Abstract
A series of novel Schiff bases including 4-tert-butyl-5-benzyl-2-benzyliminothiazoles was synthesized by reacting the aromatic aldehydes with the corresponding 2-aminothiazoles. The antitumor bioassay revealed that compounds 2n and 2m exhibited potent cytotoxicity against human cervix cancer(HeLa) cell line with IC50 values of 0.001 and 0.007 mmol/L, respectively. The preliminary structure-activity relationship(SAR) investigations and the apoptosis evaluation suggest that 4-tert-butyl-5-benzyl-2-benzyliminothiazoles may be a satisfactory backbone for antitumor activity, and compound 2n can serve as an attractive candidate for the development of novel apoptosis in anticancer treatment.
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Holla B. S., Malini K.V., Rao B. S., Sarojini B. K., Kumari N. S., Eur. J. Med. Chem., 2003, 38, 313
Li M., Sim Y., Ham S. W., Bull. Korean Chem. Soc., 2010, 31, 1463
Souza M.V. N. D., J. Sulfur Chem., 2005, 26, 429
Gorczynski M. J., Leal R. M., Mooberry S. L., Bushweller J. H., Brown M. L., Bioorg. Med. Chem., 2004, 12, 1029
Misra R. N., Xiao H. Y., Williams D. K., Kim K. S., Lu S. F., Keller K. A., Mulheron J. G., Batorsky R., Tokarski J. S., Sack J. S., Kimball S. D., Lee F. Y., Webster K. R., Bioorg. Med. Chem. Lett., 2004, 14, 2973
Shao L., Zhou X., Jin Z., Fang J. X., Heteroat. Chem., 2008, 19, 2
Steinberg M., Clinical Therapeutics, 2007, 29, 2289
Lombardo L. J., Lee F. Y., Chen P., Norris D., Barrish J. C., Behnia K., Castaneda S., Cornelius L. A. M., Das J., Doweyko A. M., Fairchild C., Hunt J. T., Inigo I., Johnston K., Kamath A., Kan D., Klei H., Marathe P., Pang S., Peterson R., Pitt S., Schieven G. L., Schmidt R. J., Tokarski J., Wen M. L., Wityak J., Borzilleri R. M., J. Med. Chem., 2004, 47, 6658
Walsby E., Lazenby M., Pepper C., Burnett A. K., Leukemia, 2011, 25, 411
Özkay Y., İncesu Z., Işıkdağ İ., Yeşilkaya M., Cell Biochem. Funct., 2008, 26, 102
Wang P. H., Keck J. G., Lien E. J., Lai M. M. C., J. Med. Chem., 1990, 33, 608
Tang A., Lien E. J., Lai M. M. C., J. Med. Chem., 1985, 28, 1103
Zhou X., Shao L., Jin Z., Liu J. B., Dai H., Fang J. X., Heteroat. Chem., 2007, 18, 55
Hu A. X., Qin Z., Chen P., Ye J., Chin. J. Org. Chem., 2010, 30, 923
Yang L. T., Qin Z., Chen P., Hu A. X., Chin. J. Appl. Chem., 2010, 27, 664
Hu A. X., Xu J. P., Lin H. B., Ye J., The Synthesis and Application of Thiazole Schiff Bases with Nitro-group, CN 101492426, 2009-7-29
Hu A. X., Cao G., Ma Y. Q., Zhang J. Y., Ou X. M., Chin. J. Struct. Chem., 2008, 27, 1235
Wang Y., Hu A. X., Cao G., Li G. X., Zhang J. Y., Xia L., Ou X. M., Xu J. B., Chin. J. Org. Chem., 2008, 28, 443
Hu A. X., Cao G., Tetrahedron: Asymmetry, 2011, 22, 1332
Hu A. X., Cao G., Xu J. J., Xia L., He D. H., J. Hunan University, Natural Sciences, 2007, 34, 78
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Supported by the National Science & Technology Pillar Program of China(No.2011BAE06B01) and the Natural Science Foundation of Hunan Province, China(No.12jj3012).
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Ye, J., Qiu, S., Hu, A. et al. Synthesis and antitumor activity of 4-tert-butyl-5-benzyl-2-benzyliminothiazoles. Chem. Res. Chin. Univ. 30, 49–54 (2014). https://doi.org/10.1007/s40242-013-3345-6
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DOI: https://doi.org/10.1007/s40242-013-3345-6