Biological Evaluation and Structure Modification of (S)-3-Aminopyrrolidine Derivatives

doi:10.1007/s40242-014-3174-3

高等学校化学研究 ›› 2014, Vol. 30 ›› Issue (1): 91-97.doi: 10.1007/s40242-014-3174-3

Biological Evaluation and Structure Modification of (S)-3-Aminopyrrolidine Derivatives

XIN Tian^1,2,3, ZHANG Cunlong^2,3, TAN Chunyan^2,3, JIANG Yuyang^1,2,3,4

1. Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China;
2. State Key Laboratory Breeding Base-Shenzhen Key Laboratory of Chemical Biology, Tsinghua University, Shenzhen 518055, P. R. China;
3. Shenzhen Anti-tumor Drug Development Engineering Laboratory, Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, P. R. China;
4. Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084, P. R. China

收稿日期:2013-04-17 修回日期:2013-05-15 出版日期:2014-02-01 发布日期:2013-06-13
通讯作者: TAN Chunyan,E-mail:jiangyy@sz.tsinghua.edu.cn; JIANG Yuyang,E-mail:tancy@sz.tsinghua.edu.cn E-mail:jiangyy@sz.tsinghua.edu.cn; tancy@sz.tsinghua.edu.cn
基金资助:
Supported by the National Science and Technology Major Special Project for New Drug Research and Design of China (No.2012ZX09506001-010) and the National Basic Research Program of China(No.2012CB722605).

Biological Evaluation and Structure Modification of (S)-3-Aminopyrrolidine Derivatives

XIN Tian^1,2,3, ZHANG Cunlong^2,3, TAN Chunyan^2,3, JIANG Yuyang^1,2,3,4

1. Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China;
2. State Key Laboratory Breeding Base-Shenzhen Key Laboratory of Chemical Biology, Tsinghua University, Shenzhen 518055, P. R. China;
3. Shenzhen Anti-tumor Drug Development Engineering Laboratory, Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, P. R. China;
4. Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing 100084, P. R. China

Received:2013-04-17 Revised:2013-05-15 Online:2014-02-01 Published:2013-06-13
Contact: TAN Chunyan,E-mail:jiangyy@sz.tsinghua.edu.cn; JIANG Yuyang,E-mail:tancy@sz.tsinghua.edu.cn E-mail:jiangyy@sz.tsinghua.edu.cn; tancy@sz.tsinghua.edu.cn
Supported by:
Supported by the National Science and Technology Major Special Project for New Drug Research and Design of China (No.2012ZX09506001-010) and the National Basic Research Program of China(No.2012CB722605).

摘要/Abstract

摘要：

With our interest in (S)-3-aminopyrrolidine derivatives, we further screened inhibition activities of three hit compounds on many other kinases with the results demonstrating that this series of compounds shows better anticancer activities, which might result from the main block of PI3K/Akt signaling pathway and the inhibition of Abelson murine leukemia viral oncogene homolog(ABL) kinase, as well as some epidermal growth factors. Further structure modification demonstrates that benzylsulfonyl group is the necessary functional group contributing to the biological activity that will be helpful to guiding us to optimize these (S)-3-aminopyrrolidine derivatives.

关键词: (S)-3-Aminopyrrolidine, Biological evaluation, Structure modification

Abstract:

Key words: (S)-3-Aminopyrrolidine, Biological evaluation, Structure modification

XIN Tian, ZHANG Cunlong, TAN Chunyan, JIANG Yuyang. Biological Evaluation and Structure Modification of (S)-3-Aminopyrrolidine Derivatives[J]. 高等学校化学研究, 2014, 30(1): 91-97.

XIN Tian, ZHANG Cunlong, TAN Chunyan, JIANG Yuyang. Biological Evaluation and Structure Modification of (S)-3-Aminopyrrolidine Derivatives[J]. Chemical Research in Chinese Universities, 2014, 30(1): 91-97.

参考文献

[1] Druker B. J., Talpaz M., Resta D. J., Peng B., Buchdunger E., Ford J. M., Lydon N. B., Kantarjian H., Capdeville R., Ohno-Jones S., Sawyers C. L., N. Engl. J. Med., 2001, 344, 1031

[2] Liao J. J. L., J. Med. Chem., 2007, 50, 409

[3] Morphy R., J. Med. Chem., 2010, 53, 1413

[4] Golas J. M., Arndt K., Etienne C., Lucas J., Nardin D., Gibbons J., Frost P., Ye F., Boschelli D. H., Boschelli F., Cancer Res., 2003, 63, 375

[5] Kimura S., Naito H., Segawa H., Kuroda J., Yuasa T., Sato K., Yokota A., Kamitsuji Y., Kawata E., Ashihara E., Nakaya Y., Naruoka H., Wakayama T., Nasu K., Asaki T., Niwa T., Hirabayashi K., Maekawa T., Blood, 2005, 106, 3948

[6] Lockton J. A., Smethurst D., Macpherson M., Tootell R., Marshall A. L., Clack G., Gallagher N. J., J. Clin. Oncol., 2005, 23, 223s

[7] Daub H., Specht K., Ullrich A., Nat. Rev. Drug Discovery, 2004, 3, 1001

[8] Shah N. P., Nicoll J. M., Nagar B., Gorre M. E., Paquette R. L., Kuriyan J., Sawyers C. L., Cancer Cell, 2002, 2, 117

[9] Weisberg E., Griffin J. D., Drug Resist. Updates, 2001, 4, 22

[10] Weisberg E., Griffin J. D., Blood, 2000, 95, 3498

[11] Engelman J. A., Zejnullahu K., Mitsudomi T., Song Y. C., Hyland C., Park J. O., Lindeman N., Gale C. M., Zhao X. J., Christensen J., Kosaka T., Holmes A. J., Rogers A. M., Cappuzzo F., Mok T., Lee C., Johnson B. E., Cantley L. C., Janne P. A., Science, 2007, 316, 1039

[12] Huo X., Zhang Q., Liu Y., Chem. Res. Chinese Universities, 2010, 26(3), 409

[13] Burchert A., Wang Y., Cai D., Bubnoff N. V., Paschka P., Muller-Brusselbach S., Ottmann O. G., Duyster J., Hochhaus A., Neubauer A., Leukemia, 2005, 19, 1774

[14] Apsel B., Blair J. A., Gonzalez B., Nazif T. M., Feldman M. E., Aizenstein B., Hoffman R., Williams R. L., Shokat K. M., Knight Z. A., Nat. Chem. Biol., 2008, 4, 691

[15] Peng H., Huang N., Qi J., Xie P., Xu C., Wang J. X., Yang C. Z., Bioorg. Med. Chem. Lett., 2003, 13, 3693

[16] Zhang C. L., Tan C. Y., Zu X. Y., Zhai X., Liu F., Chu B. Z., Ma X. H., Chen Y. Z., Gong P., Jiang Y. Y., Eur. J. Med. Chem., 2011, 46, 1404

[17] Yano S., Nishioka Y., Goto H., Sone S., Assay Drug Dev. Technol., 2007, 5, 75

[18] Konecny G. E., Pegram M. D., Venkatesan N., Finn R., Yang G. R., Rahmeh M., Untch M., Rusnak D. W., Spehar G., Mullin R. J., Keith B. R., Gilmer T. M., Berger M., Podratz K. C., Slamon D. J., Cancer Sci., 2003, 94, 479

[19] Liu H. C., Dong A. J., Gao C. M., Tan C. Y., Liu H. X., Zu X. Y., Jiang Y. Y., Cancer Res., 2006, 66, 1630

[20] Baki A., Bielik A., Molnar L., Szendrei G., Keseru G. M., Bioorg. Med. Chem., 2008, 16, 100

Biological Evaluation and Structure Modification of (S)-3-Aminopyrrolidine Derivatives

Biological Evaluation and Structure Modification of (S)-3-Aminopyrrolidine Derivatives

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 6

编辑推荐

Metrics

本文评价

[1]	LONG Bohua, ZHANG Jingzhao, WANG Xueyan, TANG Xudong, WU Zhengzhi. Total Synthesis and Biological Evaluation of Wewakazole[J]. 高等学校化学研究, 2017, 33(6): 890-894.
[2]	WANG Yang, LEI Fan, LI Xiaolong, HE Yi, LI Jue, QIU Rui, WU Xueying, HAI Li, WU Yong. Structure-based Design, Synthesis and Anti-influenza A Virus Activities of Substituted Phenyl-coupled Heterocyclic Ethylamide Derivatives[J]. 高等学校化学研究, 2015, 31(6): 942-951.
[3]	LIAO Huimin, CHONG Lian'e, TAN Li, CHEN Xiaodan, YOU Rui, GONG Ping. Synthesis and Biological Evaluation of Novel 5,7-Diphenylimidazo[1,2-a]pyridine Derivatives[J]. 高等学校化学研究, 2014, 30(5): 759-763.
[4]	PARVEEN Mehtab, MALLA Ali Mohammed, ALI Akhtar, ALAM Mahboob, MUSTAFA Mir Faisal. Silica-supported Thionyl Chloride-assisted Synthesis and Bioassay of Novel Tetrazinan-3-thione and 3-Oxo-pyrazolidine-4-carbonitrile Derivatives of Steroids[J]. 高等学校化学研究, 2014, 30(1): 55-62.
[5]	LIU Zhi-hui, LI De-jun, JIANG Dan, XIAO Chuan, SONG Zhi-guang, JIN Ying-hua. Design, Synthesis and Antitumor Activity in vitro of a Series of 3-Arylcoumarins[J]. 高等学校化学研究, 2013, 29(6): 1125-1128.
[6]	MENG Yan-qiu, DING Jia-qi, LIU Yuan, NIE Hui-hui, GUAN Sai, ZOU Chao, ZHAO Na, CHEN Hong, CAO Bo. Synthesis and Anti-tumor Activity of Novel Glycyrrhetinic Acid Derivatives[J]. 高等学校化学研究, 2012, 28(2): 214-219 .