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]

      Pengli GUANRenhu BAIXiuling SUNBin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058

    2. [2]

      Jichao XUMing HUXichang CHENChunhui WANGLeichen WANGLingyi ZHOUXing HEXiamin CHENGSu JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144

    3. [3]

      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

    4. [4]

      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

    5. [5]

      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

    6. [6]

      Xueqi YangJuntao ZhaoJiawei YeDesen ZhouTingmin DiJun Zhang . 调节NNU-55(Fe)的d带中心以增强CO2吸附和光催化活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100074-0. doi: 10.1016/j.actphy.2025.100074

    7. [7]

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

    8. [8]

      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

    9. [9]

      Xiyuan Zhang Rui Dong Yang Yang Jiapeng Ding Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062

    10. [10]

      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

    11. [11]

      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

    12. [12]

      Yajuan XingHui XueJing SunNiankun GuoTianshan SongJiawen SunYi-Ru HaoQin Wang . Cu3P-Induced Charge-Oriented Transfer and Surface Reconstruction of Ni2P to Achieve Efficient Oxygen Evolution Activity. Acta Physico-Chimica Sinica, 2024, 40(3): 2304046-0. doi: 10.3866/PKU.WHXB202304046

    13. [13]

      Qing XueShengyi LiYanan ZhaoPeng ShengLi XuZhengxi LiBo ZhangHui LiBo WangLibin YangYuliang CaoZhongxue Chen . Novel Alkaline Sodium-Ion Battery Capacitor Based on Active Carbon||Na0.44MnO2 towards Low Cost, High-Rate Capability and Long-Term Lifespan. Acta Physico-Chimica Sinica, 2024, 40(2): 2303041-0. doi: 10.3866/PKU.WHXB202303041

    14. [14]

      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

    15. [15]

      Yu WangHaiyang ShiZihan ChenFeng ChenPing WangXuefei Wang . 具有富电子Ptδ壳层的空心AgPt@Pt核壳催化剂:提升光催化H2O2生成选择性与活性. Acta Physico-Chimica Sinica, 2025, 41(7): 100081-0. doi: 10.1016/j.actphy.2025.100081

    16. [16]

      Lifang HEWenjie TANGYaoze LUOMingsheng LIANGJianxin TANGYuxuan WUFuxing ZHANGXiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012

    17. [17]

      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

    18. [18]

      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

    19. [19]

      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

    20. [20]

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

Metrics
  • PDF Downloads(0)
  • Abstract views(360)
  • HTML views(22)

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