Articles

Synthesis of Quinoline Derivatives Catalyzed by α-Chymotrypsin

  • Liang Meng ,
  • Xie Zongbo ,
  • Ai Feng ,
  • Le Zhanggao
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  • a Jiangxi 2011 Joint Center for the Innovative Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013;
    b Department of Applied Chemistry, East China University of Technology, Nanchang 330013

Received date: 2016-04-24

  Revised date: 2016-06-02

  Online published: 2016-07-07

Supported by

Project supported by the National Natural Science Foundation of China (Nos.21262002,21462001,21465002),the Program for Changjiang Scholars and Innovative Research Team in University (No.IRT13054),the Natural Science Foundation of Jiangxi Province (No.20142BAB203008).

Abstract

The α-chymotrypsin-catalyzed Friedländer condensation reaction between 2-aminoaryl ketone and α-methylene ketone was firstly reported, and a series of quinoline derivatives were obtained in moderate to excellent yields. This method is easy to operate and the reaction condition is mild, which not only expands the application of the promiscuity of protease, but also has positive significance for promoting the development of the green chemistry.

Cite this article

Liang Meng , Xie Zongbo , Ai Feng , Le Zhanggao . Synthesis of Quinoline Derivatives Catalyzed by α-Chymotrypsin[J]. Chinese Journal of Organic Chemistry, 2016 , 36(11) : 2704 -2708 . DOI: 10.6023/cjoc201604051

References

[1] Lam, K.-H.; Lee, K. K.-H.; Gambari, R.; Kok, S. H.-L.; Kok, T.-W.; Chan, A. S.-C.; Bian, Z.-X.; Wong, W.-Y.; Wong, R. S.-M.; Lau, F.-Y. Phytomedicine 2014, 21, 877.
[2] Talamas, F. X.; Abbot, S. C.; Anand, S.; Brameld, K. A.; Carter, D. S.; Chen, J.; Davis, D.; de Vicente, J.; Fung, A. D.; Gong, L. J. Med. Chem. 2013, 57, 1914.
[3] Lam, K.-H.; Gambari, R.; Lee, K. K.-H.; Chen, Y.-X.; Kok, S. H.-L.; Wong, R. S.-M.; Lau, F.-Y.; Cheng, C.-H.; Wong, W.-Y.; Bian, Z.-X. Bioorg. Med. Chem. Lett. 2014, 24, 367.
[4] Vandekerckhove, S.; Tran, H. G.; Desmet, T.; D'hooghe, M. Bioorg. Med. Chem. Lett. 2013, 23, 4641.
[5] Ratheesh, M.; Sindhu, G.; Helen, A. Inflammation Res. 2013, 62, 367.
[6] Chen, J.-J.; Chang, Y.-L.; Teng, C.-M.; Su, C.-C.; Chen, I.-S. Planta Med. 2002, 68, 790.
[7] L, C. Sichuan Chem. Ind. 2004, (7), 28 (in Chinese). (梁诚, 四川化工, 2004, (7), 28.)
[8] Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763.
[9] Kouznetsov, V. V.; Méndez, L. Y. V.; Gómez, C. M. M. Curr. Org. Chem. 2005, 9, 141.
[10] Yadav, J.; Rao, P. P.; Sreenu, D.; Rao, R. S.; Kumar, V. N.; Nagaiah, K.; Prasad, A. Tetrahedron Lett. 2005, 46, 7249.
[11] Sloop, J. C. J. Phys. Org. Chem. 2009, 22, 110.
[12] Yang, D.-Q.; Lü, F.; Guo, W. Chin. J. Org. Chem. 2004, 24, 366 (in Chinese). (杨定乔, 吕芬, 郭维, 有机化学, 2004, 24, 366.)
[13] (a) Fehnel, E. A. J. Org. Chem. 1966, 31, 2899.
(b) Gladiali, S.; Chelucci, G.; Mudadu, M. S.; Gastaut, M.-A.; Thummel, R. P. J. Org. Chem. 2001, 66, 400.
(c) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P.; Sager, J. W.; Volante, R. J. Org. Chem. 2003, 68, 467.
[14] (a) Sliskovic, D.; Picard, J.; Roark, W.; Roth, B.; Ferguson, E.; Krause, B.; Newton, R.; Sekerke, C.; Shaw, M. J. Med. Chem. 1991, 34, 367.
(b) Suzuki, M.; Iwasaki, H.; Fujikawa, Y.; Kitahara, M.; Sakashita, M.; Sakoda, R. Bioorg. Med. Chem. 2001, 9, 2727.
[15] (a) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257.
(b) Arumugam, P.; Karthikeyan, G.; Atchudan, R.; Muralidharan, D.; Perumal, P. T. Chem. Lett. 2005, 34, 314.
[16] Mogilaiah, K.; Reddy, C. S. Synth. Commun. 2003, 33, 3131.
[17] Long, Y.-H.; Liang, L.-H.; Yang, D.-Q. Chin. J. Org. Chem. 2009, 29, 1 (in Chinese). (龙玉华, 梁丽华, 杨定乔, 有机化学, 2009, 29, 1.)
[18] (a) Secundo, F.; Carrea, G. Chem.-Eur. J. 2003, 9, 3194.
(b) Drauz, K. Enzyme Catalysis in Organic Synthesis:A Comprehensive Handbook, John Wiley & Sons, 2012, p. 67.
(c) Reetz, M. T. Curr. Opin. Chem. Biol. 2002, 6, 145.
[19] Monsan, P.; Paul, F. FEMS Microbiol. Rev. 1995, 16, 187.
[20] (a) Du, L.-L.; Wu, Q.; Chen, C.-X.; Liu, B.-K.; Lin, X.-F. J. Mol. Catal. B:Enzym. 2009, 58, 208.
(b) Iwai, N.; Kitahara, Y.; Kitazume, T. J. Mol. Catal. B:Enzym. 2011, 73, 1.
[21] Busto, E.; Gotor-Fernández, V.; Gotor, V. Chem. Soc. Rev. 2010, 39, 4504.
[22] Ge, X.; Lai, Y.-F.; Chen, X.-Z. Chin. J. Org. Chem. 2013, 33, 1686 (in Chinese). (葛新, 赖依峰, 陈新志, 有机化学, 2013, 33, 1686.)
[23] Xie, B.-H.; Guan, Z.; He, Y.-H. Biocatal. Biotransform. 2012, 30, 238.
[24] Wang, J.-L.; Li, X.; Xie, H.-Y.; Liu, B.-K.; Lin, X.-F. J. Bio-technol. 2010, 145, 240.
[25] Kise, H.; Hayakawa, A.; Noritomi, H. J. Biotechnol. 1990, 14, 239.
[26] Enugala, R.; Nuvvula, S.; Kotra, V.; Varala, R.; Adapa, S. R. Heterocycles 2008, 75, 2523.
[27] Wang, H.-S.; Zeng, J.-E. Chin. J. Org. Chem. 2010, 30, 1072 (in Chinese). (王宏社, 曾君娥, 有机化学, 2010, 30, 1072.)

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