Citation: LIU Jianchao, REN Qingyun, HE Hongwu. Synthesis and Biological Activity of Pyrazolo[4', 3':5, 6]pyrano[2, 3-d]pyrimidine Derivatives[J]. Chinese Journal of Applied Chemistry, ;2017, 34(11): 1279-1286. doi: 10.11944/j.issn.1000-0518.2017.11.160502 shu

Synthesis and Biological Activity of Pyrazolo[4', 3':5, 6]pyrano[2, 3-d]pyrimidine Derivatives

a.
College of Chemistry, Central China Normal University, Wuhan, 430079, China
b.
Anti-infection Innovation Department, New Drug Research Institute, HEC, Dongguan, Guangdong 523871, China

Corresponding author: HE Hongwu, he1208@mail.ccnu.edu.cn
Received Date: 9 December 2016
Revised Date: 20 January 2017
Accepted Date: 24 February 2017

Fund Project: Supported by the National Natural Science Fundation of China(No.21172090, No.31000867), the Program for Changjiang Scholars and Innovatives Research Team in University(No.IRT0953)the Program for Changjiang Scholars and Innovatives Research Team in University IRT0953the National Natural Science Fundation of China 21172090the National Natural Science Fundation of China 31000867

Figures(2)

A series of new 2-substituted-3, 8-diphenyl-5-aryl-6-methyl-5, 8-dihydropyrazolo[4', 3':5, 6]pyrano[2, 3-d]pyrimidine derivatives was designed and synthesized via tandem aza-Wittig reaction. The structures of target compounds were confirmed by ¹H NMR, IR spectra and elemental analysis. The structure of 2-dipropylamino-3, 8-diphenyl-5-(4-methylphenyl)-6-methyl-5, 8-dihydropyrazolo[4', 3':5, 6]pyrano[2, 3-d]pyrimidin-4(3H)-one was determined by single crystal X-ray diffraction. The results of preliminary bioassay indicate that some compounds possess good inhibition activities against Botrytis cinereapers at a dosage of 5.0×10^-5 g/mL, and the inhibition rates against Botrytis cinereapers are above 90%. Target compounds possess no insecticidal activity against Nilaparvatalegen, but show obvious insecticidal activity against Mythimaseparata, and the inhibihition rates against Mythimaseparata are above 60%.
- Aza-Wittig reaction,
- pyrazolopyrimidine,
- pyranopyrimidine,
- biological activity
1. [1]
  Haraguchi K, Kubota Y, Tanaka H. Ring Opening of Nucleoside 1', 2'-Epoxides with Organoaluminum Reagents:Stereoselective Entry to Ribonucleosides Branched at the Anomeric Position[J]. J Org Chem, 2004,69(6):1831-1836. doi: 10.1021/jo030262u
2. [2]
  Cushman M, Sambaiah T, Jin G. Design, Synthesis, and Evaluation of 9-D-Ribitylamino-1, 3, 7, 9-Tetrahydro-2, 6, 8-Purinetriones Bearing Alkyl Phosphate and α, α-Difluorophosphonate Substituents as Inhibitors of Riboflavin Synthase and Lumazine Synthase[J]. J Org Chem, 2004,69(3):601-612. doi: 10.1021/jo030278k
3. [3]
  Depecker G, Patino N, Giorgio C D. Cyclic PNA-based Compound Directed Against HIV-1 TAR RNA:Modelling, Liquid-phase Synthesis and TAR Binding[J]. Org Biomol Chem, 2004,2(1):74-79. doi: 10.1039/b311775h
4. [4]
  Wnuk S F, Lewandowska E, Companioni D R. Synthesis and Cytotoxicity of 9-(2-Deoxy-2-Alkyldithio-β-D-Arabinofuranosyl)purine Nucleosides Which are Stable Precursors to Potential Mechanistic Probes of Ribonucleotide Reductases[J]. Org Biomol Chem, 2004,2(1):120-126. doi: 10.1039/B311504F
5. [5]
  Aly H M, Kamal M M. Efficient One-pot Preparation of Novel Fused Chromeno[2, 3-d]pyrimidine and Pyrano[2, 3-d] Pyrimidine Derivatives[J]. Eur J Med Chem, 2012,47(1):18-23.
6. [6]
  Saundne A R, Vijaykumar K, Vaijinath A V. Synthesis of Novel 2-Amino-4-(5'-Substituted 2'-Phenyl-2H-Indol-3'-yl)-6-Aryl-4H-Pyran-3-Carbonitrile Derivatives as Antimicrobial and Antioxidant Agents[J]. Bioorg Med Chem Lett, 2013,23(7):1978-1984. doi: 10.1016/j.bmcl.2013.02.036
7. [7]
  Clinch K, Watt D K, Dixon R A. Synthesis of Cyclic Pyranopterin Monophosphate, A Biosynthetic Intermediate in the Molybdenum Cofactor Pathway[J]. J Med Chem, 2012,56(5):1730-1738.
8. [8]
  Kamdar N R, Haveliwala D D, Mistry P T. Design, Synthesis and in vitro Evaluation of Antitubercular and Antimicrobial Activity of some Novel Pyranopyrimidines[J]. Eur J Med Chem, 2010,45(11):5056-5063. doi: 10.1016/j.ejmech.2010.08.014
9. [9]
  Kazemi-Red R, Azizian J, Kefayati H. Electrogenerated Acetonnitrile Anions/tetrabutylammonium Cations:An Effective Catalytic System for the Synthesis of Novel Chromeno[3', 4':5, 6] Pyrano[2, 3-d]Pyrimidines[J]. Tetrahedron Lett, 2014,55(50):6887-6890. doi: 10.1016/j.tetlet.2014.10.099
10. [10]
  CHEN Qingfang, XU Xingyou, WANG Qifa. One-pot Synthesis of Pyrano[2, 3-d]Pyrimidine Derivatives in Aqueous Media under Microwave Irradiatio[J]. Chinese J Appl Chem, 2010,27(6):673-676.
11. [11]
  LIU Jianchao, LIANG Ying, HE Hongwu. Synthesis and Biological Activity of 6-Alkylamino(oxy)-3-Methylthio-1H-Pyrazolo[3, 4-d]Pyrimidin-4(5H)-One Derivatives[J]. Chinese J Appl Chem, 2014,31(8):922-927.
12. [12]
  DAI Guiyuan, SHI Daqing, ZHOU Longhu. Knoevenagel Condensation Catalyzed by Potassium Fluoride/Alumina[J]. Chinese J Appl Chem, 1995,12(3):103-104.
13. [13]
  SHI Daqing, ZHANG Shu, ZHUANG Qiya. Michael Addition of 3-Methyl-2-pyrazolin-5-one to α, β-Unsaturated Ketones in Water[J]. Chinese J Org Chem, 2003,23(9):1036-1038.
14. [14]
  Muthusamy S, Babu S A, Gunanath C. 1, 8-Diazabicyclo[5.4.0] Undec-7-Ene(DBU):A Powerful Catalyst for the Michael Addition Reaction of β-Ketoesters to Acrylates and Enones[J]. Synth Commu, 2002,32(21):3247-3254. doi: 10.1081/SCC-120014028
15. [15]
  Sheldrick G M. SHELXS97 and SHELXL97[P]. Germanry:University of Gottingen, 1997.
1. [1]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
2. [2]
  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
3. [3]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
4. [4]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
5. [5]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
6. [6]
  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
7. [7]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
8. [8]
  Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
9. [9]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
10. [10]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
11. [11]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
12. [12]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
13. [13]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
14. [14]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(12): 0-0.
15. [15]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
16. [16]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
17. [17]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
18. [18]
  Zhibei Qu , Changxin Wang , Lei Li , Jiaze Li , Jun Zhang . Organoid-on-a-Chip for Drug Screening and the Inherent Biochemistry Principles. University Chemistry, 2024, 39(7): 278-286. doi: 10.3866/PKU.DXHX202311039
19. [19]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
20. [20]
  Yang Liu , Peng Chen , Lei Liu . Chemistry “101 Plan”: Design and Construction of Chemical Biology Textbook. University Chemistry, 2024, 39(10): 45-51. doi: 10.12461/PKU.DXHX202407085

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(273)
HTML views(69)

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