Chinese Journal of Organic Chemistry >
Concise Syntheses of 1,3-Dihydroxylxanthones and Their Clearance Effections against Nitrite
Received date: 2013-10-11
Revised date: 2013-11-10
Online published: 2013-11-21
Supported by
Project supported by the National Natural Science Foundation of China (No. 81172982), the Guangdong Provincial Project of Science and Technology (No. 2010A030100006) and the State Key Laboratory of Drug Research (No. SIMM1302KF-12).
Twelve 1,3-dihydroxylxanthones (3a～3l) were synthesized under the catalysis of Eaton's reagent applying phloroglucinol and substituted salicylic acids as starting materials. The yields were from 63% to 87%. The reaction mechanism and their structure-reaction activity relationship have been discussed. The clearance effections of all the prepared xanthones against nitrite have been investigated by UV spectrophotometry. It is disclosed that all the tested xanthones have obvious clearance effections against nitrite at the conditions of pH 3, room temperature, and 30 min treatment. 3b and 3f are identified as the most active compounds with clearance rate up to 34.0%. The clearance mechanism of xanthones against nitrite and their structure-activity relationships were also included here.
Key words： xanthones; organic synthesis; nitrite; cancer prevention; Eaton’s reagent
Mao Shuangshuang , Zheng Huanhuan , Luo Cuiting , Chen Heru . Concise Syntheses of 1,3-Dihydroxylxanthones and Their Clearance Effections against Nitrite[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 515 -521 . DOI: 10.6023/cjoc201310010
[1] Zhang, H.; Xu, G.; Yuan, J.-Y. J. Zhengzhou Grain College 2000, 21, 50 (in Chinese).
(张虹, 徐刚, 袁建耀, 郑州粮食学院学报, 2000, 21, 50.)
[2] Zhao, C.-H. Food Ind. 2010, 5, 4 (in Chinese).
(薛长晖, 食品工业, 2010, 5, 4.)
[3] Zhu, Y.-X.; Feng, H.-J.; Sun, Y. Cancer 1994, 13, 470 (in Chinese).
(褚衍信, 冯华进, 孙燕, 癌症, 1994, 13, 470.)
[4] Xiao, H.; Yang, L.; Zenai, C.; Guangming, L.; Jinfu, Q. J. Chin. Pharm. Sci. 2001, 10, 172.
[5] Ee, G. C. L.; Lim, C. K.; Lee, H. L. J. Asian Nat. Prod. Res. 2006, 8, 567.
[6] Wen, L.; Lin, Y.-C.; She, Z.-G.; Du, D.-S.; Chan, W.-L.; Zheng, Z. H. J. Asian Nat. Prod. Res. 2008, 10, 133.
[7] Nicole, P.; Panagiotis, M. Anti-Cancer Agents Med. Chem. 2009, 9, 77.
[8] Lesch, B.; Braese, S. Angew. Chem., Int. Ed. 2004, 43, 115.
[9] Sellés, A. J. N.; Castro, H. T. V.; Agüero, J.; González, J.; Naddeo, F.; De Simone, F.; Rastrelli, L. J. Agric. Food Chem. 2002, 50, 762.
[10] Luo, C.-T.; Mao, S.-S.; Liu, F.-L.; Yang, M.-X.; Chen, H.; Kurihara, H.; Li, Y. Fitoterapia 2013, 91, 140.
[11] Dube, M.; Zunker, K.; Neidhart, S.; Carle, R.; Steinhart, H.; Paschke, A. J. Agric. Food Chem. 2004, 52, 3938.
[12] Rukachaisirikul, V.; Kamkaew, M.; Sukavisit, D.; Taylor, W. C. J. Nat. Prod. 2003, 66, 1531.
[13] Park, H. H.; Park, Y.-D.; Han, J.-M.; Im, K.-R.; Lee, B. W.; Jeong, I. Y.; Jeong, T.-S.; Lee, W. S. Bioorg. Med. Chem. Lett. 2006, 16, 5580.
[14] Zhou, T.; Ohkoshi, E.; Bastow, K. F.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2012, 22, 3219.
[15] Masand, V. H.; Mahajan, D. T.; Patil, K. N.; Chinchkhede, K. D.; Jawarkar, R. D.; Hadda, T. B.; Alafeefy, A. A.; Shibi, I. G. Med Chem. Res. 2012, 21, 4523.
[16] Ichikib, H.; Okadab, M.; Ishidac, T.; Tanigawaa, K. Phytomedicine 2001, 8, 85.
[17] Zhang, X.-J.; Li, X.; Sun, H.-P.; Wang, X.-J.; Zhao, L.; Gao, Y.; Liu, X.-R.; Zhang, S.-L.; Wang, Y.-Y.; Yang, Y.-R.; Zeng, S.; Guo, Q.-L.; You, Q.-D. J. Med. Chem. 2013, 56, 276.
[18] Azevedo, C. M. G.; Afonso, C. M. M.; Sousa, D.; Lima, R. T.; Vasconcelos, M. H.; Pedro, M.; Barbosa, J.; Corrêa, A. G.; Reis, S.; Pinto, M. M. M. Bioorg. Med. Chem. 2013, 21, 2941.
[19] Peres, V.; Nagem, T. J.; De Oliveira, F. F. Phytochemistry 2000, 55, 683.
[20] Zou, H.; Koh, J.-J.; Li, J.-G.; Qiu, S.-X.; Aung, T. T.; Lin, H.-F.; Lakshminarayanan, R.; Dai, X.-P.; Tang, C.; Lim, F. H.; Zhou, L.; Tan, A. L.; Verma, C.; Tan, D. T. H.; Chan, H. S. O.; Saraswathi, P.; Cao, P.; Liu, S.-P.; Beuerman, R. W. J. Med. Chem. 2013, 56, 2359.
[21] Akrawi, O. A.; Mohammed, H. H.; Patonay, T.; Villinger, A.; Langer, P. Tetrahedron 2012, 68, 6298.
[22] Zou, Y.; Zhao, Q.-J.; Hu, H.-G.; Yu, S.-C.; Xu, M.-J.; Wu, Q.-Y. Arch. Pharm. Res. 2012, 35, 2093.
[23] Hu, L.-H.; Qin, Z.-L. Chin. J. Synth. Chem. 2002, 10, 285 (in Chinese).
(胡利红, 覃章兰, 合成化学, 2002, 10, 285.)
[24] Eaton, P. E.; Carlson, G. R.; Lee, J. T. J. Org. Chem. 1973, 38, 4071.
[25] Mehta, G.; Shah, S. R.; Venkataswarlu, Y. Tetrahedron 1994, 50, 11729.
[26] Horne, S.; Rodrigo, R. J. Org. Chem. 1990, 55, 4520.
[27] Alix, J.; Jiang, H. Wardlaq, J. H. Aust. J. Chem. 1990, 43, 1745.
[28] Yen, C.-T.; Nakagawa-Goto, K.; Hwang, T.-L.; Morris-Natschke, S. L.; Bastow, K. F.; Wu, Y.-C.; Lee, K.-H. Bioorg. Med. Chem. Lett. 2012, 22, 4018.
[29] Lin, C.-N.; Chung, M.-I.; Liou, S.-J.; Lee, T.-H.; Wang, J.-P. J. Pharm. Pharmacol. 1996, 48, 532.
[30] Ando, H.; Hirai, H.; Fujii, M.; Hori, Y.; Fukumura, M.; Niiho, Y.; Nakajima, Y.; Shibata, T.; Toriizuka, K.; Ida, Y. J. Nat. Med. 2007, 61, 269.
[31] Das, A.; Shaikh, M. M.; Jana, S. Med. Chem. Res. 2013, 1.
[32] Zhou, T.; Shi, Q.; Chen, C-H.; Huang, L.; Ho, P.; Morris-Natschke, L. S.; Lee, K.-H. Eur. J. Med. Chem. 2012, 47, 86.
[33] Pillai, R. K. M.; Naiksatam, P.; Johnson, F.; Rajagopalan, R.; Watts, P. C.; Cricchio, R.; Borras, S. J. Org. Chem. 1986, 51, 717.
[34] Markham, K. R. Tetrahedron 1965, 21, 1449.
[35] Cho, H.-J.; Jung, M.-J.; Woo, S.; Kim, J.; Lee, E.-S.; Na, Y. Bioorg. Med. Chem. 2010, 18, 1010.
[36] Song, R.; Wei, R.-B. Food Res. Dev. 2007, 28, 25 (in Chinese).
(宋茹, 韦荣编, 食品研究与开发, 2007, 28, 25.)
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