Synthesis of Aromatic Amide Derivatives and Their Biological Evaluation against Protein Tyrosine Phosphatase 1B and Scr Homology-2 Domain Containing Protein Tyrosine Phosphatase-2

doi:10.6023/cjoc201603045

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2142-2149.DOI: 10.6023/cjoc201603045 Previous Articles Next Articles

ARTICLE

芳酰胺类衍生物的合成及蛋白酪氨酸磷酸酶1B和含SH2结构域蛋白酪氨酸磷酸酶2抑制活性研究

王文龙^a, 骆欢^a, 高雅^a, 高立信^b, 盛丽^b, 周宇波^b, 李佳^b, 李静雅^b, 冯柏年^a

a 江南大学药学院无锡 214122;
b 中国科学院上海药物研究所国家新药筛选中心新药研究国家重点实验室上海 201203

收稿日期:2016-03-28 修回日期:2016-04-27 发布日期:2016-05-17
通讯作者: 李静雅, 冯柏年 E-mail:fengbainian@jiangnan.edu.cn;jyli@simm.ac.cn
基金资助:
国家自然科学基金（No.21472069）和中国科学院上海药物研究所新药研究国家重点实验室（No.SIMM1302KF-05）资助项目.

Synthesis of Aromatic Amide Derivatives and Their Biological Evaluation against Protein Tyrosine Phosphatase 1B and Scr Homology-2 Domain Containing Protein Tyrosine Phosphatase-2

Wang Wenlong^a, Luo Huan^a, Gao Ya^a, Gao Lixin^b, Sheng Li^b, Zhou Yubo^b, Li Jia^b, Li Jingya^b, Feng Bainian^a

a School of Pharmaceutical Science, Jiangnan University, Wuxi 214122;
b State Key Laboratory of Drug Research, National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received:2016-03-28 Revised:2016-04-27 Published:2016-05-17
Supported by:
Project supported by the National Natural Science Foundation of China (No.21472069) and the State Key Laboratory of Drug Research (No.SIMM1302KF-05).

1. Synthesis of Aromatic Amide Derivatives and Their Biological Evaluation against Protein Tyrosine Phosphatase 1B and Scr Homology-2 Domain Containing Protein Tyrosine Phosphatase-2.PDF(1694KB)

Abstract

To explore the chemical space of protein tyrosine phosphatase 1B (PTP1B) inhibitors by changing bis-aromatic amide moiety into aromatic amide moiety, a series of aromatic amide derivatives were designed, synthesized and their biological activities were evaluated against PTP1B and Scr homology-2 domain containing protein tyrosine phosphatase-2 (SHP2). Among them, compound 3c displayed moderate inhibitory activity with IC₅₀ of (5.13±0.21) μmol/L against PTP1B and showed two times selectivity for other related PTPs. Interestingly, compound 12[IC₅₀=(7.47±1.26) μmol/L] showed moderate inhibitory activity against SHP2 and 2-fold selectivity against PTP1B, T-cell protein tyrosine phosphatase (TCPTP) or Src homology-2 domain containing protein tyrosine phosphatase-1 (SHP1) respectively, and offered a novel scaffold to develop new SHP2 inhibitors.

Key words: PTP1B, SHP2, aromatic amide derivatives, inhibitors

Cite this article

Wang Wenlong, Luo Huan, Gao Ya, Gao Lixin, Sheng Li, Zhou Yubo, Li Jia, Li Jingya, Feng Bainian. Synthesis of Aromatic Amide Derivatives and Their Biological Evaluation against Protein Tyrosine Phosphatase 1B and Scr Homology-2 Domain Containing Protein Tyrosine Phosphatase-2[J]. Chin. J. Org. Chem., 2016, 36(9): 2142-2149.

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[1] Tonks,N.K.FEBS J.2013,280,346.
[2] Hendriks,W.J.;Elson,A.;Harroch,S.;Pulido,R.;Stoker,A.;den Hertog,J.FEBS J.2013,280,708.
[3] Nunes-Xavier,C.E.;Martín-Pérez,J.;Elson,A.;Pulido,R.Biochim.Biophys.Acta,Rev.Cancer 2013,1836,211.
[4] Barr,J.Future Med.Chem.2010,2,1563.
[5] Shi,D.;Li,J.;Jiang,B.;Guo,S.;Su,H.;Wang,T.Bioorg.Med.Chem.Lett.2012,22,2827.
[6] Liu,J.;Jiang,F.;Jin,Y.;Zhang,Y.;Liu,J.;Liu,W.;Fu,L.Eur.J.Med.Chem.2012,57,10.
[7] Xie,J.;Tian,J.;Su,L.;Huang,M.;Zhu,X.;Ye,F.;Wan,Y.Bioorg.Med.Chem.Lett.2011,21,4306.
[8] Qian,S.;Li,H.;Chen,Y.;Zhang,W.;Yang,S.;Wu,Y.J.Nat.Prod.2010,73,1743.
[9] Zhang,Y.;Zhang,W.;Hong,D.;Shi,L.;Shen,Q.;Li,J.-Y.;Li,J.;Hu,L.-H.Bioorg.Med.Chem.2008,16,8697.
[10] Li,H.;Wang,S.-C.;Li,Q.-L.;Song,Y.-W.;Liu,X.-Q.Prog.Modern Biomed.2015,15,1595(in Chinese). (李辉,王曙辰,李庆腊,宋玉文,刘晓谦,现代生物医学进展,2015,15,1595.)
[11] Hu,Z.-Q.;Zhang,C.-M.Transl.Med.J.2013,2,113(in Chi-nese). (胡忠倩,张炽敏,转化医学杂志,2013,2,113.)
[12] Gu,J.;Han,T.;Zhao,N.;Xie,X.-D.;Guo,X.Chin.J.Cancer Biother.2013,20,623(in Chinese). (谷佳,韩涛,赵宁,谢晓冬,郭星,中国肿瘤生物治疗杂志,2013,20,623.)
[13] Butterworth,S.;Overduin,M.;Barr,A.J.Future Med.Chem.2014,6,1423.
[14] Munter,S.D.;Kohn,M.;Bollen,M.ACS Chem.Biol.2013,8,36.
[15] Wang,W.-L.;Huang,C.;Gao,L.-X.;Tang,C.-L.;Wang,J.-Q.;Wu,M.-C.;Sheng,L.;Chen,H.-J.;Nan,F.-J.;Li,J.-Y.;Li,J.;Feng,B.Bioorg.Med.Chem.Lett.2014,24,1889.
[16] Carrilho,R.M.B.;Almeida,A.R.;Kiss,M.;Kollár,L.;Skoda-Földes,R.;D?browski,J.M.;Moreno,M.J.S.M.;Pereira,M.M.Eur.J.Org.Chem.2015,1840.
[17] Konovalova,S.A.;Avdeenko,A.P.;Santalova,A.A.;Pala-marchuk,G.V.;D'yakonenko,V.V.;Shishkin,O.V.Russ.J.Org.Chem.2015,51,42.
[18] Zhang,L.;Xu,W.Y.;Chang,G.J.CN 102604095,2012[Chem.Abstr.2012,157,295637].
[19] Wang,K.L.;Li,X.G.;Liu,F.Y.;Zhang,H.F.;Li,X.Y.;Mao,C.X.;Zhang,J.J.;Wang,R.;Wang,G.J.;Dai,Y.Q.;Wang,K.;Zhang,H.Y.;Gong,Y.L.CN 103539692,2014[Chem.Abstr.2014,160,294897].
[20] Sellarajah,S.;Lekishvili,T.;Bowring,C.;Thompsett,A.R.;Rudyk,H.;Birkett,C.R.;Brown,D.R.;Gilbert,I.H.J.Med.Chem.2004,47,5515.
[21] Kazutoshi,O.;Takeshi,S.WO 2014077324,2014[Chem.Abstr.2014,160,740581].
[22] Miller,R.E.;Reid,W.A.Exp.Parasitol.1986,61,359.
[23] Urbanski,J.;Manek,M.B.Pol.J.Chem.1983,57,603.
[24] Coles,S.J.;Gale,P.A.;Hursthouse,M.B.;Light,M.E.;Warriner,C.N.Supramol.Chem.2004,16,469.
[25] Wang,W.-L.;Yang,D.-L.;Gao,L.-X.;Tang,C.-L.;Ma,W.-P.;Ye,H.-H.;Zhang,S.-Q.;Zhao,Y.-N.;Xu,H.-J.;Hu,Z.;Chen,X.;Fan,W.-H.;Chen,H.-J.;Li,J.-Y.;Nan,F.-J.;Li,J.;Feng.B.Molecules 2013,19,102.
[26] Wang,W.-L.;Chen,X.;Gao,L.-X.;Sheng,L.;Li,J.-Y.;Li,J.;Feng,B.Chem.Biol.Drug Des.2015,86,1161.
[27] Shi,L.;Yu,H.-P.;Zhou,Y.-Y.;Du,J.-Q.;Shen,Q.;Li,J.-Y.;Li,J.Acta.Pharmacol.Sin.2008,29,278.

芳酰胺类衍生物的合成及蛋白酪氨酸磷酸酶1B和含SH2结构域蛋白酪氨酸磷酸酶2抑制活性研究

Synthesis of Aromatic Amide Derivatives and Their Biological Evaluation against Protein Tyrosine Phosphatase 1B and Scr Homology-2 Domain Containing Protein Tyrosine Phosphatase-2

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