Application of Microwave Technique into Etherification of 10-Hydroxycamptothecin

doi:10.6023/cjoc201205025

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2378-2381.DOI: 10.6023/cjoc201205025 Previous Articles Next Articles

Notes

微波技术在10-羟基喜树碱醚化反应中的应用

孟光荣^a, 李嘉俊^a, 张倩^a, 马红梅^b

a 复旦大学药学院药物化学教研室上海 201203;
b 华东理工大学药学院上海 200237

收稿日期:2012-05-19 修回日期:2012-08-01 发布日期:2012-08-10
通讯作者: 马红梅 E-mail:hmma@ecust.edu.cn
基金资助:
创新药物平台(No. 2009ZX09301-011)资助项目.

Application of Microwave Technique into Etherification of 10-Hydroxycamptothecin

Meng Guangrong^a, Li Jiajun^a, Zhang Qian^a, Ma Hongmei^b

a Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203;
b School of Pharmacy, East China University of Science & Technology, Shanghai 200237

Received:2012-05-19 Revised:2012-08-01 Published:2012-08-10
Supported by:
Project supported by the National Drug Innovative Program (No. 2009ZX09301-011).

In an effort to reduce the cleavage of E lactone ring in camptothecin, microwave technique was applied in the etherification of 10-hydroxycamptothecin. Compared with the conventional heating condition, microwave can truncate the reaction time and improve the yield from 20%～30% to 50%～83% significantly. Furthermore, this reaction condition could be used for reference in other relative reactions of camptothecins.

Key words: 10-hydroxycamptothecin, etherification, microwave technology

Cite this article

Meng Guangrong, Li Jiajun, Zhang Qian, Ma Hongmei. Application of Microwave Technique into Etherification of 10-Hydroxycamptothecin[J]. Chin. J. Org. Chem., 2012, 32(12): 2378-2381.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Chu, W. China New Med. 2003, 2(6), 76 (in Chinese).
(褚伟, 中国新医药, 2003, 2(6), 76.)
[2] Fan, Y.; Weinstein, J. N.; Kohn, K. W. J. Med. Chem. 1998, 41, 2216.
[3] Crow, R. T.; Crothers, D. M. J. Med. Chem. 1992, 35, 4160.
[4] Song, Y. L.; Zhang, W. N.; Ji, H. T. Chin. Pharm. J. 2002, 37, 646 (in Chinese).
(宋云龙, 张万年, 季海涛, 中国药学杂志, 2002, 37, 646.)
[5] (a) Venditto, V. J.; Simanek, E. Mol. Pharm. 2010, 7, 307.
(b) Kingsbury, W. D.; Boehm, J. C.; Jakas, D. R.; Holden, K. G.; Hecht, S. M.; Gallagher, G.; Caranfa, M. J.; McCabe, F. L.; Faucette, L. F.; Johnson, R. K.; Hertzberg, R. P. J. Med. Chem. 1991, 344, 98.
(c) Kim, D. K.; Ryu, D. H.; Lee, J. Y.; Lee, N.; Kim, Y. W.; Kim, J. S.; Chang, K.; Im, G. J.; Kim, T. K.; Choi, W. S. J. Med. Chem. 2001, 44, 1594.
(d) Zu, Y. G,; Li, Q. Y.; Fu, Y. J.; Wang, W. Bioorg. Med. Chem. Lett. 2004, 14, 4023.
[6] (a) Lavergne, O.; Lesueur-Ginot, L.; Rodas, F. P.; Bigg, D. C. H. Bioorg. Med. Chem. Lett. 1997, 7, 2235.
(b) Du, W.; Curran, D. P.; Bevins, R. L.; Zimmer, S. G.; Zhang, J.; Burke, T. G. Bioorg. Med. Chem. 2002, 10, 103.
(c) Mao, L.; Wang, H.; Tan, M.; Ou, L.; Kong, D.; Yang, Z. Chem. Commun. 2012, 48, 395.
[7] Li, Q. Y.; Deng, X. Q.; Zu, Y. G.; Lv, H. Y.; Su, L.; Yao, L. P.; Zhang, Y.; Li, L. Eur. J. Med. Chem. 2010, 45, 3200.
[8] Li, Q. Y.; Zu, Y. G.; Shi, R. Z.; Yao, L. P.; Fu, Y. J.; Yang, Z. W.; Li, L. Bioorg. Med. Chem. Lett. 2006, 14, 7175.
[9] Li, Q. Y.; Zu, Y. G.; Fu, Y. J. Acta Pharm. Sin. 2004, 39, 521 (in Chinese).
(李庆勇, 祖元刚, 付玉杰, 药学学报, 2004, 39, 521.)
[10] Gedye, R.; Smith, F.; Westaway, K.; Ali, H. Tetrahedron Lett. 1986, 27(3), 279.
[11] Zhang, H. L.; Hu, X. M.; Lai, S. L. J. South China Univ. Technol. 1997, 25, 46 (in Chinese).
(张华莲, 胡希明, 赖声礼, 华南理工大学学报, 1997, 25, 46.)
[12] Fan, X. J.; You, J. M.; Tan, G. Z. Prog. Chem. 1998, 10(3), 285. Gao, M. Z.; Kathy, D. M.; George, W. S.; Qi, H. Z. Bioorg. Med. Chem. Lett. 2005, 15, 3865.

[1]	Lingna Wang, Xiaoqing Liu, Gang Lin, Hongying Jin, Minjun Jiao, Xuefen Liu, Shuping Luo. Photocatalytic Activation of C(sp³)—H Bonds to Form C—S Bonds Catalyzed by (Oxybis(4,1-phenylene))bis(phenylmethanone) [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2848-2854.
[2]	Xia Wang, Yixin Qu, Chengyu Long, Xue-Qiang Wang. Nucleophilic Etherification of Heteroaryl Alkyl Ethers, Heteroaryl Halides with (Deuterated) Alcohols [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 795-805.
[3]	Bowen Wang, Yongjun Zhou, Shihe Luo, Xiaoyan Luo, Weiqing Chen, Shimin Yang, Zhaoyang Wang. Research Progress in C—S Bond Formation Reaction of Olefins with Organic Sulfur Reagents under Photocatalyst-Free and Non-Electrochemical Conditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 171-184.
[4]	Yan Meng, Peng Wenchang, Wang Hui, Zhang Danwei, Li Zhanting. Supramolecular Organic Framework Loading for Camptothecin Open-Ring Carboxylates and Their Lactonization Kinetics [J]. Chin. J. Org. Chem., 2019, 39(9): 2567-2573.
[5]	Zhu Fuyuan, Wang Yanmei, He Mingchuang, Yan Zhaohua, Lin Sen. Tetrabutylammonium Iodide Promoted Thioetherification of Arylsulfonylhydrazides with 4-Hydroxycoumarins [J]. Chin. J. Org. Chem., 2019, 39(4): 1175-1180.
[6]	Jiang Haifang, Zhang Min, Zhang Li, Chen Yali, Zhu Ning, Song Liping, Deng Hongmei. Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives [J]. Chin. J. Org. Chem., 2017, 37(9): 2399-2408.
[7]	Fan Weiyong, Yu Lei, Peng Xiangjun, Liu Liangxian. In the Presence of FeCl₃ Reaction of Alknols with Iodine: A Convenient Synthetic Route to Iodocyclic Ethers [J]. Chin. J. Org. Chem., 2017, 37(4): 920-924.
[8]	Guan Litao, Mo Guangzhen, Wu Yancheng, Liang Xinyu, Luo Qiaofang, Wang Zhaoyang. Synthesis of 2(5H)-Furanone Derivatives with Biphenyl Ether Unit [J]. Chin. J. Org. Chem., 2015, 35(5): 1081-1089.
[9]	Yan Zhaohua, Yu Xinquan, Liu Yongjie, Xu Yun, Lin Sen. Etherification of 2-Acetoxymethylpyrrole Derivative with Alcohol Catalyzed by para-Toluenesulfonic Acid [J]. Chin. J. Org. Chem., 2013, 33(9): 1975-1981.
[10]	Zuo Hujin, Zhang Lei, Wu Changzhi, Wang Chengyun, Shen Yongjia. Synthesis of 3,4-Ethylenedioxythiophene Substituted with Hydroxymethyl and Iodomethyl Groups and Their Selective Esterification and Etherification [J]. Chin. J. Org. Chem., 2013, 33(01): 148-153.
[11]	Yan Zhaohua, Yu Zhangxin, Liu Yongjie, Hu Wei. Etherification of 2-Acetoxymethylpyrrole Derivative with Sodium Alkoxide [J]. Chin. J. Org. Chem., 2012, 32(10): 1965-1969.
[12]	TU Kai-Hui, ZHANG Xiao-Li, HU Jiao-Sheng, LIU Liang-Xian. FeCl₃ Reaction of Alkynols with Iodine: Convenient Synthetic Route to Iodocycloenol Ethers [J]. Chin. J. Org. Chem., 2010, 30(02): 266-271.
[13]	LI Ji-Tai*,LI Xiao-Liang,LIU Xian-Feng,MA Jie-Jie. Synthesis of O-Benzyloximes by Combination of Phase Transfer Catalysis and Ultrasound Irradiation [J]. Chin. J. Org. Chem., 2008, 28(04): 628-631.
[14]	ZHU, Lei^a,b,CAO, De-Rong^*,a,3,GAO, Chun-Mei^a,b Monoetherification of 9,10-Bishydroxymethylanthracene)tin Arylcarboxylates [J]. Chin. J. Org. Chem., 2006, 26(06): 848-851.
[15]	LIANG Jian-Hua,YAO Guo-Wei*. An Improvement for the Synthesis of Clarithromycin [J]. Chin. J. Org. Chem., 2005, 25(04): 438-441.

微波技术在10-羟基喜树碱醚化反应中的应用

Application of Microwave Technique into Etherification of 10-Hydroxycamptothecin

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments