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
-
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.
-
Keywords:
- benzamide,
- HepG2 cells,
- anti-hepatoma activity
-
-
-
[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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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.
-
[1]
-
-
-
[1]
Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min 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]
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng 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]
Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce4ⅢCe6Ⅳ(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]
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
-
[5]
Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu 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]
Hao Wu , Zhen Liu , Dachang Bai . 1H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
-
[7]
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi 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]
Zhaoxin LI , Ruibo WEI , Min ZHANG , Zefeng WANG , Jing ZHENG , Jianbo 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]
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
-
[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]
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]
Yuena Yu , Fang Fang . Microwave-Assisted Synthesis of Safinamide Methanesulfonate. University Chemistry, 2024, 39(11): 210-216. doi: 10.3866/PKU.DXHX202401076
-
[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]
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]
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]
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]
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]
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]
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]
Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two LnⅢ3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(253)
- HTML views(17)