四丁基溴化铵介导的N-甲基苯胺和色氨酸衍生物的环化芳香化合成β-咔啉

doi:10.6023/cjoc201903077

有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2323-2327.DOI: 10.6023/cjoc201903077 上一篇下一篇

所属专题：陈茹玉先生诞辰100周年

研究简报

四丁基溴化铵介导的N-甲基苯胺和色氨酸衍生物的环化芳香化合成β-咔啉

王震^a, 张玲^b, 张富赓^b, 王彬^a

a 南开大学药学院天津 300353;
b 南开大学附属环湖医院天津 300350

收稿日期:2019-03-30 修回日期:2019-05-16 发布日期:2019-06-03
通讯作者: 张富赓, 王彬 E-mail:clare2006@163.com;wangbin@nankai.edu.cn
基金资助:
国家自然科学基金（No.21172120，21472093）资助项目.

Synthesis of β-Carbolines through Tetra-n-butylammonium Bromide-Mediated Cycloaromatization Reaction of N-Methylaniline with Tryptophan Derivatives

Wang Zhen^a, Zhang Ling^b, Zhang Fugeng^b, Wang Bin^a

a College of Pharmacy, Nankai University, Tianjin 300353;
b Department of Pharmacy, Affiliated Huanhu Hospital of Nankai University, Tianjin 300350

Received:2019-03-30 Revised:2019-05-16 Published:2019-06-03
Contact: 10.6023/cjoc201903077 E-mail:clare2006@163.com;wangbin@nankai.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China ((Nos. 21172120, 21472093).

文章分享

1. 四丁基溴化铵介导的N-甲基苯胺和色氨酸衍生物的环化芳香化合成β-咔啉.PDF(5281KB)

摘要/Abstract

描述了一种四丁基溴化铵介导的环化芳香化反应用于β-咔啉的合成，反应物使用容易得到的色氨酸和N-甲基苯胺.这种不使用金属催化剂的策略是现存β-咔啉合成方法的有益补充.

关键词: β-咔啉, 四丁基溴化铵, N-甲基苯胺, 环化芳香化反应

A mild and efficient ⁿBu₄NBr-mediated oxidative cycloaromatization to prepare β-carbolines from readily available tryptophans and N-methylaniline is described. The present metal free protocol is complementary to the existing methods for the synthesis of aromatic β-carbolines.

Key words: β-carboline, tetra-n-butylammonium bromide, N-methylaniline, cycloaromatization

引用此文

王震, 张玲, 张富赓, 王彬. 四丁基溴化铵介导的N-甲基苯胺和色氨酸衍生物的环化芳香化合成β-咔啉[J]. 有机化学, 2019, 39(8): 2323-2327.

Wang Zhen, Zhang Ling, Zhang Fugeng, Wang Bin. Synthesis of β-Carbolines through Tetra-n-butylammonium Bromide-Mediated Cycloaromatization Reaction of N-Methylaniline with Tryptophan Derivatives[J]. Chin. J. Org. Chem., 2019, 39(8): 2323-2327.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] (a) Cao, R. H.; Peng, W. L.; Wang, Z. H.; Xu, A. L. Curr. Med. Chem. 2007, 14, 479.
(b) Lancianesi, S.; Palmieri, A.; Petrini, M. Chem. Rev. 2014, 114, 7108.
(c) Nagle, A. S.; Khare, S.; Kumar, A. B.; Supek, F.; Buchynskyy, A.; Mathison, C. J. N.; Chennamaneni, N. K.; Pendem, N.; Buckner, F. S.; Gelb, M. H.; Molteni, V. Chem. Rev. 2014, 114, 11305.
(d) Gema, D.; Javier, P. C. Eur. J. Org. Chem. 2011, 2011, 7243.
(e) Zhang, G.-J.; Hu, F.; Jiang, H.; Dai, L.-M.; Liao, H.-B.; Li, N.; Wang, H.-S.; Pan, Y.-M.; Liang, D. Phytochemistry 2018, 145, 68.
(f) Venkataramana, R. P. O.; Hridhay, M.; Nikhil, K.; Khan, S.; Jha, P. N.; Shah, K.; Kumar, D. Bioorg. Med. Chem. Lett. 2018, 28, 1278.
(g) Devi, N.; Kumar, S.; Pandey, S. K.; Singh, V. Asian J. Org. Chem. 2018, 7, 6.
[2] (a) Shilabin, A. G.; Kasanah, N.; Tekwani, B. L.; Hamann, M. T. J. Nat. Prod. 2008, 71, 1218.
(b) Winkler, J. D.; Londregan, A. T.; Hamann, M. T. Org. Lett. 2006, 8, 2591.
[3] (a) Boursereau, Y.; Coldham, I. Bioorg. Med. Chem. Lett. 2004, 14, 5841.
(b) Guan, H.; Chen, H.; Peng, W.; Ma, Y.; Cao, R.; Liu, X.; Xu, A. Eur. J. Med. Chem. 2006, 41, 1167.
(c) Rashid, M. A.; Gustafson, K. R.; Boyd, M. R. J. Nat. Prod. 2001, 64, 1454.
(d) Prinsep, M. R.; Blunt, J. W.; Munro, M. H. G. J. Nat. Prod. 1991, 54, 1068.
(e) Yang, J.-M.; Zhu, Y.-H.; Chen, S.; Lu, X.; Wu, Y.-M.; Ma, F.-E.; Li, L.-P.; Yang, Y.; Shi, Z.-H.; Huang, K.-Y.; Hong, X.; Jiang, P.; Peng, Y. MedChemComm 2018, 9, 100.
(f) Dighe, S. U.; Khan, S.; Soni, I.; Jain, P.; Shukla, S.; Yadav, R.; Sen, P.; Meeran, S. M.; Batra, S. J. Med. Chem. 2015, 58, 3485.
(g) Kamal, A.; Srinivasulu, V.; Nayak, V. L.; Sathish, M.; Shankaraiah, N.; Bagul, C.; Reddy, N. V. S.; Rangaraj, N.; Nagesh, N. ChemMedChem 2014, 9, 2084.
[4] (a) Tang, J.; Wang, Y.; Wang, R.; Dong, Z.; Yang, L.; Zheng, Y.; Liu, J. Chem. Biodiversity 2008, 5, 447.
(b) Wang, Y.-H.; Tang, J.-G.; Wang, R.-R.; Yang, L.-M.; Dong, Z.-J.; Du, L.; Shen, X.; Liu, J.-K.; Zheng, Y.-T. Biochem. Biophys. Res. Commun. 2007, 355, 1091.
(c) Yu, X.; Lin, W.; Li, J.; Yang, M. Bioorg. Med. Chem. Lett. 2004, 14, 3127.
[5] (a) Hagen, T. J.; Skolnick, P.; Cook, J. M. J. Med. Chem. 1987, 30, 750.
(b) Müller, W. E.; Fehske, K. J.; Borbe, H. O.; Wollert, U.; Nanz, C.; Rommelspacher, H. Pharmacol., Biochem. Behav. 1981, 14, 693.
[6] (a) Im, Y.; Lee, J. Y. Chem. Commun. 2013, 49, 5948.
(b) Paul, B. K.; Ghosh, N.; Mukherjee, S. RSC Adv. 2016, 6, 9984.
(c) Swami, S.; Behera, D.; Agarwala, A.; Verma, V. P.; Shrivastava, R. New J. Chem. 2018, Ahead of Print.
[7] (a) Whaley, W. M.; Govindachari, T. R. In Organic Reactions, John Wiley & Sons, Inc., 2004.
(b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
(c) Rao, R. N.; Maiti, B.; Chanda, K. ACS Comb. Sci. 2017, 19, 199.
(d) Gobe, V.; Gandon, V.; Guinchard, X. Adv. Synth. Catal. 2018, 360, 1280.
(e) Glenn, C. C.; Jan, B. Eur. J. Org. Chem. 2004, 2004, 1286.
[8] Bischler, A.; Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26, 1903.
[9] (a) Singh, D.; Sharma, P.; Kumar, R.; Pandey, S. K.; Malakar, C. C.; Singh, V. Asian J. Org. Chem. 2018, 7, 383.
(b) Singh, D.; Hazra, C. K.; Malakar, C. C.; Pandey, S. K.; Kaith, B. S.; Singh, V. ChemistrySelect 2018, 3, 4859.
(c) Kovvuri, J.; Nagaraju, B.; Nayak, V. L.; Akunuri, R.; Rao, M. P. N.; Ajitha, A.; Nagesh, N.; Kamal, A. Eur. J. Med. Chem. 2018, 143, 1563.
(d) Singh, D.; Kumar, V.; Devi, N.; Malakar, C. C.; Shankar, R.; Singh, V. Adv. Synth. Catal. 2017, 359, 1213.
(e) Manasa, K. L.; Tangella, Y.; Ramu, G.; Babu, B. N. ChemistrySelect 2017, 2, 9162.
(f) Galvis, C. E. P.; Kouznetsov, V. V. Synthesis 2017, 49, 4535.
(g) Hati, S.; Sen, S. Tetrahedron Lett. 2016, 57, 1040.
(h) Meesala, R.; Arshad, A. S. M.; Mordi, M. N.; Mansor, S. M. Tetrahedron 2016, 72, 8537.
(i) Kamal, A.; Tangella, Y.; Manasa, K. L.; Sathish, M.; Srinivasulu, V.; Chetna, J.; Alarifi, A. Org. Biomol. Chem. 2015, 13, 8652.
(j) Kamal, A.; Sathish, M.; Prasanthi, A. V. G.; Chetna, J.; Tangella, Y.; Srinivasulu, V.; Shankaraiah, N.; Alarifi, A. RSC Adv. 2015, 5, 90121.
(k) Kamal, A.; Narasimha Rao, M. P.; Swapna, P.; Srinivasulu, V.; Bagul, C.; Shaik, A. B.; Mullagiri, K.; Kovvuri, J.; Reddy, V. S.; Vidyasagar, K.; Nagesh, N. Org. Biomol. Chem. 2014, 12, 2370.
[10] (a) Ding, S.; Shi, Z.; Jiao, N. Org. Lett. 2010, 12, 1540.
(b) Tang, S.; Wang, J.; Xiong, Z.; Xie, Z.; Li, D.; Huang, J.; Zhu, Q. Org. Lett. 2017, 19, 5577.
(c) Mulcahy, S. P.; Varelas, J. G. Tetrahedron Lett. 2013, 54, 6599.
(d) Dhara, S.; Singha, R.; Ahmed, A.; Mandal, H.; Ghosh, M.; Nuree, Y.; Ray, J. K. RSC Adv. 2014, 4, 45163.
(e) Yan, Q.; Gin, E.; Banwell, M. G.; Willis, A. C.; Carr, P. D. J. Org. Chem. 2017, 82, 4328.
(f) Dhiman, S.; Mishra, U. K.; Ramasastry, S. S. V. Angew. Chem., Int. Ed. 2016, 55, 7737.
(g) Pan, X.; Bannister, T. D. Org. Lett. 2014, 16, 6124.
(h) Wang, T.-T.; Zhang, D.; Liao, W.-W. Chem. Commun. 2018, 54, 2048.
[11] Dalvi, B. A.; Lokhande, P. D. Tetrahedron Lett. 2018, 59, 2145.
[12] Nissen, F.; Richard, V.; Alayrac, C.; Witulski, B. Chem. Commun. 2011, 47, 6656.
[13] (a) Varelas, J. G.; Khanal, S.; O'Donnell, M. A.; Mulcahy, S. P. Org. Lett. 2015, 17, 5512.
(b) Webb, N. J.; Marsden, S. P.; Raw, S. A. Org. Lett. 2014, 16, 4718.
[14] (a) Verniest, G.; England, D.; De Kimpe, N.; Padwa, A. Tetrahedron 2010, 66, 1496.
(b) Subba Reddy, B. V.; Rajashekhar Reddy, M.; Yarlagadda, S.; Ravikumar Reddy, C.; Ravi Kumar, G.; Yadav, J. S.; Sridhar, B. J. Org. Chem. 2015, 80, 8807.
[15] Too, P. C.; Chua, S. H.; Wong, S. H.; Chiba, S. J. Org. Chem. 2011, 76, 6159.
[16] Zhu, Y.; Liu, M.; Cai, Q.; Jia, F.; Wu, A. Chem.-Eur. J. 2013, 19, 10132.
[17] (a) Li, L. T.; Huang, J.; Li, H. Y.; Wen, L. J.; Wang, P.; Wang, B. Chem. Commun. 2012, 48, 5187.
(b) Li, L. T.; Li, H. Y.; Xing, L. J.; Wen, L. J.; Wang, P.; Wang, B. Org. Biomol. Chem. 2012, 10, 9519.
[18] Wang, B.; Wong, H. N. C. Bull. Chem. Soc. Jpn. 2018, 91, 710.
[19] Guo, F.; Wang, L.; Mao, S.; Zhang, C.; Yu, J.; Han, J. Tetrahedron 2012, 68, 8367.
[20] (a) Benson, S. C.; Lee, L.; Yang, L.; Snyder, J. K. Tetrahedron 2000, 56, 1165.
(b) Chiotellis, A.; Muller, A.; Mu, L.; Keller, C.; Schibli, R.; Krämer, S. D.; Ametamey, S. M. Mol. Pharmaceutics 2014, 11, 3839.
[21] (a) Garcia, J. M.; Curzon, S. S.; Watts, K. R.; Konopelski, J. P. Org. Lett. 2012, 14, 2054.
(b) Dua, R. K.; Phillips, R. S. Tetrahedron Lett. 1992, 33, 29.
(c) Tang, J.-G.; Wang, Y.-H.; Wang, R.-R.; Dong, Z.-J.; Yang, L.-M.; Zheng, Y.-T.; Liu, J.-K. Chem. Biodiversity 2008, 5, 447.
(d) De Croos, P. Z.; Sangdee, P.; Stockwell, B. L.; Kar, L.; Thompson, E. B.; Johnson, M. E.; Currie, B. L. J. Med. Chem. 1990, 33, 3138.
[22] Xu, W.; Zhao, M.; Wang, Y.; Zhu, H.; Wang, Y.; Zhao, S.; Wu, J.; Peng, S. MedChemComm 2016, 7, 1730.
[23] Sun, R.; Liu, R.; Zhou, C.; Ren, Z.; Guo, L.; Ma, Q.; Fan, W.; Qiu, L.; Yu, H.; Shao, G.; Cao, R. MedChemComm 2015, 6, 2170.
[24] Ikeda, R.; Kimura, T.; Tsutsumi, T.; Tamura, S.; Sakai, N.; Konakahara, T. Bioorg. Med. Chem. Lett. 2012, 22, 3506.
[25] Primas, N.; El-Kashef, H.; Lancelot, J.-C.; Lesnard, A.; Dodd, R. H.; Raulta, S. ARKIVOC 2010, 2010, 14.
[26] Cao, R.; Chen, Q.; Hou, X.; Chen, H.; Guan, H.; Ma, Y.; Peng, W.; Xu, A. Bioorg. Med. Chem. 2004, 12, 4613.

四丁基溴化铵介导的N-甲基苯胺和色氨酸衍生物的环化芳香化合成β-咔啉

Synthesis of β-Carbolines through Tetra-n-butylammonium Bromide-Mediated Cycloaromatization Reaction of N-Methylaniline with Tryptophan Derivatives

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 4

编辑推荐

相关统计

本文评价

[1]	霍新玉, 李文斌, 张博雅, 陈晓飞, 周月婷, 张洁, 韩小强, 代斌. 含苯并咪(噻)唑环的β-咔啉衍生物的合成与杀菌活性[J]. 有机化学, 2018, 38(12): 3356-3362.
[2]	郭亮, 谢建伟, 范文玺, 陈伟, 代斌, 马芹. 双-(1-杂环-β-咔啉)-3-烷氨基衍生物的合成与抗肿瘤活性[J]. 有机化学, 2017, 37(7): 1741-1747.
[3]	郭亮, 范文玺, 陈雪梅, 马芹, 曹日晖. β-咔啉衍生物的合成和初步抗肿瘤活性研究[J]. 有机化学, 2013, 33(02): 332-338.
[4]	赵瑾,宋金勇,王超杰. 4－N－茄呢基氨基苯甲酸糖酯的合成[J]. 有机化学, 2003, 23(7): 714-716.