Citation: Zhang En, Wang Shang, Jiao Weiwei, Wang Mingming, Yue Jingfei, Xu Shuaimin, Wang Ya'na, Ambrosi Horst-Dieter, Liu Hongmin. Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 141-148. doi: 10.6023/cjoc201607028 shu

Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues

a.
Collaborative Innovation Center of New Drug Research and Saftry Evaluation, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001
b.
AnalytiCon Discovery GmbH, Hermannswerder Haus 17, 14473 Potsdam, Germany

Corresponding author: Zhang En, zhangen@zzu.edu.cn Wang Ya'na, wangyn@zzu.edu.cn
Received Date: 19 July 2016
Revised Date: 19 August 2016

Fund Project: the National Natural Science Foundation of China U1204206the Education Department of Henan Province 17A350004

Figures(3)

Jaspine B is a natural product with significant antitumor activity, which was isolated from the marine sponge Pachastrissa sp.In order to find new antitumor compounds with high efficiency and succinct synthetic methods, a series of 3-epi-jaspine B analogues were designed and synthesized.16 compounds were synthesized and all of them were unknown in the literature.Their structures were determined by ¹H NMR, ¹³C NMR and HRMS.The antitumor activity of these compounds against four tumor cell lines B16-F10, A-549, MCF-7 and PC-3 was assayed using thiazolyl blue (MTT) assay, and some compounds showed potent inhibitory effect on tumor cells.Compounds 8f and 11 were more potent against A-549 with IC₅₀ of (9.646±0.984) and (7.144±0.854)μg/mL.
- 3-epi-jaspine B,
- antitumor,
- hydrogen sulfide,
- analogue
1. [1]
  Kuroda, I.; Musman, M.; Ohtani, Ⅱ; Ichiba, T.; Tanaka, J.; Gravalos, D. G.; Higa, T. J. Nat. Prod. 2002, 65, 1505. doi: 10.1021/np010659y
2. [2]
  Ledroit, V.; Debitus, C.; Lavaud, C.; Massiot, G. Tetrahedron Lett. 2003, 44, 225. doi: 10.1016/S0040-4039(02)02541-8
3. [3]
  Liu, J.; Du, Y.; Dong, X.; Meng, S.; Xiao, J.; Cheng, L. Carbo-hydr. Res. 2006, 341, 2653. doi: 10.1016/j.carres.2006.08.011
4. [4]
  Salma, Y.; Lafont, E.; Therville, N.; Carpentier, S.; Bonnafe, M.-J.; Levade, T.; Genisson, Y.; Andrieu-Abadie, N. Biochem. Pharmacol. 2009, 78, 477. doi: 10.1016/j.bcp.2009.05.002
5. [5]
  Yoshimitsu, Y.; Oishi, S.; Miyagaki, J.; Inuki, S.; Ohno, H.; Fujii, N. Bioorg. Med. Chem. 2011, 19, 5402. doi: 10.1016/j.bmc.2011.07.061
6. [6]
  Inuki, S.; Yoshimitsu, Y.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2010, 75, 3831. doi: 10.1021/jo100544v
7. [7]
  Passiniemi, M.; Koskinen, A. M. P. Org. Biomol. Chem. 2011, 9, 1774. doi: 10.1039/c0ob00643b
8. [8]
  Llaveria, J.; Diaz, Y.; Matheu, M. I.; Castillon, S. Eur. J. Org. Chem. 2011, 8, 1514.
9. [9]
  Salma, Y.; Ballereau, S.; Ladeira, S.; Lepetit, C.; Chauvin, R.; Andrieu-Abadie, N.; Genisson, Y. Tetrahedron 2011, 67, 4253. doi: 10.1016/j.tet.2011.04.027
10. [10]
  Jeon, H.; Bae, H.; Baek, D. J.; Kwak, Y.-S.; Kim, D.; Kim, S. Org. Biomol. Chem. 2011, 9, 7237. doi: 10.1039/c1ob05920c
11. [11]
  Santos, C.; Fabing, I.; Saffon, N.; Ballereau, S.; Genisson, Y. Tetrahedron 2013, 69, 7227. doi: 10.1016/j.tet.2013.06.091
12. [12]
  Kundooru, S.; Das, P.; Meena, S.; Kumar, V.; Siddiqi, M. I.; Datta, D.; Shaw, A. K. Org. Biomol. Chem. 2015, 13, 8241. doi: 10.1039/C5OB01123J
13. [13]
  Kwon, Y.; Song, J.; Bae, H.; Kim, W.-J.; Lee, J.-Y.; Han, G.-H.; Lee, S. K.; Kim, S. Mar. Drugs 2015, 13, 824. doi: 10.3390/md13020824
14. [14]
  Martinkova, M.; Mezeiova, E.; Fabisikova, M.; Gonda, J.; Pilatova, M.; Mojzis, J. Carbohydr. Res. 2015, 402, 6. doi: 10.1016/j.carres.2014.11.004
15. [15]
  Frydman, B.; Blokhin, A. V.; Brummel, S.; Wilding, G.; Maxuitenko, Y.; Sarkar, A.; Bhattacharya, S.; Church, D.; Reddy, V. K.; Kink, J. A. J. Med. Chem. 2003, 46, 4586. doi: 10.1021/jm030175u
16. [16]
  Foroumadi, A.; Emami, S.; Mansouri, S.; Javidnia, A.; Sae-id-Adeli, N.; Shirazi, F. H.; Shafiee, A. Eur. J. Med. Chem. 2007, 42, 985. doi: 10.1016/j.ejmech.2006.12.034
17. [17]
  Bennett, F.; Saksena, A. K.; Lovey, R. G.; Liu, Y.-T.; Patel, N. M.; Pinto, P.; Pike, R.; Jao, E.; Girijavallabhan, V. M.; Ganguly, A. K. Bioorg. Med. Chem. Lett. 2006, 16, 186. doi: 10.1016/j.bmcl.2005.09.031
18. [18]
  McRobb, F. M.; Crosby, I. T.; Yuriev, E.; Lane, J. R.; Capuano, B. J. Med. Chem. 2012, 55, 1622. doi: 10.1021/jm201420s
19. [19]
  Anandan, S.-K.; Ward, J. S.; Brokx, R. D.; Denny, T.; Bray, M. R.; Patel, D. V.; Xiao, X.-Y. Bioorg. Med. Chem. Lett. 2007, 17, 5995. doi: 10.1016/j.bmcl.2007.07.050
20. [20]
  Finlay, M. R. V.; Acton, D. G.; Andrews, D. M.; Barker, A. J.; Dennis, M.; Fisher, E.; Graham, M. A.; Green, C. P.; Heaton, D. W.; Karoutchi, G. Bioorg. Med. Chem. Lett. 2008, 18, 4442. doi: 10.1016/j.bmcl.2008.06.027
21. [21]
  Lu, M.; Liu, Y.-H.; Goh, H. S.; Wang, J. J. X.; Yong, Q.-C.; Wang, R.; Bian, J.-S. J. Am. Soc. Nephrol. 2010, 21, 993. doi: 10.1681/ASN.2009090949
22. [22]
  Shen, Y.; Shen, Z.; Luo, S.; Guo, W.; Zhu, Y. Z. Oxid. Med. Cell. Longevity 2015, 2015.
23. [23]
  Kodela, R.; Chattopadhyay, M.; Kashfi, K. ACS Med. Chem. Lett. 2012, 3, 257. doi: 10.1021/ml300002m
24. [24]
  Zhao, M.-L.; Zhang, E.; Gao, J.; Zhang, Z.; Zhao, Y.-T.; Qu, W.; Liu, H.-M. Carbohydr. Res. 2012, 351, 126. doi: 10.1016/j.carres.2012.01.013
25. [25]
  Xu, J.-M.; Zhang, E.; Shi, X.-J.; Wang, Y.-C.; Yu, B.; Jiao, W.-W.; Guo, Y.-Z.; Liu, H.-M. Eur. J. Med. Chem. 2014, 80, 593. doi: 10.1016/j.ejmech.2014.03.022
1. [1]
  Xingyu Liao , Xiangming Yi , Kin Shing Chan . 追凶之路上的怪客——硫化氢. University Chemistry, 2025, 40(6): 172-176. doi: 10.12461/PKU.DXHX202408039
2. [2]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
3. [3]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
4. [4]
  Fa Wang , Yu Chen , Hui Chao . Ruthenium(II) Complexes as Photoactivated Chemo-Prodrugs for Hypoxic Tumor Therapy. University Chemistry, 2025, 40(7): 200-212. doi: 10.12461/PKU.DXHX202410024
5. [5]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
6. [6]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
7. [7]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . 高效靶向示踪钙钛矿纳米系统光电增效抗肿瘤. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-. doi: 10.1016/j.actphy.2024.100042
8. [8]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
9. [9]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
10. [10]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
11. [11]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
12. [12]
  Zhicheng JU , Wenxuan FU , Baoyan WANG , Ao LUO , Jiangmin JIANG , Yueli SHI , Yongli CUI . MOF-derived nickel-cobalt bimetallic sulfide microspheres coated by carbon: Preparation and long cycling performance for sodium storage. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 661-674. doi: 10.11862/CJIC.20240363
13. [13]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
14. [14]
  Tingting XU , Wenjing ZHANG , Yongbo SONG . Research advances of atomic precision coinage metal nanoclusters in tumor therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2275-2285. doi: 10.11862/CJIC.20240229
15. [15]
  Jiahui CHEN , Tingting ZHENG , Xiuyun ZHANG , Wei LÜ . Research progress of near-infrared absorption inorganic nanomaterials in photothermal and photodynamic therapy of tumors. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2396-2414. doi: 10.11862/CJIC.20240106
16. [16]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
17. [17]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
18. [18]
  Yuan CONG , Yunhao WANG , Wanping LI , Zhicheng ZHANG , Shuo LIU , Huiyuan GUO , Hongyu YUAN , Zhiping ZHOU . Construction and photocatalytic properties toward rhodamine B of CdS/Fe₃O₄ heterojunction. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2241-2249. doi: 10.11862/CJIC.20240219
19. [19]
  Qinwen Zheng , Xin Liu , Lintao Tian , Yi Zhou , Libing Liao , Guocheng Lv . Mechanism of Fenton catalytic degradation of Rhodamine B induced by microwave and Fe₃O₄. Chinese Chemical Letters, 2025, 36(4): 109771-. doi: 10.1016/j.cclet.2024.109771
20. [20]
  Peng GENG , Guangcan XIANG , Wen ZHANG , Haichuang LAN , Shuzhang XIAO . Hollow copper sulfide loaded protoporphyrin for photothermal-sonodynamic therapy of cancer cells. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1903-1910. doi: 10.11862/CJIC.20240155

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(666)
HTML views(51)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142