Chinese Journal of Organic Chemistry >
Synthesis and Antitumor Evaluation of 3-epi-Jaspine B Analogues
Received date: 2016-07-19
Revised date: 2016-08-19
Online published: 2016-09-08
Supported by
Project supported by the National Natural Science Foundation of China(No. U1204206) and the Education Department of Henan Province(No. 17A350004).
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.
Key words: 3-epi-jaspine B; antitumor; hydrogen sulfide; analogue
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
[1] Kuroda, I.; Musman, M.; Ohtani, Ⅱ; Ichiba, T.; Tanaka, J.; Gravalos, D. G.; Higa, T. J. Nat. Prod. 2002, 65, 1505.
[2] Ledroit, V.; Debitus, C.; Lavaud, C.; Massiot, G. Tetrahedron Lett. 2003, 44, 225.
[3] Liu, J.; Du, Y.; Dong, X.; Meng, S.; Xiao, J.; Cheng, L. Carbo-hydr. Res. 2006, 341, 2653.
[4] Salma, Y.; Lafont, E.; Therville, N.; Carpentier, S.; Bonnafe, M.-J.; Levade, T.; Genisson, Y.; Andrieu-Abadie, N. Biochem. Pharmacol. 2009, 78, 477.
[5] Yoshimitsu, Y.; Oishi, S.; Miyagaki, J.; Inuki, S.; Ohno, H.; Fujii, N. Bioorg. Med. Chem. 2011, 19, 5402.
[6] Inuki, S.; Yoshimitsu, Y.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2010, 75, 3831.
[7] Passiniemi, M.; Koskinen, A. M. P. Org. Biomol. Chem. 2011, 9, 1774.
[8] Llaveria, J.; Diaz, Y.; Matheu, M. I.; Castillon, S. Eur. J. Org. Chem. 2011, 8, 1514.
[9] Salma, Y.; Ballereau, S.; Ladeira, S.; Lepetit, C.; Chauvin, R.; Andrieu-Abadie, N.; Genisson, Y. Tetrahedron 2011, 67, 4253.
[10] Jeon, H.; Bae, H.; Baek, D. J.; Kwak, Y.-S.; Kim, D.; Kim, S. Org. Biomol. Chem. 2011, 9, 7237.
[11] Santos, C.; Fabing, I.; Saffon, N.; Ballereau, S.; Genisson, Y. Tetrahedron 2013, 69, 7227.
[12] Kundooru, S.; Das, P.; Meena, S.; Kumar, V.; Siddiqi, M. I.; Datta, D.; Shaw, A. K. Org. Biomol. Chem. 2015, 13, 8241.
[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.
[14] Martinkova, M.; Mezeiova, E.; Fabisikova, M.; Gonda, J.; Pilatova, M.; Mojzis, J. Carbohydr. Res. 2015, 402, 6.
[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.
[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.
[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.
[18] McRobb, F. M.; Crosby, I. T.; Yuriev, E.; Lane, J. R.; Capuano, B. J. Med. Chem. 2012, 55, 1622.
[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.
[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.
[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.
[22] Shen, Y.; Shen, Z.; Luo, S.; Guo, W.; Zhu, Y. Z. Oxid. Med. Cell. Longevity 2015, 2015.
[23] Kodela, R.; Chattopadhyay, M.; Kashfi, K. ACS Med. Chem. Lett. 2012, 3, 257.
[24] Zhao, M.-L.; Zhang, E.; Gao, J.; Zhang, Z.; Zhao, Y.-T.; Qu, W.; Liu, H.-M. Carbohydr. Res. 2012, 351, 126.
[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.
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