Chinese Journal of Organic Chemistry >
A Novel Synthetic Route for Berberine Chloride
Received date: 2015-11-16
Revised date: 2016-01-02
Online published: 2016-02-18
Supported by
Project supported by the Fundamental Research Funds for the Central Universities, Southwest University for Nationalities (No. 2014NZYQN21), and the Research Projects Sichuan Provincial Department of Education (No. 15ZB0487).
Berberine chloride was synthesized starting from pyrocatechol in overall 13.6% yield. The key steps include a Hofmann rearrangement, chloromethylation, nucleophilic substitution, hydrolysis, decarboxylation, and cyclization. All of intermediates were determined by 1H NMR, 13C NMR, MS techniques.
Chen Cheng , Luo Zhuoma , Yang Hongjun , Feng Yuchuan . A Novel Synthetic Route for Berberine Chloride[J]. Chinese Journal of Organic Chemistry, 2016 , 36(6) : 1426 -1430 . DOI: 10.6023/cjoc201511028
[1] (a) Samosorn, S.; Tanwirat, B.; Muhamad, N.; Casadei, G.; Tomkiewicz, D.; Lewis, K.; Suksamrarn, A.; Prammananan, T.; Gornall, K. C.; Beck, J. L.; Bremner, J. B. Bioorg. Med. Chem. 2009, 17, 3866.
(b) Park, K. D.; Lee, J. H.; Kim, S. H.; Kang, T. H.; Moon, J. S.; Kim, S. U. Bioorg. Chem. Lett. 2006, 16, 3913.
(c) Park, K. D.; Cho, S. J.; Moon, J. S.; Kim, S. U. Bioorg. Med. Chem. Lett. 2010, 20, 6554.
[2] North-east Pharmaceutical Factory J. Med. Res. 1976, 7, 40 (in Chinese). (东北制药总厂, 医学研究通讯, 1976, 7, 40.)
[3] Wongbutdee, J. Thai Pharm. Health Sci. J. 2008, 4, 78.
[4] (a) Letasiova, S.; Jantova, S.; Cipak, L.; Muckova, M. Cancer Lett. 2006, 239, 254.
(b) Kuo, H. P.; Chuang, T. C.; Yeh, M. H.; Hsu, S. C.; Way, T. D.; Chen, P. Y.; Wang, S. S.; Chang, Y. H.; Kao, M. C.; Liu, J. Y. J. Agric. Food Chem. 2011, 59, 8216.
(c) Ma, Y.; Ou, T. M.; Tan, J. H.; Hou, J. Q.; Huang, S. L.; Gu, L. Q.; Huang, Z. S. Bioorg. Med. Chem. Lett. 2009, 19, 3414.
[5] Bodiwala, H. S.; Sabde, S.; Mitra, D.; Bhutani, K. K.; Singh, I. P. Eur. J. Med. Chem. 2011, 46, 1045.
[6] Yang, P. Tianjin Pharm. 2011, (3), 69 (in Chinese). (杨萍, 天津药学, 2011, (3), 69.)
[7] Gan, R. Y. Int. J. Mod. Biol. Med. 2012, 1, 48.
[8] Zuo, F.; Nakamura, N.; Akao, T.; Hattori, M. Drug Metab. Dispos. 2006, 34, 2064.
[9] Zhang, P.; Li, X. G.; Zhang, Q. W.; Li, J-M.; Ju, J. M.; Du, N.; Liu, X.; Chen, X. H.; Cheng, F. R.; Yang, L.; Xu, C. Q.; Bilal, M. U.; Wei, Y. W.; Lu, Y. J.; Yang, B. Y. Pharmacol. Exp. Ther. 2014, 349, 417.
[10] (a) Kuo, C. L.; Chi, C. W.; Liu, T. Y. Cancer Lett. 2004, 203, 127.
(b) Gautam, R.; Jachak, S. M. Med. Res. Rev. 2009, 29, 767.
[11] Li, Y. H.; Yang. P.; Kong W. J.; Wang Y. X.; Hu, C. Q.; Zuo, Z. Y.; Wang, Y. M.; Gao, H.; Gao L. M.; Feng Y. C.; Du, N. N.; Liu, Y.; Song, D. Q.; Jiang, J. D. J. Med. Chem. 2009, 52, 492.
[12] (a) Decker Justus Liebigs Ann. Chem. 1913, 395, 295.
(b) Nanning Pharmaceutical Chin. J. Pharm. 1973, (7), 1 (in Chinese). (广西南宁制药厂, 医药工业, 1973, (7), 1.)
(c) Hangzhou First Pharmaceutical Reagent Chamber Chin. J. Pharm. 1974, (8), 6 (in Chinese). (杭州第一制药厂试剂室, 医药工业, 1974, (8), 6.)
(d) North-east Pharmaceutical Factory Chin. J. Pharm. 1975, (4), 12 (in Chinese). (东北制药总厂, 医药工业, 1975, (4), 12.)
(e) Rueffer, M.; Zenk*, M. H. Tetrahedron Lett. 1985, 26, 201.
(f) Ishii, H.; Ozawa, M.; Ohta, S., Harayama, T.; Ishikawa, T. Heterocycles 1994, 37, 897.
(g) Iwasa, K.; Kamigauchi, M.; Ueki, M.; Taniguchi, M. Eur. J. Med. Chem. 1996, 31, 469.
(h) Yang, P.; Song, D. Q.; Li, Y. H.; Kong, W. J.; Wang Y. X.; Gao, L. M.; Liu, S. Y.; Cao, R. Q.; Jiang, J. D. Bioorg. Med. Chem. Lett. 2008, 18, 4675.
(i) Nechepurenko, I. V.; Komarova, N. I.; Vasil' ev, V. G.; Salakhutdinov, N. F. Chem. Nat. Compd. 2013, 48, 1047.
(j) Gatland, A. E.; Pilgrim, B. S.; Procopiou, P. A.; Donohoe, T. J. Angew. Chem., Int. Ed. 2014, 53, 14555.
(k) Reddy, V.; Jadhav, A. S.; Anand, R. V. Org. Biomol. Chem. 2015, 13, 3732.
[13] Spaeth; Schmidt Monatsh. Chem. 1929, 53~54, 469.
[14] Sugasawa; Shigehara Yakugaku Zasshi 1942, 62, 532.
[15] Sun, Y. Y.; Yi, J.; Lu, X.; Zhang, Z. Q.; Xiao, B.; Fu, Y. Chem. Commun. 2014, 50, 11060.
[16] Itoh; Chika; Takagi; Nishiyama J. Org. Chem. 1993, 58, 5717.
[17] Boehm Arch. Pharm. 1929, 708, 714.
[18] Jia, Y. L.; Zhou, P. F.; Wang, Y.; Dong, X. Y.; Liu, X. H.; Pan, L. L.; Xin, H.; Zhu, Y. Z. Eur. J. Med. Chem. 2012, 55, 176.
[19] Sebeetal J. Chin. Chem. Soc. 1967, 14, 91.
[20] Tanabe, G.; Sugano, Y.; Shirato; Miki; Sonoda, N.; Tsutsui, N.; Morikawa, T.; Ninomiya, K.; Yoshikawa, M.; Muraoka, O. Nat. Prod. 2015, 78, 1536.
[21] Pan, J. F.; Yu, C.; Zhu, D. Y.; Zhang, H.; Ren, J. Y. CN 1314347, 2001 [Chem. Abstr. 2002, 137, 370266].
[22] Meskheli; Vachnadze; Bakuridze Chem. Nat. Compd. 2011, 47, 154.
/
〈 |
|
〉 |