Citation: Huo Jing-Qian, Ma Liu-Yong, Zhang Zhe, Fan Zhi-Jin, Zhang Jin-Lin, Tetyana V. Beryozkina, Vasiliy A. Bakulev. Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives[J]. Chinese Chemical Letters, ;2016, 27(9): 1547-1550. doi: 10.1016/j.cclet.2016.06.019 shu

Synthesis and biological activity of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives

a.
College of Plant Protection, Agricultural University of Hebei, Baoding 071001, China
b.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
c.
Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Nankai University, Tianjin 300071, China
d.
The Ural Federal University Named after the First President of Russia B. N. Yeltsin, Ekaterinburg 620002, Russia

Received Date: 23 May 2016
Revised Date: 2 June 2016
Accepted Date: 7 June 2016
Available Online: 17 September 2016

Figures(2)

A series of novel N-(3-furan-2-yl-1-phenyl-1H-pyrazol-5-yl) amides derivatives were designed and synthesized. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS. All title compounds were evaluated for their herbicidal and antifungal activities. Preliminary bioassay results indicated that the title compounds showed good to moderate herbicidal activity at 1000 mg/L. Compound 6q presented the best activity against Digitaria sanguinalis (L) Scop., Amaranthus retroflexus L. and Arabidopsis thaliana with an inhibition degree of five. Compound 6d also showed an inhibition degree of five against D. sanguinalis. In addition, at 50 mg/L, most compounds exhibited good in vitro antifungal activity against Sclerotinia sclerotiorum, with compound 6c showing over 90% antifungal activity against S. sclerotiorum and Pellicularia sasakii.
- Amides derivative,
- Pyrazole,
- Furan,
- Synthesis,
- Herbicidal activity,
- Fungicidal activity
1. [1]
  Umina P.A., Weeks A.R., Roberts J.. The current status of pesticide resistance in Australian populations of the redlegged earth mite (Halotydeus destructor)[J]. Pest Manag. Sci., 2012,68:889-896. doi: 10.1002/ps.v68.6
2. [2]
  Norsworthy J.K., Ward S.M., Shaw D.R.. Reducing the risks of herbicide resistance:best management practices and recommendations[J]. Weed Sci., 2012,60:31-62. doi: 10.1614/WS-D-11-00155.1
3. [3]
  T. Van Leeuwen, W. Dermauw, M. Grbic, L. Tirry, R. Feyereisen, Spider mite control and resistance management:does a genome help? Pest Manag. Sci. 69(2013) 156-159.
4. [4]
  H. Sierotzki, G. Scalliet, A review of current knowledge of resistance aspects for the next-generation succinate dehydrogenase inhibitor fungicides, Phytopathology 103(2013) 880-887.
5. [5]
  Consortium R.E.X.. Heterogeneity of selection and the evolution of resistance[J]. Trends Ecol. Evol., 2013,28:110-118. doi: 10.1016/j.tree.2012.09.001
6. [6]
  J.W.H. Li, J.C. Vederas, Drug discovery and natural products:end of an era or an endless frontier? Science 325(2009) 161-165.
7. [7]
  Duke S.O., Dayan F.E., Rimando A.M.. Invited paper:chemicals from nature for weed management[J]. Weed Sci., 2002,50:138-151. doi: 10.1614/0043-1745(2002)050[0138:IPCFNF]2.0.CO;2
8. [8]
  Matsuura B.S., Keylor M.H., Li B.. A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities[J]. Angew. Chem. Int. Ed. Engl., 2015,54:3754-3757. doi: 10.1002/anie.201409773
9. [9]
  Wang T., Wu M.B., Chen Z.J.. Fragment-based drug discovery and molecular docking in drug design[J]. Curr. Pharm. Biotechnol., 2015,16:11-25. doi: 10.2174/1389201015666141122204532
10. [10]
  Gengenbacher M., Dick T.. Antibacterial drug discovery:doing it right[J]. Chem. Biol., 2015,22:5-6. doi: 10.1016/j.chembiol.2014.12.005
11. [11]
  Lindert S., Li M.X., Sykes B.D., McCammon J.A.. Computer-aided drug discovery approach finds calcium sensitizer of cardiac troponin[J]. Chem. Biol. Drug Des., 2015,85:99-106. doi: 10.1111/cbdd.12381
12. [12]
  Zhao B., Huo J.Q., Xing J.H.. Homologous modeling of transketolase AtTKL1 and its combination with a-terthienyl in Arabidopsis thaliana[J]. Chem. J. Chin. Univ., 2015,36:682-686.
13. [13]
  Murphy D.J., Walker D.A.. The properties of transketolase from photosynthetic tissue[J]. Planta, 1982,155:316-320. doi: 10.1007/BF00429458
14. [14]
  Villafranca J.J., Axelrod B.. Heptulose synthesis from nonphosphorylated aldoses and ketoses by spinach transketolase[J]. J. Biol. Chem., 1971,246:3126-3131.
15. [15]
  Henkes S., Sonnewald U., Badur R., Flachmann R., Stitt M.. A small decrease of plastid transketolase activity in antisense tobacco transformants has dramatic effects on photosynthesis and phenylpropanoid metabolism[J]. Plant Cell, 2001,13:535-551. doi: 10.1105/tpc.13.3.535
16. [16]
  J. Zheng, Y.Q. Liu, J.Y. Lv, Synthesis of methyl-furoate, Fine Chem. Intermed. 37(2007) 41-42, 45.
17. [17]
  Ma L.C., Yuan L.W., Xu C.Z.. An efficient synthesis of 2-aminothiophenes via the gewald reaction catalyzed by an N-methylpiperazine-functionalized polyacrylonitrile fiber[J]. Synthesis, 2013,45:45-52.
18. [18]
  Zhang J.L., Zhang L.H., Liu Y.C.. The herbicidal activity of mutant isolates from Botrytis cinerea[J]. Agric. Sci. China, 2006,5:622-628. doi: 10.1016/S1671-2927(06)60102-8
19. [19]
  Zhang L.H., Kang Z.H., Xu J., Xu W.C., Zhang J.L.. Isolation and structural indentification of herbicidal toxin fractions produced by Pythium aphanidermatum[J]. Agric. Sci. China, 2010,9:995-1000. doi: 10.1016/S1671-2927(09)60182-6
20. [20]
  Fan S.L., Zhang B., Gao L.Y.. Synthesis, antifungal activity and structureactivity relationship of 2-methoxycarbonyl/ethoxycarbonyl-4-fluorophenyl-1, 5-benzothiazepines[J]. Chem. J. Chin. Univ., 2014,35:2574-2583.
21. [21]
  Kondratieva M.L., Pepeleva A.V., Belskaia N.P.. A new synthetic method for the 2H-[J]. Tetrahedron, 2007,63:3042-3048. doi: 10.1016/j.tet.2007.01.059
22. [22]
  Efimov I., Bakulev V., Beliaev N.. Reactions of b-azolylenamines with sulfonyl azides as an approach to N-unsubstituted 1, 2, 3-triazoles and ethene-1, 2-diamines[J]. Eur. J. Org. Chem., 2014,2014:3684-3689. doi: 10.1002/ejoc.201402130
23. [23]
  T.V. Beryozkina, I.V. Efimov, W.M.F. Fabian, et al., Reactivity of 1, 2, 3-triazoles towards sulfonyl chlorides. a novel approach to 1-and 2-sulfonyl-4-azolyl-1, 2, 3-triazoles, Tetrahedron 71(2015) 6189-6195.
24. [24]
  Su W.N., Lin T.P., Cheng K.M.. An efficient one-pot synthesis of N-(1, 3-diphenyl-1H-pyrazol-5-yl) amides[J]. J. Heterocycl. Chem., 2010,47:831-837. doi: 10.1002/jhet.343
1. [1]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
2. [2]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
3. [3]
  Huiju Cao , Lei Shi . sp¹-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
4. [4]
  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
5. [5]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424
6. [6]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
7. [7]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
8. [8]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
9. [9]
  Xiaomeng Hu , Jie Yu , Lijie Sun , Linfeng Zhang , Wei Zhou , Dongpeng Yan , Xinrui Wang . Synthesis of an AVB@ZnTi-LDH composite with synergistically enhance UV blocking activity and high stability for potential application in sunscreen formulations. Chinese Chemical Letters, 2024, 35(11): 109466-. doi: 10.1016/j.cclet.2023.109466
10. [10]
  Bofei JIA , Zhihao LIU , Zongyuan GAO , Shuai ZHOU , Mengxiang WU , Qian ZHANG , Xiamei ZHANG , Shuzhong CHEN , Xiaohan YANG , Yahong LI . Cu(Ⅱ) and Cu(Ⅰ) complexes based on derivatives of imidazo[1,5-a]pyridine: Synthesis, structures, in situ metal-ligand reactions, and catalytic activity. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 1020-1036. doi: 10.11862/CJIC.20240317
11. [11]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
12. [12]
  Huashan Huang , Jingze Chen , Luyun Zhang , Hong Yan , Siqi Li , Fen-Er Chen . Oscillatory flow reactor facilitates fast photochemical Wolff rearrangement toward synthesis of α-substituted amides in flow. Chinese Chemical Letters, 2025, 36(2): 109992-. doi: 10.1016/j.cclet.2024.109992
13. [13]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
14. [14]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
15. [15]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
16. [16]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
17. [17]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
18. [18]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
19. [19]
  Xinyi Hu , Riguang Zhang , Zhao Jiang . Depositing the PtNi nanoparticles on niobium oxide to enhance the activity and CO-tolerance for alkaline methanol electrooxidation. Chinese Journal of Structural Chemistry, 2023, 42(11): 100157-100157. doi: 10.1016/j.cjsc.2023.100157
20. [20]
  Bin Dong , Ning Yu , Qiu-Yue Wang , Jing-Ke Ren , Xin-Yu Zhang , Zhi-Jie Zhang , Ruo-Yao Fan , Da-Peng Liu , Yong-Ming Chai . Double active sites promoting hydrogen evolution activity and stability of CoRuOH/Co₂P by rapid hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109221-. doi: 10.1016/j.cclet.2023.109221

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(705)
HTML views(5)

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