb₁₂]^3–. Chinese Chemical Letters, 2024, 35(8): 109048-. doi: 10.1016/j.cclet.2023.109048
4. [4]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
5. [5]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
6. [6]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
7. [7]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
8. [8]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
9. [9]
  Haibin Yang , Duowen Ma , Yang Li , Qinghe Zhao , Feng Pan , Shisheng Zheng , Zirui Lou . Mo doped Ru-based cluster to promote alkaline hydrogen evolution with ultra-low Ru loading. Chinese Journal of Structural Chemistry, 2023, 42(11): 100031-100031. doi: 10.1016/j.cjsc.2023.100031
10. [10]
  Guangchang Yang , Shenglong Yang , Jinlian Yu , Yishun Xie , Chunlei Tan , Feiyan Lai , Qianqian Jin , Hongqiang Wang , Xiaohui Zhang . Regulating local chemical environment in O3-type layered sodium oxides by dual-site Mg²⁺/B³⁺ substitution achieves durable and high-rate cathode. Chinese Chemical Letters, 2024, 35(9): 109722-. doi: 10.1016/j.cclet.2024.109722
11. [11]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
12. [12]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
13. [13]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
14. [14]
  Linshan Peng , Qihang Peng , Tianxiang Jin , Zhirong Liu , Yong Qian . Highly efficient capture of thorium ion by citric acid-modified chitosan gels from aqueous solution. Chinese Chemical Letters, 2024, 35(5): 108891-. doi: 10.1016/j.cclet.2023.108891
15. [15]
  Lian Sun , Honglei Wang , Ming Ma , Tingting Cao , Leilei Zhang , Xingui Zhou . Shape and composition evolution of Pt and Pt₃M nanocrystals under HCl chemical etching. Chinese Chemical Letters, 2024, 35(9): 109188-. doi: 10.1016/j.cclet.2023.109188
16. [16]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
17. [17]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
18. [18]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
19. [19]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
20. [20]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(223)
HTML views(1)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142