Notes

Synthesis and Anti-tumor Activity Evaluation of Alkyl Heterocyclyl Disulfides

  • Gong Jingxu ,
  • Sheng Li ,
  • Yao Ligong ,
  • Li Jia ,
  • Zhou Yubo ,
  • Guo Yuewei
Expand
  • State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received date: 2011-01-20

  Revised date: 2011-11-08

  Online published: 2012-03-24

Supported by

Project supported by the National S & T Major Project (Nos. 2009ZX09301-001, 2009ZX09103-060), the Natural Science Foundation of China (Nos. 81072572, 21072204, 21021063), the National Marine “863” Project (No. 2011AA09070102), the Basic Research Project of Shanghai Science and Technology Commission (Nos. 09ZR1438000, 10540702900), and the Key Program of the Chinese Academy of Sciences (Nos. KSCX2-EW-R-15, KSCX2-YW-R-18).

Abstract

A series of alkyl heterocyclyl disulfides were prepared by reaction of the heterocyclyl thiol with Bunte salts. All the synthesized compounds showed interesting inhibit activities toward human colon carcinoma cells (HCT-116) in vitro. The IC50 values of the tested compounds ranged from 4.8 μg·mL-1 to 17.7 μg·mL-1.

Cite this article

Gong Jingxu , Sheng Li , Yao Ligong , Li Jia , Zhou Yubo , Guo Yuewei . Synthesis and Anti-tumor Activity Evaluation of Alkyl Heterocyclyl Disulfides[J]. Chinese Journal of Organic Chemistry, 2012 , (03) : 593 -596 . DOI: 10.6023/cjoc1101201

References

[1] Park, H. B.; Kwon, H. C.; Lee, C.-H.; Yang, H. O. J. Nat. Prod.2009, 72, 248.  

[2] Turos, E.; Revell, K. D.; Ramaraju, P.; Gergeres, D. A.;Greenhalgh, K.; Young, A.; Sathyanarayan, N.; Dickey, S.; Lim, D.;Alhamadsheh, M. M.; Reynolds, K. Bioorg. Med. Chem. 2008, 16,6501.  

[3] (a) Hunter, R.; Kaschula, C. H.; Parker, I. M.; Caira, M. R.;Richards, P.; Travis, S.; Taute, F.; Qwebani, T. Bioorg. Med. Chem.Lett. 2008, 18, 5277.(b) O'Donnell, G.; Poeschl, R.; Zimhony, O.; Gunaratnam, M.;Moreira, J. B. C.; Neidle, S.; Evangelopoulos, D.; Bhakta, S.;Malkinson, J. P.; Boshoff, H. I.; Lenaerts, A.; Gibbons, S. J. Nat.Prod. 2009, 72, 360.(c) Ryu, E. K.; Choe, Y. S.; Byun, S. S.; Lee, K.-H.; Chi, D. Y.;Choi, Y.; Kim, B.-T. Bioorg. Med. Chem. 2004, 12, 859.  

[4] Cesarini, S.; Spallarossa, A.; Ranise, A.; Schenone, S.; Bruno, O.; PColla, L.; Casula, L.; Collu, G.; Sanna, G.; Loddo, R. Bioorg. Med.Chem. 2008, 16, 6353.  

[5] Cragg, G. M.; Grothaus, P. G.; Newman, D. J. Chem. Rev. 2009,109, 3012.  

[6] Sun, Y.-Q.; Guo, Y.-W. Tetrahedron Lett. 2004, 45, 5533.  

[7] Liu H.-L.; Shen, X.; Jiang, H.; Guo, Y.-W. Chin. J. Org. Chem.2008, 28, 246 (in Chinese).(刘海利, 沈旭, 蒋华良, 郭跃伟, 有机化学, 2008, 28, 246.)

[8] Gong, J.-X.; Shen, X.; Yao, L.-G.; Jiang, H.-L.; Krohn, K.; Guo,Y.-W. Org. Lett. 2007, 9, 1715.

[9] Gong, J.-X.; Sun, Y.-Q.; Wang, J.-D.; Guo, Y.-W. Chin. J. Org.Chem. 2008, 28, 246 (in Chinese).(龚景旭, 孙燕秋, 王继栋, 郭跃伟, 有机化学, 2008, 28, 252.)

[10] Perrin, D. D.; Armarego, W.L. F.; Perrin, D. R. Purification ofLaboratory Chemicals, Pergamon Press, Oxford, 1980.

[11] Zhang, J.; Yang, S.; Liu, W.; Xue, Q. Tribol. Lett. 1999, 7, 173.  

[12] Tanaka, K.; Ajiki, K. Tetrahedron Lett. 2004, 45, 5677.  

[13] Ozelli, R. N.; Scheer, H. DE 2456900, 1976 [Chem. Abstr. 1976,85, 125527].

[14] Xue, Q.; Zhang, J.; Liu, W.; Yang, S. Tribol. Lett. 1999, 7, 27.  

[15] Kirkpatrick, D. L. US 6552060, 2003 [Chem. Abstr. 2003, 138,314629].

[16] Kikrpatrick, D. L.; Jimale, M. L.; King, K. M.; Chen, T. Eur. J.Med. Chem. 1992, 27, 33.

[17] Jayasuriya, N.; Regen, S. Tetrahedron Lett. 1992, 33, 451.  

[18] Stellenboom, N.; Hunter, R.; Caira, M. R. Tetrahedron 2010, 66,3228.  

[19] Hiver, P.; Dicko, A.; Paquer, D. Tetrahedron Lett. 1994, 35, 9569.  

[20] Hunter, R.; Caira, M.; Stellenboom, N. J. Org. Chem. 2006, 71,8268.  

[21] Tanaka, K.; Ajiki, K. Tetrahedron Lett. 2004, 45, 5677.  

[22] Sirakawa, K.; Aki, O.; Tsujikawa, T.; Tsuda, T. Chem. Pharm.Bull. 1970, 18, 235.  
Outlines

/