Synthesis of ArSe-Substituted Flavone Derivatives Using Se Powder

doi:10.6023/cjoc201808011

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1187-1192.DOI: 10.6023/cjoc201808011 Previous Articles Next Articles

Notes

Se粉为原料的芳硒基取代黄酮衍生物的合成

冯春来, 朱杰, 唐秋洁, 周爱华

江苏大学药学院镇江 212013

收稿日期:2018-08-10 修回日期:2018-09-20 发布日期:2018-11-12
通讯作者: 周爱华 E-mail:ahz@ujs.edn.cn
基金资助:
江苏大学（No.1281290006）资助项目.

Synthesis of ArSe-Substituted Flavone Derivatives Using Se Powder

Feng Chunlai, Zhu Jie, Tang Qiujie, Zhou Aihua

Pharmacy School, Jiangsu University, Zhenjiang 212013

Received:2018-08-10 Revised:2018-09-20 Published:2018-11-12
Contact: 10.6023/cjoc201808011 E-mail:ahz@ujs.edn.cn
Supported by:
Project supported by Jiangsu University (No. 1281290006).

New flavone derivatives are highly valued in drug discovery due to their diversity of important bioactivities. Herein, one simple Cu-catalyzed method of constructing C-Se bonds on flavone structures using convenient Se powder via C-H functionalization is reported, regioselectively affording ArSe-substituted flavone derivatives in good yields.

Key words: selenium, C—Se bond, flavone, selenide, C—H functionalization

Cite this article

Feng Chunlai, Zhu Jie, Tang Qiujie, Zhou Aihua. Synthesis of ArSe-Substituted Flavone Derivatives Using Se Powder[J]. Chin. J. Org. Chem., 2019, 39(4): 1187-1192.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Espargaro, A.; Ginex, T.; Vadell, M. D.; Busquets, M. A.; Estelrich, J.; Munoz-Torrero, D.; Luque, F. J.; Sabate, R. J. Nat. Prod. 2017, 80, 278.
(b) Tsou, L. K.; Lara-Tejero, M.; RoseFigura, J.; Zhang, Z. J.; Wang, Y. C.; Yount, J. S.; Lefebre, M.; Dossa, P. D.; Kato, J.; Guan, F.; Lam, W.; Cheng, Y. C.; Galan, J. E.; Hang, H. C. J. Am. Chem. Soc. 2016, 138, 2209.
(c) Cragg, G. M.; Grothaus, P. G.; Newman, D. J. Chem. Rev. 2009, 109, 3012.
[2] (a) Chen, H.; Olatunji, O. J.; Zhou, Y. J. Nat. Med. 2016, 70, 610.
(b) Zhou, Z.; Tang, M.; Liu, Y.; Zhang, Z.; Lu, R.; Lu, J. An-ti-Cancer Drugs 2017, 28, 446.
(c) Gaspar, A.; Matos, M. J.; Garrido, J.; Uriarte, E.; Borges, F. Chem. Rev. 2014, 114, 4960.
[3] (a) Kim, Y.-W.; Hackett, J. C.; Brueggemeier, R. W. J. Med. Chem. 2004, 47, 4032.
(b) Francisco, V.; Figueirinha, A.; Costa, G.; Liberal, J.; Ferreira, I.; Lopes, M. C.; García-Rodríguez, C.; Cruz, M. T.; Batista, M. T. J. Nat. Prod. 2016, 79, 1423.
(c) Wang, Q.; Du, X.; Zhou, B.; Li, J.; Lu, W.; Chen, Q.; Gao, J. Biomed. Pharmacother. 2017, 96, 396.
(d) Van Acker A. A. F.; Hageman, A. J.; Haenen R. M. M. G.; Van der Vijgh J. F. W.; Bast, A.; Menge, M. P. B. W. J. Med. Chem. 2000, 43, 3752.
(e) Lin, S.; Koh, J.-J.; Aung, T. T.; Ling, W.; Sin, W.; Lim, F.; Wang, L.; Lakshminarayanan, R.; Zhou, L.; Tan, D.; Cao, D.; Beuerman, R. W.; Ren, L.; Liu S. J. Med. Chem. 2017, 60, 6152.
(f) Ribeiro, A.; Piló-Veloso, D.; Romanha, A. J.; Carlos, L.; Zani, C. J. Nat. Prod. 1997, 60, 836.
[4] (a) Qiu, L.; Chen, K. Fitoterapia 2013, 84, 140.
(b) Lu, Y.; Zhang, R.; Liu, S.; Zhao, Y.; Gao, J.; Zhu, L. Eur. J. Pharmacol. 2016, 771, 130.
(c) Zheng, W.; Huang, Y. J. Med. Chem. Commun. 2014, 5, 297.
(d) Xie, M.; Xu, Y.; Shen, H.; Shen, S.; Ge, Y.; Xie, J. Int. J. Pharm. 2014, 474, 223.
(e) Zhang, X. P.; Miao, J. H.; Sun, Y. B. Chin. J. Org. Chem. 2009, 29, 1555(in Chinese). (张晓鹏, 苗江欢, 孙玉标, 有机化学, 2009, 29, 1555.)
(f) Qiu, L. P.; Chen, K. P. Fitoterapia 2013, 84, 140.
(g) Lu, Y. P.; Zhang, R.; Liu, S. Y.; Zhao, Y.; Gao, J.; Zhu, L. Eur. J. Pharmacol. 2016, 771, 130.
[5] (a) Shirizi, A. N.; Tiwari, R.; Oh, D.; Sullivan, S.; Kumar, A.; Beni, Y.; Parang, K. Mol. Pharmaceutics 2014, 11, 3631.
(b) Cao, S.; Durrani, F. A.; Rustum, Y. M. Clin. Cancer Res. 2004, 10, 2561.
(c) Madhunapantula, S. V.; Desai, D.; Sharma, A.; Huh, S. J.; Amin, S.; Robertson, G. P. Mol. Cancer. Ther. 2008, 7, 1297.
(d) Liu, M.; Li, Y.; Yu, L.; Xu, Q.; Jiang, X. Sci. China, Chem. 2018, 61, 294.
(e) Yu, L.; Wu, Y.; Chen, T.; Pan, Y.; Xu, Q. Org. Lett. 2013, 15, 144.
(f) Jing, X.; Yuan, D.; Yu, L. Adv. Synth. Catal. 2017, 359, 1194.
(g) Wang, Y.; Yu, L.; Zhu, B.; Yu, L. J. Mater. Chem. A 2016, 4, 10828.
(h) Yu, L.; Chen, F.; Ding, Y. ChemCatChem 2016, 8, 1033.
(i) Yu, L.; Li, H.; Zhang, X.; Ye, J.; Liu, J.; Xu, Q.; Lautens, M. Org. Lett. 2014, 16, 1346.
[6] (a) Zhao, W. N.; Xie, P.; Bian, Z. G.; Zhou, A. H.; Ge, H.; Zhang, M.; Ding, Y.; Zheng, L. J. Org. Chem. 2015, 80, 9167.
(b) Niu, B.; Zhao, W. N.; Ding, Y. C.; Bian, Z.; Pittman, C. U. Jr.; Zhou, A. H.; Ge, H. J. Org. Chem. 2015, 80, 7251.
(c) Yatabe, T.; Jin, X.; Mizuno, N.; Yamaguchi, K. ACS Catal. 2018, 8, 4969.
(d) Zhao, X.; Zhou, J.; Lin, S.; Jin, X.; Liu, R. Org. Lett. 2017, 19, 976.
(e) Yang, Y. Q. Nat. Prod. Res. 2016, 30, 1628.
[7] (a) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
(b) Thanna, S.; Goins, C. M.; Knudson, S. E.; Slayden, R. A.; Ronning, D. R.; Sucheck, S. J. J. Org. Chem. 2017, 82, 3844.
(c) Arisawa, M.; Fujimoto, K.; Morinaka, S.; Yamaguchi, M. J. Am. Chem. Soc. 2005, 127, 12226.
(d) Joussot, J.; Schoenfelder, A.; Larquetoux, L.; Nicolas, M.; Suffert, J.; Blond, J. Synthesis 2016, 48, 3364.
(e) Chen, J.; Zhou, X. J. Chin. J. Org. Chem. 1987, 7, 331(in Chinese). (陈坚, 周洵钧, 有机化学, 1987, 7, 331.)
(f) Zheng, W. P. Mini-Rev. Med. Chem. 2013, 13, 132.
[8] (a) Zhao, W. N.; Xie, P.; Bian, Z. G.; Zhou, A. H.; Ge, H.; Niu, B.; Ding, Y. C. RSC Adv. 2015, 5, 59861.
(b) Shi, L.-F.; Zhang, X.-G.; Zhang, X.-H. Tetrahedron 2016, 72, 8617.
[9] (a) Alla, S. K.; Sadhu, P.; Punniyamurthy, T. J. Org. Chem. 2014, 79, 7502.
(b) Qin, Y.; Zhu, L.; Luo, S. Chem. Rev. 2017, 117, 9433.
(c) Yuan, R.; Wang, Y. J.; Huang, S. Y.; Dou, P. F.; Zhang, L. Y.; Chen, W.; Ren, X. X.; Zhou, S. L.; Wan, Y.; Wu, H. Chin. J. Org. Chem. 2018, 38, 3338(in Chinese). (苑睿, 王园江, 黄树颖, 窦鹏飞, 张珑严, 陈雯, 任璇璇, 周生亮, 宛瑜, 吴翚, 有机化学, 2018, 38, 3338.)
[10] (a) Rafique, J.; Saba, S.; Schneider, A. R.; Franco, M. S.; Silva, S. M.; Braga, A. L. ACS Omega 2017, 2, 2280.
(b) Zhong, S.; Liu, Y.; Cao, X.; Wan, J.-P. ChemCatChem 2017, 9, 465.
(c) Benhur, G.; Adriane, S.; Bruning, C. A.; Back, D. F.; Henrique, M., P.; Nogueira, C. W.; Zeni, G. Adv. Synth. Catal. 2011, 353, 2042.
[11] (a) Min, L.; Wu, G.; Liu, M.; Gao, W.; Ding, J.; Chen, J.; Huang, X.; Wu, H. J. Org. Chem. 2016, 81, 7584.
(b) Gao, C.; Wu, G.; Min, L.; Liu, M.; Gao, W.; Ding, J.; Chen, J.; Huang, X.; Wu, H. J. Org. Chem. 2017, 82, 250.
[12] Tang, Q.; Bian, Z.; Wu, W.; Wang, J.; Xie, P.; Pittman, C. U., Jr.; Zhou, A. J. Org. Chem. 2017, 82, 10617.
[13] (a) Stubbing, L.; Li, F.; Furkert, D.; Caprio, V.; Brimble, M. Tetrahedron 2012, 68, 6948.
(b) Yang, Y.; Qi, X.; Liu, R.; He, Q.; Yang, C. RSC Adv. 2016, 6, 103895.
(c) Jaen, J.; Wise, L.; Heffner, T.; Pugsley, T.; Meltzer, L. J. Med. Chem. 1991, 34, 248.
(d) He, Q.; So, C.; Bian, Z.; Hayashi, T.; Wang, J. Chem.-Asian J. 2015, 10, 540.
[14] Ding, Y. C.; Wu, W.; Zhao, W. N.; Li, Y.; Xie, P.; Huang, Y.; Liu, Y.; Zhou, A. H. Org. Biomol. Chem. 2016, 14, 1428.
[15] (a) Mohan, B.; Hwang, S.; Woo, H.; Park, K. H. Tetrahedron 2014, 70, 2699.
(b) Soleiman-Beiji, M.; Yavari, I.; Sadeghizadeh, F. RSC Adv. 2015, 5, 87564.
(c) Li, Z.; Ke, F.; Deng, H.; Xu, H.; Xiang, H.; Zhou, X. Org. Biomol. Chem. 2013, 11, 2943.
(d) Singh, D.; Deobald, A. M.; Camargo, L. S.; Tabarelli, G.; Rodrigues, O. D.; Braga, A. Org. Lett. 2010, 12, 3288.
(e) Guo, T. Synth. Commun. 2017, 47, 2053.

Se粉为原料的芳硒基取代黄酮衍生物的合成

Synthesis of ArSe-Substituted Flavone Derivatives Using Se Powder

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Zhangyang Shen, Yujie Li, Yimeng Zhao, Yayuan Deng, Yawen Guo, Yu Wang, Yanping Liu, Yanhui Fu. A New Prenylated Isoflavone from the Stems of Harrisonia perforata [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 771-776.
[2]	Siyi Zhou, Xu Ding, Yongmei Zhao, Jinghua Li, Wen Luo. A Flavone-Based Long-Wavelength Fluorescent Probe to Detect Biothiols in vitro and in vivo [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 178-185.
[3]	Wenjian Zhou, Xinrui Xiao, Yonghong Liu, Xu Zhang. Magnetic Se/Fe/PCN-Catalyzed Oxidative Cracking Alkenes in O₂ [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1849-1855.
[4]	Fei Yuan, Yan Zhao, Qingsong Guo, Fudan Yin, Jinrong Lai, Beifang Nian, Ming Zhang, E Tang. Synthesis of 1-[1-(Amino)cyclopropyl]ketones by Tandem Reaction Involving Vinyl Selenium Salt [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1759-1769.
[5]	Yifan Yin, Chen Li, Kai Sun, Yingjie Liu, Xin Wang. Radical Aminoselenation of Styrenes: Facile Access to β-Amido-selenides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1431-1437.
[6]	Liming Wang, Ke Li, Wanxuan Zhang. Organoselenium-Catalyzed Conversion of Oximes to Nitriles or Ketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1235-1240.
[7]	Shan Li, Yuan Cao, Lüqi Jiang. Recent Progress on Alkyl-, Aryl- and Fluoroalkyl-selenylation Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 434-457.
[8]	Tingting Yu, Dongxue Song, Ying Xu, Bing Liu, Ning Chen, Yingjie Liu. Study on the Application of Thios/Selenium Sulfonates as Radical Reagent [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4202-4219.
[9]	Hong'en Cao, Peizi Li, Xiaobi Jing, Hongwei Zhou. Selective Epoxidation of β-Ionone Catalyzed by Iron-Doped Se/C [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3890-3895.
[10]	Yunqian Zhang, Chenfan Zhou, Gongqing Liu. tert-Butyl Hydroperoxide-Mediated Synthesis of Phosphoroselenoates [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 218-225.
[11]	Ningbo Li, Li Xu, Rong Ma, Qi Fan, Bo Li, Jie Qiao, Rui Guo, Xinhua Xu. Synthesis and Antitumor Activities of Novel Organic Sulfur (Selenium) Tegafur Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2723-2734.
[12]	Feng Liu, Jie Zhan, Yangyang Sun, Xiaobi Jing. Silver Selenide as the Novel Catalytic Material for Alcohol Oxidation [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2099-2104.
[13]	Jiejun Huang, Rongrong Qian, Shuang Wang, Hong'en Cao. Polyselenide-Catalyzed Cyclohexene Oxidation to Produce 1,2-Cyclohexanediol [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1639-1645.
[14]	Ying Xu, Chen Li, Jianping Meng, Yuling Huang, Jiyuan Fu, Bing Liu, Yingjie Liu, Ning Chen. Recent Progress in the Selenocyclization Reactions with Organic Selenides [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1012-1030.
[15]	Yanhui Fu, Yutong Xie, Qingwei Ma, Bo Jiang, Lan Xie, Zehua Qiao, Yanping Liu. A New Prenylated Isoflavone from the Stems and Leaves of Trigonostemon howii [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1246-1250.