Synthesis of Quinoline Derivatives Catalyzed by α-Chymotrypsin
- Corresponding author: Xie Zongbo, zbxie@ecit.cn Le Zhanggao, zhgle@ecit.cn
Citation:
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
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.
doi: 10.1016/j.phymed.2014.02.005
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.
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.
doi: 10.1016/j.bmcl.2013.10.072
Vandekerckhove, S.; Tran, H. G.; Desmet, T.; D'hooghe, M. Bioorg. Med. Chem. Lett. 2013, 23, 4641.
doi: 10.1016/j.bmcl.2013.06.014
Ratheesh, M.; Sindhu, G.; Helen, A. Inflammation Res. 2013, 62, 367.
doi: 10.1007/s00011-013-0588-1
Chen, J.-J.; Chang, Y.-L.; Teng, C.-M.; Su, C.-C.; Chen, I.-S. Planta Med. 2002, 68, 790.
doi: 10.1055/s-2002-34412
L, C. Sichuan Chem. Ind. 2004, (7), 28 (in Chinese).
Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763.
doi: 10.1021/ol0476218
Kouznetsov, V. V.; Méndez, L. Y. V.; Gómez, C. M. M. Curr. Org. Chem. 2005, 9, 141.
doi: 10.2174/1385272053369196
Yadav, J.; Rao, P. P.; Sreenu, D.; Rao, R. S.; Kumar, V. N.; Nagaiah, K.; Prasad, A. Tetrahedron Lett. 2005, 46, 7249.
doi: 10.1016/j.tetlet.2005.08.042
Sloop, J. C. J. Phys. Org. Chem. 2009, 22, 110.
doi: 10.1002/poc.v22:2
Yang, D.-Q.; Lü, F.; Guo, W. Chin. J. Org. Chem. 2004, 24, 366 (in Chinese).
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.
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.
MCNAUGHTON, B. R.; MILLER, B. L. ORG. LETT. 2003, 5, 4257.
Mogilaiah, K.; Reddy, C. S. Synth. Commun. 2003, 33, 3131.
doi: 10.1081/SCC-120023427
Long, Y.-H.; Liang, L.-H.; Yang, D.-Q. Chin. J. Org. Chem. 2009, 29, 1 (in Chinese).
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.
Monsan, P.; Paul, F. FEMS Microbiol. Rev. 1995, 16, 187.
doi: 10.1111/fmr.1995.16.issue-2-3
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.
Busto, E.; Gotor-Fernández, V.; Gotor, V. Chem. Soc. Rev. 2010, 39, 4504.
doi: 10.1039/c003811c
Ge, X.; Lai, Y.-F.; Chen, X.-Z. Chin. J. Org. Chem. 2013, 33, 1686 (in Chinese).
doi: 10.6023/cjoc201212048
Xie, B.-H.; Guan, Z.; He, Y.-H. Biocatal. Biotransform. 2012, 30, 238.
doi: 10.3109/10242422.2012.662961
Wang, J.-L.; Li, X.; Xie, H.-Y.; Liu, B.-K.; Lin, X.-F. J. Bio-technol. 2010, 145, 240.
Kise, H.; Hayakawa, A.; Noritomi, H. J. Biotechnol. 1990, 14, 239.
doi: 10.1016/0168-1656(90)90110-W
Enugala, R.; Nuvvula, S.; Kotra, V.; Varala, R.; Adapa, S. R. Heterocycles 2008, 75, 2523.
doi: 10.3987/COM-08-11405
Wang, H.-S.; Zeng, J.-E. Chin. J. Org. Chem. 2010, 30, 1072 (in Chinese).
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