Design and synthesis of hydrazine and oxadiazole-containing derivatives of Sorafenib as antitumor agents

Yuan-you Wang , Jian-zhen Liu , Xiao-yue Yu , De-zhi Yang , Lin-na Zhang , Gui-sen Zhao

Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (3) : 454 -459.

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Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (3) : 454 -459. DOI: 10.1007/s40242-013-2490-3
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Design and synthesis of hydrazine and oxadiazole-containing derivatives of Sorafenib as antitumor agents

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Abstract

A series of hydrazine and oxadiazole analogs of Sorafenib was designed, synthesized and characterized by proton nuclear magnetic resonance(1H NMR) spectrometry and high resolution mass spectrometry(HRMS). The antiproliferative activities of these compounds against human colorectal carcinoma(HCT-116) and human breast cancer (MDA-MB-231) tumor cell lines were evaluated in vitro by MTT method[MTT=3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide]. The bioassay results suggest that most of the synthesized compounds have antitumor potential to HCT-116 cell line compared with MDA-MB-231 cell line. Compounds 8a, 8b, 8d, 8e, 9f and 9j competitive with Sorafenib demonstrated antiproliferative activities on HCT-116 cell line.

Keywords

Sorafenib analog / Antiproliferative activity / Antitumor agent

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Yuan-you Wang, Jian-zhen Liu, Xiao-yue Yu, De-zhi Yang, Lin-na Zhang, Gui-sen Zhao. Design and synthesis of hydrazine and oxadiazole-containing derivatives of Sorafenib as antitumor agents. Chemical Research in Chinese Universities, 2013, 29(3): 454-459 DOI:10.1007/s40242-013-2490-3

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References

[1]

Smalley K S, Haass N K, Brafford P A, Lioni M, Flaherty K T, Herlyn M. Mol. Cancer Ther., 2006, 5: 1136.

[2]

Sergina N V, Rausch M, Wang D, Blair J, Hann B, Shokat K M, Moasser M M. Nature, 2007, 445: 437.

[3]

Balz L M, Bartkowiak K, Andreas A, Pantel K, Niggemann B, Zanker K S, Brandt B H, Dittmar T. J. Pathol., 2012, 227: 234.

[4]

Vazquez S, Leon L, Fernandez O, Lazaro M, Grande E, Aparicio L. Adv. Ther., 2012, 29: 202.

[5]

Gild M L, Bullock M, Robinson B G, Clifton-Bligh R. Nat. Rev. Endocrinol., 2011, 7: 617.

[6]

Ranieri G, Gadaleta-Caldarola G, Goffredo V, Patruno R, Mangia A, Rizzo A, Sciorsci R L, Gadaleta C D. Curr. Med. Chem., 2012, 19: 938.

[7]

Yao J, Chen J, He Z, Sun W, Xu W. Bioorg. Med. Chem., 2012, 20: 2923.

[8]

Sun M, Wu X, Chen J, Cai J, Cao M, Ji M. Eur. J. Med. Chem., 2010, 45: 2299.

[9]

Kumar D, Patel G, Chavers A K, Chang K H, Shah K. Eur. J. Med. Chem., 2011, 46: 3085.

[10]

Boström J, Hogner A, Llinàs A, Wellner E, Plowright A T. J. Med. Chem., 2012, 55: 1817.

[11]

Singh N K, Singh N, Prasad G C, Sodhi A, Shrivastava A. Bioorg. Med. Chem., 1997, 5: 245.

[12]

Mohareb R M, Fleita D H, Sakka O K. Molecules, 2011, 16: 16.

[13]

Wilhelm S M, Carter C, Tang L, Wilkie D, McNabola A, Rong H, Chen C, Zhang X, Vincent P, McHugh M, Cao Y, ShuJath J, Gawlak S, Eveleigh D, Rowley B, Liu L, Adnane L, Lynch M, Auclair D, Taylor I, Gedrich R, Voznesensky A, Riedl B, Post L E, Bollag G, Trail P A. Cancer Res., 2004, 64: 7099.

[14]

Dydio P, Zieliński T, Jurczak J. J. Org. Chem., 2009, 74: 1525.

[15]

Rajapakse H A, Zhu H, Young M B, Mott B T. Tetrahedron Lett., 2006, 47: 4827.

[16]

Liu P, Zhang J, Yan T, Xiong L, Li Z. Chem. Res. Chinese Universities, 2012, 28(3): 430.

[17]

Riedl B, Dumas J, Khire U, Lowinger T B, Scott W L, Smith R A, Wood J E, Monahan M K, Natero R, Renick J, Sibley R N. Omega-Carboxyaryl Substituted Diphenyl Ureas as Raf Kinase Inhibitiors, US7235576 B1, 2007.

[18]

Deegan T L, Nitz T J, Cebzanov D, Pufko D E, Porco J A. Bioorg. Med. Chem. Lett., 1999, 9: 209.

[19]

Hu G, Wang G, Duan N, Wen X, Cao T, Xie S, Huang W. Chem. Res. Chinese Universities, 2012, 28(6): 980.

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