Citation: YUAN Lin, LI Zhongyan, JIA Guokai, ZHANG Min, YUAN Xianyou. Synthesis and Biological Activity of Perimidine Derivatives[J]. Chinese Journal of Applied Chemistry, ;2017, 34(6): 685-692. doi: 10.11944/j.issn.1000-0518.2017.06.160393 shu

Synthesis and Biological Activity of Perimidine Derivatives

Department of Biology and Chemistry, Hu'nan University of Science and Engineering, Yongzhou, Hu'nan 425199, China

Corresponding author: LI Zhongyan, lizhongyandongdong@126.com
Received Date: 28 September 2016
Revised Date: 15 December 2016
Accepted Date: 14 February 2017

Fund Project: the Scientific Research Fund of Hu′nan University of Science and Engineering 16XKY063the Scientific Research Fund of Hu′nan Provincial Education Department 16B104the Opening Project of Key Laboratory of Comprehensive Utilization of Advantage Plants Resources in Hu′nan South XNZW16C01the Natural Science Foundation of Hu′nan Province of China 2017JJ3093

Figures(3)

Perimidine is a multi-nuclear N-heterocyclic compound, which plays an important role in industrial and biological fields. Perimidines have been drawn extensive examinations from many researchers for a long time due to the nitrogen heterocyclic ring. Here, a series of perimidine derivatives(4a~4g and 6) was synthesized through 1, 8-diaminonaphthalene and aldehydes. The products were characterized by infrared spectroscopy(IR), proton or carbon nuclear magnetic resonance(¹H NMR, ¹³C NMR), high resolution mass spectrometry(HRMS). Compounds 4a and 6 were investigated by single-crystal X-ray diffraction. X-ray analysis reveals that both of crystals of 4a and 6 are made up of monoclinic unit cells with space group P2₁/n. In addition, the biological activity assay was carried out. The results show that perimidine derivatives have a diverse range of biological activities against the fungi, which indicates that perimidine derivatives have great potential applications in antibacterial fields in the future. And test data indicate that there is no obvious regulation between fungicidal activity and the different substituents on the benzene ring.
- perimidine,
- synthesis,
- crystal structure,
- biological activity
1. [1]
  Hashim J A, Kezhal M S. Synthesis, Characterization and Biological Activity of 2-Aryl-2, 3-dihydro-1H-Perimidine[J]. Res Pharm Biotechnol, 2014(1):1-6.
2. [2]
  Jung I G, Son S U, Park K H. Synthesis of Novel Pd-NCN Pincer Complexes Having Additional Nitrogen Coordination Sites and Their Application as Catalysts for the Heck Reaction[J]. Organometallics, 2003(23):4715-4720.
3. [3]
  Vanden E J J, Delfosse F, Mayence A. Old Reagents, New Results-aromatization of Hantzsch 1, 4-Dihydropyridines with Manganese-dioxide and 2, 3-Dichloro-5, 6-dicyano-1, 4-Benzoquinone[J]. Tetrahedron, 1995(20):5813-5818.
4. [4]
  Hendrickson J B, Hussoin M S. Seeking the Ideal Dehydrating Reagent[J]. J Org Chem, 1987(18):4137-4139.
5. [5]
  Deady L W, Rodemann T J. Synthesis of Perimidine and Fused Perimidine Derivatives from Reaction of 1, 8-Naphthalenediamine with an Iminoisocoumarin[J]. Heterocycl Chem, 1998(6):1417-1419.
6. [6]
  Mueller-Westerhoff U T, Vance B, Dong I Y. The Synthesis of Dithiolene Dyes with Strong Near-IR Absorption[J]. Tetrahedron, 1991(6):909-932.
7. [7]
  Starshikov M, Pozharskii F T. Synthesis of 2-(5-Halogeno-2-furyl)-2, 3-Dihydroperimidines[J]. Chem Heterocycl Compd, 1973(7):922-924.
8. [8]
  Przemyslaw M, Anu C, Christopher R M. Optical Properties of Spiroconjugated Charge-transfer Dyes[J]. J Am Chem Soc, 1996(6):1471-1481.
9. [9]
  Starshikov N M, Pozharskii A F. Heterocyclic Analogs of Pleiadiene[J]. Chem Heterocycl Compd, 1978(10):1413-1417.
10. [10]
  Sokolov V I, Pozharskii A F, Kashparov I S. Heterocyclic Analogs of Pleiadiene[J]. Chem Heterocycl Compd, 1974(4):558-561.
11. [11]
  Bu X, Deady L W, Finlay G. J. Synthesis and Cytotoxic Activity of 7-Oxo-7H-dibenz[f, ij]isoquinoline and 7-Oxo-7H-benzo[e]perimidine Derivatives[J]. J Med Chem, 2001(12):2004-2014.
12. [12]
  Gong X W, Li X, Li W L. Synthesis and Crystal Structure of (E)-4-(Benzyloxy)-2-(cinnamoyl-oxy)-N, N, N-trimethyl-4-oxobutan-1-Aminium Chloride as a Double-prodrug[J]. Chinese J Struct Chem, 2008(2):177-182.
13. [13]
  Ye J, Sun X X, Qiu S Y. Synthesis, Crystal Structure and Fungicidal Activity of N-(4-tert-buty)-5-(1, 2, 4-triazol-1-yl)thiaz-ol-2-yl) Propionamide[J]. Chinese J Struct Chem, 2014(3):429-433.
14. [14]
  Fu C R, Pei J, Ning Y. Synthesis and Insecticidal Activities of Novel Pyrazole Oxime Ether Derivatives with Different Substituted Pyridyl Rings[J]. Pest Manage Sci, 2013(8):1207-1214.
15. [15]
  Mobinikhaledi A, Sasani F, Hamta A. Molecular Iodine Catalyzed Synthesis of Some Biologically Active Dihydroperimidines[J]. Bulg Chem Commun, 2013(3):353-356.
16. [16]
  Yuan L, Li Z Y, Zhang M. Synthesis, Crystal Structure and Anti-fungal Activity of 2-(4-Chlor-ophenyl)-1, 3-dimethyl-[JP]2, 3-dihydro-1H-Perimidine[J]. Chinese J Struct Chem, 2016(8):1181-1185.
17. [17]
  Sokolov V I, Ardashev B I, Kashparov I S. Heterocyclic Analogs of Pleiadiene X.Reaction of 2-Substituted Quaternary Perimidinium Salts with Alkali[J]. Khim Geterosikl Soedin, 1973(6):782-784.
18. [18]
  Sheldrick G M. SHELXS-97. Program for Solution of Crystal Structures[CP]. University of Gottingen, Germany, 1997.
19. [19]
  Sheldrick G M. SHELXL-97. Program for Crystal Structure Refinement[CP]. University of Gottingen, Germany, 1997.
20. [20]
  Fan Z J, Yang Z K, Zhang H K. Synthesis, Crystal Structure, and Biological Activity of 4-Methyl-1, 2, 3-thiadiazole Containing 1, 2, 4-Triazolo(3, 4-b)(1, 3, 4) thiadiazoles[J]. J Agric Food Chem, 2010(5):2630-2636.
21. [21]
  Li F Y, Zhu Y J, Fan Z J. Synthesis, Crystal Structure and Biological Activity of 2-(1-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl)piperidin-4-yl)-N-isopropyl-1, 3-thiazole-4-Carboxamide[J]. Chinese J Struct Chem, 2015(5):659-666.
22. [22]
  Fan Z J, Shi Z G, Zhang H K. Synthesis and Biological Activity Evaluation of 1, 2, 3-Thiadiazole Derivatives as Potential Elicitors with Highly Systemic Acquired Resistance[J]. J Agric Food Chem, 2009(10):4279-4286.
1. [1]
  Lifang HE , Yaoze LUO , Qiying SHI , Jianxin TANG , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and properties of hydrated tricyclohexyltin theophylline-7-acetic acid complex. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 632-640. doi: 10.11862/CJIC.20250244
2. [2]
  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
3. [3]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
4. [4]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
5. [5]
  Wenya DING , Fangfei XU , Jiayu GU , Xinran CHEN , Kai CHEN . Synthesis and crystal structure of three cucurbit[6]uril-cadmium supramolecular assemblies. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 808-816. doi: 10.11862/CJIC.20260012
6. [6]
  Yingyue ZHANG , Liuqing KANG , Yating YANG , Xiaofen GUAN , Wenmin WANG . Crystal structure and antibacterial activity of two Gd₂ complexes based on polydentate Schiff-base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1867-1877. doi: 10.11862/CJIC.20250100
7. [7]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150
8. [8]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
9. [9]
  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
10. [10]
  Yinxia SUN , Liping LIU , Xue BAI , Yu SUN , Wanhong SUN , Zhepeng DENG , Jianghai CHEN , Jianjun WANG , Li XU , Shuzhen ZHANG . Synthesis and crystal structures of Co(Ⅱ)/Cu(Ⅱ) coordination polymers based on solvent and ligand concentration regulation strategy. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 340-354. doi: 10.11862/CJIC.20250226
11. [11]
  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
12. [12]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
13. [13]
  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
14. [14]
  Chengyu JIANG , Xufeng LIU . Synthesis, structural characterization, electrocatalytic proton reduction, and fungicidal activity of thiazole-containing di-iron complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 355-364. doi: 10.11862/CJIC.20250253
15. [15]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
16. [16]
  Jing FENG , Renshu WANG , Hu WANG , Hailong LIU . Co(Ⅱ) and Ni(Ⅱ) complexes of 3,3-diphenylpropionic acid and 2,2′-dipyridylamine: Structures and biological activities. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 617-631. doi: 10.11862/CJIC.20250265
17. [17]
  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
18. [18]
  Ruiyan CHEN , Yanping HE , Jian ZHANG . Synthesis and third-order nonlinear optical property of Ti₄L₆ cage-based metal-organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2149-2156. doi: 10.11862/CJIC.20250177
19. [19]
  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
20. [20]
  Fan LIU , Xiaoli CHEN , Jing REN , Yantao LEI , Huali CUI , Hua YANG , Jijiang WANG . Highly sensitive and multi-response Zn-MOF fluorescence sensor: Design, synthesis, and detection of 4-nitrophenol, Cu²⁺, and pyrimethanil. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 872-882. doi: 10.11862/CJIC.20250287

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(811)
HTML views(94)

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