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

1.
a School of Pharmaceutical Sciences, Xiamen, Fujian 361102, China;
2.
b Medical College, Xiamen University, Xiamen, Fujian 361102, China

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.
- benzamide,
- HepG2 cells,
- anti-hepatoma activity
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.
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沈阳化工大学材料科学与工程学院沈阳 110142