Citation: HUANG Zhining, ZHENG Manyi, MIAO Fangxiao, YU Jingqi, LI Shanhua, LI Funan, QU Ning. Synthesis and Anti-hepatoma Activities of N-(Piperidin-4-yl)benzamide Derivatives[J]. Chinese Journal of Applied Chemistry, ;2016, 33(6): 661-667. doi: 10.11944/j.issn.1000-0518.2016.06.150358 shu

Synthesis and Anti-hepatoma Activities of N-(Piperidin-4-yl)benzamide Derivatives

  • Corresponding author: QU Ning, 
  • Received Date: 10 October 2015
    Available Online: 23 December 2015

    Fund Project:

  • Six benzamide derivatives were synthesized from 4-hydroxybenzoic acid via alkylation, hydrolysis and condensation reactions. The structure was confirmed by 1H NMR, 13C NMR and MS. The antitumor activity of all the newly synthesized compounds was evaluated on the in vitro growth of HepG2 cell line using sorafeinb as positive control. The anti-hepatoma biological activity in vitro of N-(1-(methylsulfonyl)piperidin-4-yl)-4-phenoxybenzamide is better than that of sorafeinb with an IC50 value of 8.42 μmol/L. The results show that the derivatives of N-(piperidin-4-yl)-4-phenoxybenzamide have good anti-hepatoma activity.
  • 加载中
    1. [1]

      [1] CHEN Wanqing,ZHANG Siwei,ZENG Hongmei,et al.Report of Cancer Incidence and Mortality in China 2010[J].China Cancer,2014,23(1):1-10(in Chinese).陈万青,张思维,曾红梅,等.中国2010年恶性肿瘤发病与死亡[J].中国肿瘤,2014,23(1):1-10.

    2. [2]

      [2] CHEN Jianguo.Trends in the Incidence of Liver Cancer and Its Primary Prevention in China[J].J Clin Hepatol,2012,28(4):256-260(in Chinese).陈建国.中国肝癌发病趋势和一级预防[J].临床肝胆病杂志,2012,28(4):256-260.

    3. [3]

      [3] Ueno M,Uchiyama K,Ozawa S,et al.Adjuvant Chemolipiodolization Reduces Early Recurrence Derived from Intrahepatic Metastasis of Hepatocellular Carcinoma after Hepatectomy[J].Ann Surg Oncol,2011,18(13):3624-3631.

    4. [4]

      [4] WANG Fang,FU Liwu.Research Advances in Sorafenib:A Multiple Targeted Anti-tumor Agent[J].Chinese Pharmacol Bull,2008,24(8):1117-1120(in Chinese).王芳,符立梧.多靶点抗肿瘤新药索拉非尼的研究进展[J].中国药理学通报,2008,24(8):1117-1120.

    5. [5]

      [5] Scott W,Christopher C,Mark L,et al.Discovery and Development of Sorafenib:A Multikinase Inhibitor for Treating Cancer[J].Nat Rev Drug Discov,2006,5(10):835-844.

    6. [6]

      [6] Yang S M,Huang Z N,Zhou Z S,et al.Structure-based Design,Structure-Activity Relationship Analysis,and Antitumor Activity of Diaryl Ether Derivatives[J].Arch Pharm Res,2015,38(10):1761-1773.

    7. [7]

      [7] Hou J,Zhao W,Huang Z N,et al.Evaluation of Novel N-(Piperidin-4-yl) benzamide Derivativesas Potential Cell Cycle Inhibitors in HepG2 Cells[J].Chem Biol Drug Des,2015,86(2):223-231.

    8. [8]

      [8] Lobb K,Hipskind P,Aikins J,et al.Acyl Sulfonamide Anti-Proliferatives:Benzene Substituent Structure-Activity Relationships for a Novel Class of Antitumor Agents[J].J Med Chem,2004,47(22):5367-5380.

    9. [9]

      [9] Bouchain G,Leit S,Frechette S,et al.Development of Potential Antitumor Agents.Synthesis and Biological Evaluation of a New Set of Sulfonamide Derivatives as Histone Deacetylase Inhibitors[J].J Med Chem,2003,46(5):820-830.

    10. [10]

      [10] LIU Fei,LIU Nan,HE Ling.Synthesis and Antitumor Activities of Sulfonyl Amidine Derivatives[J].Chinese J Synth Chem,2014,22(4):440-443(in Chinese).刘菲,刘楠,何菱.磺酰脒衍生物的合成及其抗肿瘤活性[J].合成化学,2014,22(4):440-443.

    11. [11]

      [11] Yang Y,Wang Z,Yang J,et al.Design,Synthesis and Evaluation of Novel Molecules with a Diphenyl Ether Nucleus as Potential Antitubercular Agents[J].Bioorg Med Chem Lett,2012,22(2):954-957.

    12. [12]

      [12] Gamet-Payrastre L,Li P,Lumeau S,et al.Sulforaphane,a Naturally Occurring Isothiocyanate,Induces Cell Cycle Arrest and Apoptosis in HT29 Human Colon Cancer Cells[J].Cancer Res,2000,60(5):1426-1433.

  • 加载中
    1. [1]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin 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

    2. [2]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng 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

    3. [3]

      Shiyi WANGChaolong CHENXiangjian KONGLansun ZHENGLasheng LONG . Polynuclear lanthanide compound [Ce4Ce6(μ3-O)4(μ4-O)4(acac)14(CH3O)6]·2CH3OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342

    4. [4]

      Xin MAYa SUNNa SUNQian KANGJiajia ZHANGRuitao ZHUXiaoli 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

    5. [5]

      Jianjun LIMingjie RENLili ZHANGLingling ZENGHuiling WANGXiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe2O4@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187

    6. [6]

      Hao Wu Zhen Liu Dachang Bai1H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020

    7. [7]

      Liyang ZHANGDongdong YANGNing LIYuanyu YANGQi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

    8. [8]

      Zhaoxin LIRuibo WEIMin ZHANGZefeng WANGJing ZHENGJianbo LIU . Advancements in the construction of inorganic protocells and their cell mimic and bio-catalytical applications. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2286-2302. doi: 10.11862/CJIC.20240235

    9. [9]

      Chi Li Jichao Wan Qiyu Long Hui Lv Ying XiongN-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016

    10. [10]

      Meijin Li Xirong Fu Xue Zheng Yuhan Liu Bao Li . The Marvel of NAD+: Nicotinamide Adenine Dinucleotide. University Chemistry, 2024, 39(9): 35-39. doi: 10.12461/PKU.DXHX202401027

    11. [11]

      Hong Zheng Xin Peng Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058

    12. [12]

      Yuena Yu Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076

    13. [13]

      Xinghai Li Zhisen Wu Lijing Zhang Shengyang Tao . Machine Learning Enables the Prediction of Amide Bond Synthesis Based on Small Datasets. Acta Physico-Chimica Sinica, 2025, 41(2): 100010-. doi: 10.3866/PKU.WHXB202309041

    14. [14]

      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

    15. [15]

      Shuyu Liu Xiaomin Sun Bohan Song Gaofeng Zeng Bingbing Du Chongshen Guo Cong Wang Lei Wang . Design and Fabrication of Phospholipid-Vesicle-based Artificial Cells towards Biomedical Applications. University Chemistry, 2024, 39(11): 182-188. doi: 10.12461/PKU.DXHX202404113

    16. [16]

      Ling Liu Haibin Wang Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080

    17. [17]

      Feng Sha Xinyan Wu Ping Hu Wenqing Zhang Xiaoyang Luan Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082

    18. [18]

      Wanmin Cheng Juan Du Peiwen Liu Yiyun Jiang Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066

    19. [19]

      Liangzhen Hu Li Ni Ziyi Liu Xiaohui Zhang Bo Qin Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001

    20. [20]

      Haitang WANGYanni LINGXiaqing MAYuxin CHENRui ZHANGKeyi WANGYing ZHANGWenmin WANG . Construction, crystal structures, and biological activities of two Ln3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

Metrics
  • PDF Downloads(0)
  • Abstract views(253)
  • HTML views(17)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return