Efficient Synthesis of Wogonin

doi:10.6023/cjoc202001033

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (6): 1725-1730.DOI: 10.6023/cjoc202001033 Previous Articles Next Articles

汉黄芩素的方便合成

董玮^a, 王欣^a, 葛泽梅^a, 和芳^b, 李润涛^a

a 北京大学药学院天然药物及仿生药物国家重点实验室北京 100191;
b 北京创立科创医药技术开发有限公司北京 100029

收稿日期:2020-01-29 修回日期:2020-03-17 发布日期:2020-04-10
通讯作者: 李润涛 E-mail:lirt@bjmu.edu.cn
基金资助:
国家自然科学基金（No.81673287）资助项目.

Efficient Synthesis of Wogonin

Dong Wei^a, Wang Xin^a, Ge Zemei^a, He Fang^b, Li Runtao^a

a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191;
b Beijing Supertrack Pharma-Tech Co., LTD, Beijing 100029

Received:2020-01-29 Revised:2020-03-17 Published:2020-04-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 81673287).

1. 201725S.pdf(644KB)

Abstract

Wogonin is an important flavonoid with a wide range of pharmacological activities, and its research has received increasing attention. The large amount of wogonin is the basis of in-depth research on it, but currently there are problems, such as difficulty in extracting from natural products, difficult to obtain fully synthetic raw materials, harsh reaction conditions, use of valuable and toxic reagents, difficulty in isolation and purification, or low yields. Herein, an efficient synthesis of wogonin from benzene-1,3,5-triol as starting material via seven steps with total yield of 58% was reported. This method possesses advantages including available starting materials, mild reaction conditions, simple operation and no column chromatography purification, which will provide a foundation for the large-scale preparation and in-depth study of wogonin.

Key words: wogonin, benzene-1,3,5-triol, chrysin, total synthesis

Cite this article

Dong Wei, Wang Xin, Ge Zemei, He Fang, Li Runtao. Efficient Synthesis of Wogonin[J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1725-1730.

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[1] Wang, Y. Z.; Zhang, L.; Zhang, Y. C. Western J. Tradit. Chin. Med. 2018, 31, 138(in Chinese). (王哲元, 张璐, 张有成, 西部中医药, 2018, 31, 138.)
[2] Ren, X. D.; Fu, W.; Zhang, X. Y.; Hu, P.; Wang, Z.; Li, Z. Y. J. New Drugs 2011, 20, 777(in Chinese). (任晓东, 符伟, 张晓芸, 胡珀, 汪嵘, 李志裕, 中国新药杂志, 2011, 20, 777.)
[3] (a) Cho, J.; Lee, H. K. Eur. J. Pharmacol. 2004, 485, 105.
(b) Pang, Y. Y.; Qin, X. M.; Du, G. H. Zhou, Y. Z. Chin. Tradit. Herb. Drugs 2019, 50, 3207(in Chinese). (庞溢媛, 秦雪梅, 杜冠华, 周玉枝, 中草药, 2019, 50, 3207.)
[4] (a) Wu, Y.; Jin, Y. Z.; Zhang, S.; Yan, Y. J.; Zhang, J.; Hao, J. Chin. J. Exp. Tradit. Med. Formulae 2012, 18, 161(in Chinese). (吴莹, 金叶智, 张舒, 闫玥捷, 张津, 郝钰, 中国实验方剂学杂志, 2012, 18, 161.)
(b) Wu, Y.; Jin, Y. Z.; Wu, J.; Yu, X. F.; Hao, J. J. Beijing Univ. Trad. Chin. Med. 2010, 33, 541(in Chinese). (吴莹, 金叶智, 吴珺, 于雪飞, 郝钰, 北京中医药大学学报, 2010, 33, 541.)
[5] (a) Lee, H.; Kim, H.; Kim, S. Y.; Noh, H. S.; Kang, S. S.; Cho, G. J.; Choi, W. S.; Suk, A. K. FASEB J. 2003, 17, 1943.
(b) Wang, P. M.; Chen, W.; Meng, X. L. Chin. J. Exp. Tradit. Med. Formulae 2016, 22, 193(in Chinese). (王沛明, 陈文, 孟宪丽, 中国实验方剂学杂志, 2016, 22, 193.)
[6] (a) Ling, H.; Hua, M. Lishizhen Med. Mater. Med. Res. 2014, 25, 168(in Chinese). (凌芳, 华梅, 时珍国医国药, 2014, 25, 168.)
(b) Lee, S. O.; Jeong, Y. J.; Yu, M. H.; Lee, J. W.; Hwangbo, M. H.; Kim, C. H.; Lee, I. S. Biochem. Biophys. Res. Commun. 2006, 351, 122.
(c) Chang, Y. L.; Shen, J. J.; Wung, B. S. Mol. Pharmacol. 2001, 60, 512.
(d) Huang, H. C.; Wang, H. R.; Hsieh, L. M. Eur. J. Pharmacol. 1994, 251, 93.
(e) Huang, Z. D.; Liu, Y. M.; Kong, C. H.; Xie, X. R.; Fu, B. B. Int. J. Cerebrovasc. Dis. 2014, 22, 660(in Chinese). (黄正德, 刘煜敏, 孔朝红, 解晓睿, 付蓓蓓, 国际脑血管病杂志, 2014, 22, 660.)
[7] (a) Yan, J. Y.; Chen, B. A. Lishizhen Med. Mater. Med. Res. 2012, 23, 2210(in Chinese). (严静怡, 陈宝安, 时珍国医国药, 2012, 23, 2210.)
(b) Zhong, N.; Li, Q.; Feng, Y. H.; Gai, X.; Hao, L. Clin. Misdiagn. Misther. 2019, 32, 112(in Chinese). (种楠, 李勤, 冯艳红, 晁旭, 郝蕾, 临床误诊误治, 2019, 32, 112.)
(c) Polier, G.; Ding, J.; Konkimalla, B. V.; Eick, D.; Ribeiro, N.; Kohler, R.; Giaisi, M.; Efferth, T.; Desaubry, L.; Krammer, P. H.; Liweber, M. Cell Death Discovery 2011, 2, 182.
[8] (a) Xing, H.; Ning, C.; Kong, D. X.; Cai, H.; Zhou, S. Y.; Ren, C.; Kong, Y.; Cheng, J. X.; Chen, X. J. Chin. J. Clin. Pharmacol. Ther. 2019, 24, 889(in Chinese). (邢晗, 宁晨, 孔德璇, 蔡卉, 周时雨, 任畅, 孔颖, 程钰洁, 陈西敬, 中国临床药理学与治疗学, 2019, 24, 889.)
(b) Talbi, A.; Zhao, D.; Li, Q. W.; Li, J. X.; Fan, A. L.; Yang, W.; Han, X.; Chen, X. J. Molecules 2014, 19, 5538.
[9] (a) Li, G. J.; Zhao, K.; Yao, Y. Y.; Shen, L.; Guo, Q. L. J Chin Pharm Univ. 2015, 46, 464(in Chinese). (李国君, 赵凯, 姚彧远, 申乐, 郭青龙, 中国药科大学学报, 2015, 46, 464.)
(b) Li, L. W.; Lu, N.; Dai, Q. S.; Wei, L. B.; Zhao, Q.; Li, Z. Y.; He, Q. H.; Dai, Y.; Guo, Q. L. J. Ethnopharmacol. 2011, 13, 670.
[10] Zhao, L,; Miao, H. C.; Li, W. J.; Sun, Y.; Huang, S. L.; Li, Z. Y.; Guo, Q. L. Mol. Carcinog. 2016, 55, 778.
[11] Pan, D.; Li, W.; Miao, H.; Yao, J.; Li, Z. Y.; Wei, L. B.; Zhao, L.; Guo, Q. L. Biochem. Pharmacol. 2014, 87, 598.
[12] Zeng, S.; Liu, W.; Nie, F. F.; Zhao, Q.; Rong, J. J.; Wang, J.; Tao, L.; Qi, Q.; Lu, N.; Li, Z. Y.; Guo, Q. L. Biochem. Biophys. Res. Commun. 2009, 385, 551.
[13] Chen, Y.; Lu, N.; Ling, Y.; Wang, L.; You, Q. D.; Li, Z. Y.; Guo, Q. L. J. Pharmacol. Sci. 2010, 112, 37.
[14] Wang, J. B.; Ge, R. L.; Qiu, X. Q.; Xu, X.; Wei, L. B.; Li, Z. Y.; Bian, J. L. Eur. J. Med. Chem. 2017, 140, 421.
[15] Wang, J. B.; Li, T. H.; Zhao, T. T.; Wu, T. Z.; Ding, H.; Li, Z. Y. Eur. J. Med. Chem. 2019, 178, 782.
[16] Liu, W. Y.; Lin, L. X.; Zhang, Z. X. J. Chin. Pharm. Univ. 1997, 28, 162(in Chinese). (柳文媛, 林力行, 张正行, 中国药科大学学报, 1997, 28, 162.)
[17] Li, W. J.; Pan, X.; Chen, X. L.; Chen, W. Z.; Liao, L. M. Asia-Pacific Tradit. Med. 2014, 10, 33(in Chinese). (李文娟, 潘馨, 陈晓兰, 陈维中, 廖联明, 亚太传统医药, 2014, 10, 33.)
[18] Shah, R. C.; Mehta, C. R.; Wheeler, T. S. J. Chem. Soc. 1938, 1555.
[19] Rivailie, P.; Mentzer, C. J. Chem. Soc. 1969, 268, 2213.
[20] Huang, W. H.; Chien, P. Y.; Yang, C. H.; Lee, A. R. Chem. Pharm. Bull. 2003, 51, 339.
[21] Rao, K. V.; Seshadri, T. R.; Sc, F. A. Proc.-Indian Acad. Sci., Sect. A 1947, 26, 13.
[22] Li, T. H.; Weng, T. W.; Wang, J. B.; Wei, J. H.; Li, Z. Y. Org. Process Res. Dev. 2017, 21, 171.
[23] Yuan, H.; Ye, J.; Chen, H.; Zhao, Z.; Li, Y. Z.; Zhang, W. D.; Sun, Q. Y. Chin. J. Org. Chem. 2016, 36, 2960(in Chinese). (袁虎, 叶霁, 陈浩, 赵增, 李玉柱, 张卫东, 孙青龑, 有机化学, 2016, 36, 2960.)
[24] Seijas, J. A.; Vazquez-Tato, M. P.; Carballido-Reboredo, R. J. Org. Chem. 2005, 70, 2855.
[25] Caldwel, S. T.; Petersson, H. M.; Farrugia, L. J.; Mullen, W.; Crozier, A.; Hartley, R. C. Tetrahedron 2006, 62, 7257.
[26] (a) Kabalka, G. W.; Mereddy, A. R. Tetrahedron Lett. 2005, 46, 6315.
(b) Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115, 3358.
[27] Lu, K.; Chu, J.; Wang, H. M.; Fu, X. L.; Quan, D. W.; Ding, H. X.; Yao, Q. W.; Yu, P. Tetrahedron Lett. 2013, 54, 6345.
[28] Liger, F.; Pellet-Rostaing, S.; Popowycz, F.; Lemaire, M. Tetrahedron Lett. 2011, 52, 3736.
[29] Li, Z. Y.; Cao, X.; Wang, X.; Guo, Q. L.; You, Q. D. Org. Prep. Proced. Int. 2009, 41, 327.

汉黄芩素的方便合成

Efficient Synthesis of Wogonin

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