Synthesis and Protein Tyrosine Phosphatase 1B Inhibitory Activity of Novel Chalcone Derivatives Containing 3,4-Dihydroquinolin-2(1H)-one Moiety

doi:10.6023/cjoc201206018

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2108-2114.DOI: 10.6023/cjoc201206018 Previous Articles Next Articles

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含3,4-二氢-2(1H)-喹啉酮结构查尔酮衍生物的合成及蛋白酪氨酸磷酸酯酶1B抑制活性研究

孙良鹏^a, 姜哲^b, 高立信^c, 李英哲^a, 孙立云^a, 李佳^c, 朴虎日^a

a 长白山生物资源与功能分子教育部重点实验室延边大学药学院延吉 133002;
b 延边大学附属医院延吉 133002;
c 国家新药筛选中心中国科学院上海药物研究所上海 201203

收稿日期:2012-06-18 修回日期:2012-07-16 发布日期:2012-07-19
通讯作者: 李佳, 朴虎日 E-mail:piaohuri@ybu.edu.cn; jli@mail.shcnc.ac.cn
基金资助:
国家自然科学基金(Nos. 20962021, 81125023)资助项目.

Synthesis and Protein Tyrosine Phosphatase 1B Inhibitory Activity of Novel Chalcone Derivatives Containing 3,4-Dihydroquinolin-2(1H)-one Moiety

Sun Liangpeng^a, Jiang Zhe^b, Gao Lixin^c, Li Yingzhe^a, Sun Liyun^a, Li Jia^c, Piao Huri^a

a Key Laboratory of Natural Resources of Changbai Mountain & Functional Molecules, Ministry of Education, College of Pharmacy, Yanbian University, Yanji 133002;
b Yanbian University Hospital, Yanji 133002;
c National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received:2012-06-18 Revised:2012-07-16 Published:2012-07-19
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20962021, 81125023).

Protein tyrosine phosphatase 1B (PTP1B) has recently been identified as new drug target for type II diabetes and obesity due to it is a negative regulator of the insulin and leptin-signaling pathway. In order to find new nonphosphonate-based pTyr mimetics, a series of novel chalcone derivatives bearing the 3,4-dihydroquinolin-2(1H)-one moieties (4a～4n) were designed, synthesized, and evaluated for their PTP1B inhibitory activity. The results demonstrated that all compounds presented potent inhibitory activities against PTP1B, among which compounds 4e and 4i exhibited most potent with IC₅₀ value of (4.64±0.38) and (4.36±0.41) μmol/L, respectively.

Key words: chalcone, 3,4-dihydroquinolin-2(1H)-one, PTP1B inhibitor

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Sun Liangpeng, Jiang Zhe, Gao Lixin, Li Yingzhe, Sun Liyun, Li Jia, Piao Huri. Synthesis and Protein Tyrosine Phosphatase 1B Inhibitory Activity of Novel Chalcone Derivatives Containing 3,4-Dihydroquinolin-2(1H)-one Moiety[J]. Chin. J. Org. Chem., 2012, 32(11): 2108-2114.

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[1] (a) Neel, B. G.; Tonks, N. K. Curr. Opin. Cell Biol. 1997, 9, 193.

(b) Hunter, T. Cell 2000, 100, 113.

(c) Tonks, N. K.; Neel, B.G. Curr. Opin. Cell Biol. 2001, 13, 182.

[2] (a) Elchebly, M.; Payette, P.; Michaliszyn, E.; Cromlish, W.; Collins, S.; Loy, A. L.; Normandin, D.; Cheng, A.; Himms-Hagen, J.; Chan C. C.; Ramachandran, C.; Gresser, M. J.; Tremblay, M. L.; Kennedy, B. P. Science 1999, 283, 1544.

(b) Klaman, L. D.; Boss, O.; Peroni, O. D.; Kim, J. K.; Martino, J. L.; Zabolotny, J. M.; Moghal, N.; Lubkin, M.; Kim, Y. B.; Sharpe, A. H.; Stricker-Krongrad, A.; Shulman, G. I.; Neel, B. G.; Kahn, B. B. Mol. Cell Biol. 2000, 20, 5479.

[3] Zinker, B. A.; Rondinone, C. M.; Trevillyan, J. M.; Gum, R. J.; Clampit, J. E.; Waring, J. F.; Xie, N.; Wilcox, D.; Jacobson, P.; Frost, L.; Kroeger, P. E.; Reilly, R. M.; Koterski, S.; Opgenorth, T. J.; Ulrich, R. G.; Crosby, S.; Butler, M.; Murray, S. F.; McKay, R. A.; Bhanot, S.; Monica, B. P.; Jirousek, M. R. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 11357.

[4] Rondinone, C. M.; Trevillyan, J. M.; Clampit, J. E.; Gum, R. J.; Berg, C.; Kroeger, P.; Frost, L.; Zinker, B. A.; Reilly, R.; Ulrich, R.; Butler, M.; Monia, B. P.; Jirousek, M. R.; Waring, J. F. Diabetes 2002, 51, 2405.

[5] Ramachandran, C.; Kennedy, B. P. Curr. Top Med. Chem. 2003, 3, 749.

[6] Combs, A. P. J. Med. Chem. 2010, 53, 2333.

[7] Vogel, S.; Ohmayer, S.; Brunner, G.; Heilmann, J. Bioorg. Med. Chem. 2008, 16, 4286.

[8] (a) Chen, Z. H.; Zheng, C. J.; Sun, L. P.; Piao, H. R. Eur. J. Med. Chem. 2010, 45, 5739.

(b) Liu, X. F.; Zheng, C. J.; Sun, L. P.; Liu, X. K.; Piao, H. R. Eur. J. Med. Chem. 2011, 46, 3469.

[9] Chiaradia, L. D.; dos Santos, R.; Vitor, C. E.; Vieira, A. A.; Leal, P. C.; Nunes, R. J.; Calixto, J. B.; Yunes, R. A. Bioorg. Med. Chem. 2008, 16, 658.

[10] Vogel, S.; Heilmann, J. J. Nat. Prod. 2008, 71, 1237.

[11] Domínguez, J. N.; León, C.; Rodrigues, J.; Gamboa de Domínguez, N.; Gut, J.; Rosenthal, P. J. J. Med. Chem. 2005, 48,3654.

[12] Daskiewicz, J. B.; Depeint, F.; Viornery, L.; Bayet, C.; Comte-Sarrazin, G.; Comte, G.; Gee, J. M.; Johnson, I. T.; Ndjoko, K.; Hostettmann, K.; Barron, D. J. Med. Chem. 2005, 48, 2790.

[13] Sui, X.; Quan, Y. C.; Chang, Y.; Zhang, R. P.; Xu, Y. F.; Guan, L. P. Med. Chem. Res. 2011, 20, 1.

[14] Chen, R. M.; Hu, L. H.; An, T. Y.; Li, J.; Shen, Q. Bioorg. Med. Chem. Lett. 2002, 12, 3387.

[15] Yoon, G.; Lee, W.; Kim, S. N.; Cheon, S. H. Bioorg. Med. Chem. Lett. 2009, 19, 5155.

[16] Liu, Z.; Lee, W.; Kim, S. N.; Yoon, G.; Cheon, S. H. Bioorg. Med. Chem. Lett. 2011, 21, 3755.

[17] Ge, H. X.; Wang, L. C. Prog. Pharm. Sci. 2005, 29, 310 (in Chinese).

(葛海霞, 王礼琛, 药学学报, 2005, 29, 310.)

[18] Patil, V.; Tilekar, K.; Mehendale-Munj, S.; Mohan, R.; Ramaa, C. S. Eur. J. Med. Chem. 2010, 49, 4539.

[19] Meng, F. L.; Zheng, C. J.; Li, Y. J.; Sun, L. P.; Liu, X. K.; Zhang, T. Y.; Piao, H. R. Chin. J. Org. Chem. 2012, 32, 183 (in Chinese).

(孟凡领, 郑昌吉, 李因晶, 孙良鹏, 刘学坤, 张天一, 朴虎日, 有机化学, 2012, 32, 183.)

[20] (a) Shi, L.; Yu, H. P.; Zhou, Y. Y.; Du, J. Q.; Shen, Q.; Li, J. Y.; Li, J. Acta Pharmacol. Sin. 2008, 29, 278.

(b) Zhang, W.; Hong, D.; Zhou, Y. Y.; Zhang, Y. N.; Shen, Q.; Li, J. Y.; Hu, L. H.; Li, J. Biochim. Biophys. Acta 2006, 1760, 1505.

含3,4-二氢-2(1H)-喹啉酮结构查尔酮衍生物的合成及蛋白酪氨酸磷酸酯酶1B抑制活性研究

Synthesis and Protein Tyrosine Phosphatase 1B Inhibitory Activity of Novel Chalcone Derivatives Containing 3,4-Dihydroquinolin-2(1H)-one Moiety

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