Photocatalysis Synthesis and Cytotoxicity of α-Santonin Rearrangement Derivatives

doi:10.6023/cjoc201505020

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2142-2149.DOI: 10.6023/cjoc201505020 Previous Articles Next Articles

Articles

α-山道年光催化重排衍生物的制备及细胞毒活性研究

戴笑丽^a, 汤建^a, 章凌琼^b, 陶连芝^b, 欧阳臻^a, 王民^b

a 江苏大学药学院镇江 212013;
b 杭州师范大学材料与化学化工学院杭州 310036

收稿日期:2015-05-11 修回日期:2015-06-08 发布日期:2015-06-12
通讯作者: 欧阳臻, 王民 E-mail:zhenouyang@ujs.edu.cn;mwang@hznu.edu.cn
基金资助:
国家自然科学基金(Nos. 21372056, 21202027)资助项目.

Photocatalysis Synthesis and Cytotoxicity of α-Santonin Rearrangement Derivatives

Dai Xiaoli^a, Tang Jian^a, Zhang Lingqiong^b, Tao Lianzhi^b, Ouyang Zhen^a, Wang Min^b

a School of Pharmacy, Jiangsu University, Zhenjiang 212013;
b College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036

Received:2015-05-11 Revised:2015-06-08 Published:2015-06-12
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21372056, 21202027).

1. Photocatalysis Synthesis and Cytotoxicity of α-Santonin Rearrangement Derivatives.PDF(3410KB)

Abstract

20 guaianolide derivatives 1～20 and 6-epi-santonin were synthesized from α-santonin through rearrangement, oxidation, and reduction, hydrolysis. The structures of all compounds were characterized by ¹H NMR, ¹³C NMR and MS. The cell proliferation inhibiting activities of the target compounds were evaluated against A549 and HepG2 cell lines by thiazolyl blueterazolium bromide (MTT) method. The results showed that the epoxy guaiane 9 had obvious inhibitory effect on A549 and HepG2 cell lines with IC₅₀ values of (14.5±0.1), (10.6±0.3) μmol/L while epoxy guaiane 15 showed IC₅₀ values of (6.4±1.3) and (8.1±0.7) μmol/L.

Key words: α-santonin, guaiane, derivative, cytotoxicity

Cite this article

Dai Xiaoli, Tang Jian, Zhang Lingqiong, Tao Lianzhi, Ouyang Zhen, Wang Min. Photocatalysis Synthesis and Cytotoxicity of α-Santonin Rearrangement Derivatives[J]. Chin. J. Org. Chem., 2015, 35(10): 2142-2149.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Wu, L. J. Textbook of Medicinal Chemistry of Natural Products, People's Medical Publishing House, Beijing, 2007, pp. 227～232 (in Chinese). (吴立军, 天然药物化学教材, 人民卫生出版社, 北京, 2007, pp. 227～232.)
[2] Saxena, V. K.; Mondal, S. K. Phytochemistry 1994, 35, 1080.
[3] Qian, M. K.; Zhu, D. Y. Pharm. Bull. 1979, 17, 277 (in Chinese ). (钱名堃, 朱大元, 药学通报, 1979, 17, 277.)
[4] Bruno, M.; Rosselli, S.; Maggio, A.; Raccuglia, R. A.; Bastow, K. F.; Lee, K. H. J. Nat. Prod. 2005, 68, 1042.
[5] René, C.; Anke, H.; Bianka, S.; Stefan, S.; Alexander, B.; Ralph, K.; Dieter, S. Pharm. Chem. Life Sci. 2012, 345, 215.
[6] Francisco, A. M.; Alejandro, S.; Azusa, Y.; Rosa, M., V.; Frank, R. F.; José, M. G. M. J. Nat. Prod. 2012, 75, 1967.
[7] Park, K. H.; Yang, M. S.; Park, M. K.; Kim, S. C.; Yang, C. H.; Park, S. J.; Lee, J. R. Fitoterapia 2009, 80, 54.
[8] Usuki, T.; Sato, M.; Hara, S.; Yoshimoto, Y.; Kondo, R.; Zimmermann, S.; Kaiser, M.; Brun, R.; Hamburger, M.; Adams, M. Bioorg. Med. Chem. Lett. 2014, 24, 794.
[9] Zhang, W. H.; Luo, S. J.; Fang, F.; Chen, C. S.; Hu, H. W.; Jia, X. S.; Zhai, H. B. J. Am. Chem. Soc. 2005, 127, 18.
[10] Li, C.; Dong, T.; Li, Q.; Lei, X. Angew. Chem., Int. Ed. 2014, 53, 12111.
[11] Li, C.; Yu, X. L.; Lei, X. G. Org. Lett. 2010, 12, 4284.
[12] Xia, W.-J.; Sun, L.-D.; Shi, L.; Zhang, S.-Y.; Tu, Y.-Q. Chin. J. Chem. 2004, 22, 377.
[13] Li, D. R.; Xia, W. J.; Shi, L.; Tu, Y. Q. Synthesis 2003, 41.
[14] Xia, W. J.; Tu, Y. Q.; Li, D. R. Synth. Commun. 2001, 31, 1613.
[15] Xia, D.; Du Y.; Yi, Z.; Song, H.; Qin, Y. Chem.-Eur. J. 2013, 19, 4423.
[16] Bargues, V.; Blay, G.; Cardona, L.; Garcia, B.; Pedro, J. R. Tetrahedron 1998, 54, 1845.
[17] Arantes, F. F. P.; Barbosa, L. C. A.; Alvarenga, E. S.; Demuner, A. J.; Bezerra, D. P.; Ferreira, J. R. O.; Costa-Lotufo, L. V.; Pessoa, C.; Moraes, M. O. Eur. J. Med. Chem. 2009, 44, 3739.
[18] Andrew, E. G.; Mark, T. E. J. Org. Chem. 1989, 54, 1468.
[19] Peter, M.; Simon, B.; Roland, F. J. Am. Chem. Soc. 1993, 115, 12595.
[20] Blay, G.; Cardona, L.; Garcia, B.; Lahoz, L.; Pedro, J. R. J. Org. Chem. 2001, 66, 7700.
[21] Makiyi, E. F.; Frade, R. F. M.; Lebl, T.; Jaffray, E. G.; Cobb, S. E.; Harvey, A. L.; Slawin, A. M. Z.; Hay, R. T.; Westwood, N. J. Eur. J. Org. Chem. 2009, 5711.
[22] Ando, M.; Akahane, A.; Yamaoka, H.; Takase, K. J. Org. Chem. 1982, 47, 3909.

α-山道年光催化重排衍生物的制备及细胞毒活性研究

Photocatalysis Synthesis and Cytotoxicity of α-Santonin Rearrangement Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Lijun Xu, Zongjun Li, Fushe Han, Xiang Gao. N,N-Dimethylformamide-Promoted Synthesis of Fullerene-Fused Oxazoline Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 242-250.
[2]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[3]	Xiaoke Zhang, Xiangru Zheng, Chaoyong Wang. Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3180-3187.
[4]	Xuedan Wu, Ruixiang Xu, Xiaolong Fang, Kehua Zhang, Jie Jin. Design and Synthesis of N-Tetrazole and N-Oxadiazole Heterocyclic Derivatives of Sinomenine [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2506-2518.
[5]	Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.
[6]	Yongzhou Pan, Xiujin Meng, Yingchun Wang, Muxue He. Recent Progress in Electrochemical Fixation of CO₂ to Construct Carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1416-1434.
[7]	Qifan Wang, Yuanquan Zhang, Li Xing, Yuanxiang Zhou, Chenyu Gong, Bangcan He, Nian Zhang, Yongjun Wu, Wei Xue. Design, Synthesis and Biological Activity of Myricetin Derivatives Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1525-1536.
[8]	Shenhao Chen, Song Zou, Chanjuan Xi. Photocatalyzed 2∶2 Coupling of Styrene and BrCF₂CO₂Me: A Facile Synthesis of Bis-difluoroacetylated Hexestrol Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1157-1167.
[9]	Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293.
[10]	Peng Zhou, Weiming Zhu, Jiantao Zhang, Duoduo Xiao, Xiangfeng Guo, Weibing Liu. Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3939-3944.
[11]	Meijiao Sun, Jing Tan, Yu Tan, Jinsong Peng, Chunxia Chen. Pd-Catalyzed C(2)—H Arylation of 3-(2-Aminopyrimidin-4-yl)indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3945-3959.
[12]	Jiling Yi, Kangqi Shi, Binglin Wu, Wanshan Li, Guangying Chen. Study on Secondary Metabolites of Marine-Derived Fungus Eutypella sp. F0219 [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 295-298.
[13]	Panpan Lei, Qinlin Chen, Hang Chen, Yang Zhou, Linhai Jin, Wei Wang, Fener Chen. Synthesis of Bibenzyl Derivatives via Visible-Light-Promoted 1,5-Hydrogen Atom Transfer/Radical Coupling Reactions of N-Fluorocarboxamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 254-264.
[14]	Guangping Liang, Wei Wang, Xuxiu Zhu, Guangyan Liang, Jun Yang, Daoping Wang. Synthesis and in Vitro Anti-tumor Activity of Novel Spliced Compounds of Zidovudine and 4-Anilinoquinazolines [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2793-2805.
[15]	Rong Zhang, Xiang Gao, Lingling Chen, Fajun Nan. Discovery and Structure-Activity Relationship Studies of Thiazole- Oxazole Tandem Heterocyclic RNA Splicing Inhibitors [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2925-2939.