Citation: Xu Haiwei, Jia Shilong, Xie Xiaoping, Luo Jiao, Wang Shu. Design, Synthesis and Anti-proliferative Activity of Novel 5, 6-Dihydro-6-alkyl-2-pyrone Analogues[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 902-907. doi: 10.6023/cjoc201612007 shu

Design, Synthesis and Anti-proliferative Activity of Novel 5, 6-Dihydro-6-alkyl-2-pyrone Analogues

Xu Haiwei ^b,*,, ,
Jia Shilong ^a,b ,
Xie Xiaoping ^b ,
Luo Jiao ^b ,
Wang Shu ^a,*,,

a.
Department of Pharmacy, Hebei North University, Zhangjiakou 075000
b.
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001

Corresponding author: Xu Haiwei, xhwei01@126.com Wang Shu, xhwei01@126.com
Received Date: 2 December 2016
Revised Date: 30 December 2016

Fund Project: the Program for Science & Technology Innovation Talents of Henan Province 14HASTIT0031

Figures(2)

In order to investigate whether the modification at the double bonds in the pyrone skeleton would affect their biological activity. Based on the 5, 6-dihydro-6-alkyl-2-pyrone goniothalamin, a series of new compounds 5, 6 and 8 were designed and synthesized, which were obtained by modification at the unsubstituted double bonds. Their cell proliferation inhibition activities against human liver cancer (7721), human lung cancer (A549), human esophageal cancer (EC-109), human gastric cancer (MGC-803) cell lines were assessed by thiazolyl blue tetrazolium bromide (MTT) method. Most of synthetic compounds lost their bioactivities via a comparision with positive control but 6-(benzyloxy) methyl-3-methyl-4-(2, 3, 4, 5-tetra-fluorobenzamine)-5, 6-dihydro-2H-pyran-2-one (6d). The results indicate that the unsaturated double bond is a key functional group for the bioactivity of these compounds and it is possible to keep their anti-cancer proliferation activity and reduce their toxicity by modification of the unsaturated double bond in 5, 6-dihydro-6-alkyl-2-pyrones.
- α, β-unsaturated δ-lactone,
- synthesis,
- cancer,
- antiproliferative activity
1. [1]
  Jong, R.; Mulder, N.; Uges, D. Brit. J. Cancer. 1999, 79, 882. doi: 10.1038/sj.bjc.6690141
2. [2]
  Barros, M. E.; Freitas, J. C.; Oliveira, J. M. Eur. J. Med. Chem. 2014, 76, 291. doi: 10.1016/j.ejmech.2014.02.013
3. [3]
  Seyed, M. A.; Jantan, I.; Bukhari, S. N. A. BioMed Res. Int. 2014, 2014, 536508.
4. [4]
  Sun, Q. X.; Carrasco, Y. P.; Hu, Y. C. P. Natl. Acad. Sci. U. S. A. 2013, 110, 1303. doi: 10.1073/pnas.1217203110
5. [5]
  Sandra, T. G.; Concepcion, V.; Santiago, D. O. Arch. Pharm. Chem. Life Sci. 2015, 348, 541. doi: 10.1002/ardp.v348.8
6. [6]
  Raju, A.; Reddy, A. Y.; Sabitha, G. Tetrahedron Lett. 2015, 56, 5474. doi: 10.1016/j.tetlet.2015.08.029
7. [7]
  Luiz, F. T. N.; Carolina, M. A.; Karin, J. P. R. Chem. Med. Chem. 2015, 10, 1687. doi: 10.1002/cmdc.201500246
8. [8]
  Vilanova, C.; Diaz-Oltra, S.; Murga, J. J. Med. Chem. 2014, 57, 10391. doi: 10.1021/jm501112q
9. [9]
  Marucci, C.; Christodoulou, M. S.; Pieraccini, S. Eur. J. Org. Chem. 2016, 11, 2029.
10. [10]
  Benedekovic, G.; Kovacevic, I.; Popsavin, M. Bioorg. Med. Chem. Lett. 2016, 26, 3318. doi: 10.1016/j.bmcl.2016.05.044
11. [11]
  Li, X. C.; Guo, Z. Y.; Deng, Z. S. Rec. Nat. Prod. 2015, 9, 503.
12. [12]
  He, H. Y.; Ratnayake, A. S.; Janso, J. E. J. Nat. Prod. 2014, 77, 1864. doi: 10.1021/np500342m
13. [13]
  Marco, J. A.; García-Pla, J.; Carda, M. Eur. J. Med. Chem. 2011, 46, 1630. doi: 10.1016/j.ejmech.2011.02.011
14. [14]
  Kim, J. H.; Lee, S. J.; Org. Lett. 2011, 13, 1350. doi: 10.1021/ol200045q
15. [15]
  Kim, J. H.; Shin, H.; Lee, S. G. J. Org. Chem. 2012, 77, 1560. doi: 10.1021/jo201964a
16. [16]
  Cao, X. F.; Sun, T. T.; Ke, S. Y. Chin. J. Org. Chem. 2010, 30, 1113 (in Chinese).
17. [17]
  Koziol, A.; Lendzion-Paluch, A.; Manikowski, A. Org. Proc. Res. Dev. 2013, 17, 869. doi: 10.1021/op300367c
18. [18]
  Zhao, J. Y.; Zheng, Z. H.; Huang, Q. F.; Deng, J. G.; Zhu, J.; Wang, Q. W. Chin. J. Org. Chem. 2016, 36, 648 (in Chinese).
19. [19]
  Pospisil, J.; Marko, I. E. J. Am. Chem. Soc. 2007, 129, 3516. doi: 10.1021/ja0691728
20. [20]
  Ramesh, D.; Rajaram, S.; Peddikotla, P. Helv. Chim. Acta 2011, 94, 1226. doi: 10.1002/hlca.v94.7
21. [21]
  AnkiReddy, S.; AnkiReddy, P.; Sabitha, G. Org. Biomol. Chem. 2015, 13, 10487. doi: 10.1039/C5OB01598G
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