Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues

doi:10.6023/cjoc201204001

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2141-2147.DOI: 10.6023/cjoc201204001 Previous Articles Next Articles

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查尔酮及其螺杂环衍生物的合成、晶体结构、抗氧化活性研究

吴建章^a,b, 李物兰^c, 陈玲姿^b, 楚生辉^b, 赵承光^a, 卫涛^b, 杨树林^a, 李校堃^a,b

a 南京理工大学生物工程研究所南京 210094;
b 温州医学院药学院温州 325035;
c 温州医学院信息与工程学院温州 325035

收稿日期:2012-04-01 修回日期:2012-06-18 发布日期:2012-07-02
通讯作者: 杨树林 E-mail:wjzwzmc@126.com, wujianzhang6@163.com
基金资助:
浙江省医药卫生科技计划(No. 2012KYA129)、温州市科技局(No. Y20090101)、浙江省中医药科技计划B类(No. 2012ZB102)资助项目.

Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues

Wu Jianzhang^a,b, Li Wulan^c, Chen Lingzi^b, Chu Shenghui^b, Zhao Chenguang^a, Wei Tao^b, Yang Shulin^a, Li Xiaokun^a,b

a Institute of Biotechnology, Nanjing University of Science and Technology, Nanjing 210094;
b School of Pharmacy, Wenzhou Medical College, Wenzhou 325035;
c College of Information Science and Computer Engineering, Wenzhou Medical College, Wenzhou 325035

Received:2012-04-01 Revised:2012-06-18 Published:2012-07-02
Supported by:
Project supported by the Technology Foundation for Medical Science of Zhejiang Province (No. 2012KYA129), the Project of Wenzhou Sci & Tech Bureau (No. 20090101), and the Technology Foundation for Chinese Medicine of Zhejiang Province (No. 2012ZB102).

To synthesize new structure type chalcone analogues, and obtain chalcone analogues with good antioxidant activity. Two types of chalcone analogs, chalcones A and spiro-heterocyclic B were designed and synthesized, and the structures of 21 compounds were characterized by ¹H NMR, ESI-MS and ESI-HRMS. Single-crystal of spiro-heterocyclic B was cultured, and its single-crystal structure was determined by X-ray diffraction study. The crystal structure of B1 was monoclinic system, space group C2/c, with cell dimensions of a＝21.350(3) Å, b＝8.6256(10) Å, c＝26.161(3) Å. Spiro-heterocyclic B is the new structure type, and obtained by one-pot synthesis which is 1,3-dipolar cycloaddition reaction and no catalyst. The synthesis of spiro-heterocyclic B is not only high regioselectivity and stereoselectivity, but also environmentally friendly. The antioxidant activities in vitro were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Many compounds, which can have strong activity of scavenging DPPH free radicals, were screened. In the 2 types of chalcones analogs, the compounds with 3,4-(OH)₂ in “a” ring have excellent antioxidant activities. The chalcone analogs with o-dihydroxy in benzene ring maybe have good antioxidant activities.

Key words: chalcones, spiro-heterocyclic, synthesis, DPPH, antioxidant activities, crystal structure

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Wu Jianzhang, Li Wulan, Chen Lingzi, Chu Shenghui, Zhao Chenguang, Wei Tao, Yang Shulin, Li Xiaokun. Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues[J]. Chin. J. Org. Chem., 2012, 32(11): 2141-2147.

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References

[1] Cioffi, G.; Morales Escobar, L.; Braca, A.; De Tommasi, N. J. Nat. Prod. 2003, 66, 1061.

[2] Wu, J. Z.; Li, J. L.; Cai, Y. P.; Pan, Y.; Ye, F. Q.; Zhang, Y. L.; Zhao, Y. J.; Yang, S. L.; Li, X. K.; Liang, G. J. Med. Chem. 2011, 54: 8110.

[3] Martens, S.; Mithofer, A. Phytochemistry 2005, 66, 2399.

[4] Chen, Z. H.; Zheng, C. J.; Sun, L. P.; Piao, H. R. Eur. J. Med. Chem. 2010, 45, 5739.

[5] Dominguez, J. N.; Leon, C.; Rodrigues, J.; Gamboa de Dominguez, N.; Gut, J.; Rosenthal, P. J. J. Med. Chem. 2005, 48, 3654.

[6] Guantai, E. M.; Ncokazi, K.; Egan, T. J.; Gut, J.; Rosenthal, P. J.; Bhampidipati, R.; Kopinathan, A.; Smith, P. J.; Chibale, K. J. Med. Chem. 2011, 54, 3637.

[7] Ghosh, A.; Mandal, S.; Banerji, A.; Kar, M.; Banerji, J. Nat. Prod. Commun. 2009, 4, 209.

[8] Kozlowski, D.; Trouillas, P.; Calliste, C.; Marsal, P.; Lazzaroni, R.; Duroux, J. L. J. Phys. Chem. A 2007, 111, 1138.

[9] Padhye, S.; Ahmad, A.; Oswal, N.; Sarkar, F. H. J. Hematol. Oncol. 2009, 2, 38.

[10] Kumar, R. R.; Perumal, S.; Senthilkumar, P.; Yogeeswari, P.; Sriram, D. J. Med. Chem. 2008, 51, 5731.

[11] Sogawa, S.; Nihro, Y.; Ueda, H.; Izumi, A.; Miki, T.; Matsumoto, H.; Satoh, T. J. Med. Chem. 1993, 36, 3904.

[12] Iwata, S.; Nishino, T.; Nagata, N.; Satomi, Y.; Nishino, H.; Shibata, S. Biol. Pharm. Bull. 1995, 18, 1710.

[13] Lopez, S. N.; Castelli, M. V.; Zacchino, S. A.; Dominguez, J. N.; Lobo, G.; Charris-Charris, J.; Cortes, J. C.; Ribas, J. C.; Devia, C.; Rodriguez, A. M.; Enriz, R. D. Bioorg. Med. Chem. 2001, 9, 1999.

[14] Bag, S.; Ramar, S.; Degani, M. S. Med. Chem. Res. 2009, 18, 309.

[15] Guantai, E. M.; Ncokazi, K.; Egan, T. J.; Gut, J.; Rosenthal, P. J.; Bhampidipati, R.; Kopinathan, A.; Smith, P. J.; Chibale, K. J. Med. Chem. 2011, 54, 3637.

[16] Hsieh, H. K.; Lee, T. H.; Wang, J. P.; Wang, J. J.; Lin, C. N. Pharm. Res. 1998, 15, 39.

[17] Gul, H. I.; Yerdelen, K. O.; Das, U.; Gul, M.; Pandit, B.; Li, P. K.; Dimmock, J. R. Chem. Pharm. Bull. (Tokyo) 2008, 56, 1675.

[18] Acharya, B. N.; Saraswat, D.; Tiwari, M.; Shrivastava, A. K.; Ghorpade, R.; Bapna, S.; Kaushik, M. P. Eur. J. Med. Chem. 2010, 45, 430.

[19] Zhang, X. W.; Zhao, D. H.; Quan, Y. C.; Sun, L. P.; Yin, X. M.; Guan., L. P. Med. Chem. Res. 2010, 19, 403.

[20] Viqar, U. A.; Mohammad, G. S.; Mushtaq, N.; Mohammad, F. V. J. Nat. Prod. 1992, 55, 956. Kumar, R. R.; Perumal, S.; Senthilkumar, P.; Yogeeswari, P.; Sriram, D. Tetrahedron 2008, 64, 2962.

查尔酮及其螺杂环衍生物的合成、晶体结构、抗氧化活性研究

Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues

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