Synthesis of Quinoline Derivatives Catalyzed by α-Chymotrypsin

doi:10.6023/cjoc201604051

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (11): 2704-2708.DOI: 10.6023/cjoc201604051 Previous Articles Next Articles

Articles

α-糜蛋白酶催化合成喹啉衍生物

梁萌^b, 谢宗波^a,b, 艾锋^b, 乐长高^a,b

a 东华理工大学江西省质谱科学与仪器2011协同创新中心南昌 330013;
b 东华理工大学应用化学系南昌 330013

收稿日期:2016-04-24 修回日期:2016-06-02 发布日期:2016-07-07
通讯作者: 谢宗波, 乐长高 E-mail:zhgle@ecit.cn;zbxie@ecit.cn
基金资助:
国家自然科学基金（Nos.21262002，21462001，21465002）、长江学者和创新团队发展计划（No.IRT13054）、江西省自然科学基金（No.20142BAB203008）资助项目.

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

Received:2016-04-24 Revised:2016-06-02 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).

1. Synthesis of Quinoline Derivatives Catalyzed by α-Chymotrypsin.PDF(1989KB)

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.

Key words: α-chymotrypsin, Friedlä, nder condensation, quinoline derivatives, biocatalysis

Cite this article

Liang Meng, Xie Zongbo, Ai Feng, Le Zhanggao. Synthesis of Quinoline Derivatives Catalyzed by α-Chymotrypsin[J]. Chin. J. Org. Chem., 2016, 36(11): 2704-2708.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.)

α-糜蛋白酶催化合成喹啉衍生物

Synthesis of Quinoline Derivatives Catalyzed by α-Chymotrypsin

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Kexin Li, Qingyuan Yang, Pengpeng Zhang, Wuyuan Zhang. Research Progress of Peroxygenase-Catalyzed Reactions Driven by in-situ Generation of H₂O₂ [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 732-741.
[2]	Zhigang Zeng, Xianke Sang, Bo Yuan, Minghu Wu, Wuyuan Zhang. Advances of Haloperoxidases-Catalyzed Green Halogenation Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 959-968.
[3]	Feng Qin, Lin Tang, Fei Huang, Xiaoyue Li, Wu Zhang. Copper-Catalyzed Three-Component Synthesis of Quinolines via Oxidation and Aza-Diels-Alder Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 318-324.
[4]	Jiang Guofang, Lu Yue, Li Hongxia, Hu Zhiyu, Zhu Xiao, Xie Zongbo, Le Zhanggao. New Use of Non-natural Catalytic Activity of Pepsin: Highly Efficient Synthesis of Tetrahydroquinazolines [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2827-2835.
[5]	Peng Mei, Zheng Yangfan, Huang Hao, Ye Jia, Deng Xingguo, He Chunlian. Visible-Light-Induced Cycloaddition Involving N-Propargylanilines with Arylsulfonylhydrazides: Rapid Access to 3-Sulfonated Quinoline Derivatives without Base and Catalyst [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2078-2085.
[6]	Xie Zongbo, Li Hongxia, Liu Liansheng, Lan Jin, Hu Zhiyu, Le Zhanggao. Synthesis of Quinazolinone Derivatives Catalyzed by Alkaline Protease [J]. Chin. J. Org. Chem., 2019, 39(9): 2632-2638.
[7]	Zheng He, Zhou Yuke, Lin Xianfu, Wu Qi. Recent Developments in Protein Engineering and Catalytic Oxidations of Baeyer-Villiger Monooxygenase [J]. Chin. J. Org. Chem., 2019, 39(4): 903-915.
[8]	Ni Guowei, Tang Jiawei, Zou Jie, Chen Shaoxin, Ju Dianwen, Zhang Fuli. Recent Advances on Carbonyl Reductases for Dynamic Kinetic Resolution [J]. Chin. J. Org. Chem., 2019, 39(2): 339-349.
[9]	Yan Yaru, Qi Bowen, Mo Ting, Wang Xiaohui, Wang Juan, Shi Shepo, Liu Xiao, Tu Pengfei. Research Progress of Rhamnosyltransferase [J]. Chin. J. Org. Chem., 2018, 38(9): 2281-2295.
[10]	Yang Jingwen, Chen Jianbo, Wang Shijie, Wu Xiaomei, Ma Baodi, Xu Yi. “One-Pot” Chemo-enzymatic Synthesis of Chiral α-Halogenated Aryl Alcohols [J]. Chin. J. Org. Chem., 2018, 38(7): 1811-1816.
[11]	Deng Dun, Zhang Yun, Sun Aijun, Sai Ke, Hu Yunfeng. Functional Characterization of a New Antarctic Microbial Esterase EST112-2 and Its Use in the Preparation of Chiral Tertiary Alcohol (S)-Linalool [J]. Chin. J. Org. Chem., 2018, 38(5): 1185-1192.
[12]	Wang Bin, Ye Wenbo, Yan Zicong, Wan Changfeng, Hou Haoqing, Wang Zhiyong. A New Catalyst-Free Synthesis of 2,3-Dicarboxylic Ester Quinoline Derivatives [J]. Chin. J. Org. Chem., 2018, 38(2): 504-508.
[13]	Shi Lei, Xu Jingjing, Bi Jingjing, Zhang Zhiguo, Liu Tongxin, Yang Xiaolan, Zhang Guisheng. Synthesis and Biological Activity of Benzo[h]quinolinium Hydrazine Compounds [J]. Chin. J. Org. Chem., 2018, 38(11): 3016-3025.
[14]	Li Zhilin, Zhou Haiyan, Guan Zhi. Synthesis of Anticogulant Warfarin and Its Derivatives by the Crude Earthwarm Extract [J]. Chin. J. Org. Chem., 2017, 37(6): 1494-1500.
[15]	Fu Shaobin, Meng Qingfengb, Xin Qinga, Xiao Shijia. Biocatalytic Synthesis of a Novel Corosolic Acid Derivative [J]. Chin. J. Org. Chem., 2016, 36(11): 2743-2745.