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 shu

Synthesis of Quinoline Derivatives Catalyzed by α-Chymotrypsin

Liang Meng ^b ,
Xie Zongbo ^a,b,*,, ,
Ai Feng ^b ,
Le Zhanggao ^a,b,*,,

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

Corresponding author: Xie Zongbo, zbxie@ecit.cn Le Zhanggao, zhgle@ecit.cn
Received Date: 24 April 2016
Revised Date: 2 June 2016

Fund Project: the National Natural Science Foundation of China 21262002the National Natural Science Foundation of China 21462001the National Natural Science Foundation of China 21465002the Natural Science Foundation of Jiangxi Province 20142BAB203008the Program for Changjiang Scholars and Innovative Research Team in University IRT13054

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.
- α-chymotrypsin,
- Friedländer condensation,
- quinoline derivatives,
- biocatalysis
1. [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. doi: 10.1016/j.phymed.2014.02.005
2. [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. [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. doi: 10.1016/j.bmcl.2013.10.072
4. [4]
  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
5. [5]
  Ratheesh, M.; Sindhu, G.; Helen, A. Inflammation Res. 2013, 62, 367. doi: 10.1007/s00011-013-0588-1
6. [6]
  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
7. [7]
  L, C. Sichuan Chem. Ind. 2004, (7), 28 (in Chinese).
8. [8]
  Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763. doi: 10.1021/ol0476218
9. [9]
  Kouznetsov, V. V.; Méndez, L. Y. V.; Gómez, C. M. M. Curr. Org. Chem. 2005, 9, 141. doi: 10.2174/1385272053369196
10. [10]
  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
11. [11]
  Sloop, J. C. J. Phys. Org. Chem. 2009, 22, 110. doi: 10.1002/poc.v22:2
12. [12]
  Yang, D.-Q.; Lü, F.; Guo, W. Chin. J. Org. Chem. 2004, 24, 366 (in Chinese).
13. [13]
  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. [14]
  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. [15]
  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. [16]
  Mogilaiah, K.; Reddy, C. S. Synth. Commun. 2003, 33, 3131. doi: 10.1081/SCC-120023427
17. [17]
  Long, Y.-H.; Liang, L.-H.; Yang, D.-Q. Chin. J. Org. Chem. 2009, 29, 1 (in Chinese).
18. [18]
  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. [19]
  Monsan, P.; Paul, F. FEMS Microbiol. Rev. 1995, 16, 187. doi: 10.1111/fmr.1995.16.issue-2-3
20. [20]
  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. [21]
  Busto, E.; Gotor-Fernández, V.; Gotor, V. Chem. Soc. Rev. 2010, 39, 4504. doi: 10.1039/c003811c
22. [22]
  Ge, X.; Lai, Y.-F.; Chen, X.-Z. Chin. J. Org. Chem. 2013, 33, 1686 (in Chinese). doi: 10.6023/cjoc201212048
23. [23]
  Xie, B.-H.; Guan, Z.; He, Y.-H. Biocatal. Biotransform. 2012, 30, 238. doi: 10.3109/10242422.2012.662961
24. [24]
  Wang, J.-L.; Li, X.; Xie, H.-Y.; Liu, B.-K.; Lin, X.-F. J. Bio-technol. 2010, 145, 240.
25. [25]
  Kise, H.; Hayakawa, A.; Noritomi, H. J. Biotechnol. 1990, 14, 239. doi: 10.1016/0168-1656(90)90110-W
26. [26]
  Enugala, R.; Nuvvula, S.; Kotra, V.; Varala, R.; Adapa, S. R. Heterocycles 2008, 75, 2523. doi: 10.3987/COM-08-11405
27. [27]
  Wang, H.-S.; Zeng, J.-E. Chin. J. Org. Chem. 2010, 30, 1072 (in Chinese).
1. [1]
  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
2. [2]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
3. [3]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
4. [4]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
5. [5]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
6. [6]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
7. [7]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
8. [8]
  Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010
9. [9]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
10. [10]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
11. [11]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
12. [12]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(12): 0-0.
13. [13]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
14. [14]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
15. [15]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
16. [16]
  Zhibei Qu , Changxin Wang , Lei Li , Jiaze Li , Jun Zhang . Organoid-on-a-Chip for Drug Screening and the Inherent Biochemistry Principles. University Chemistry, 2024, 39(7): 278-286. doi: 10.3866/PKU.DXHX202311039
17. [17]
  Yang Liu , Peng Chen , Lei Liu . Chemistry “101 Plan”: Design and Construction of Chemical Biology Textbook. University Chemistry, 2024, 39(10): 45-51. doi: 10.12461/PKU.DXHX202407085
18. [18]
  Tianyu Feng , Guifang Jia , Peng Zou , Jun Huang , Zhanxia Lü , Zhen Gao , Chu Wang . Construction of the Chemistry Biology Experiment Course in the Chemistry “101 Program”. University Chemistry, 2024, 39(10): 69-77. doi: 10.12461/PKU.DXHX202409002
19. [19]
  Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
20. [20]
  Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(2108)
HTML views(122)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142