Synthesis of New Benzothiazole Derivatives and Evaluation of Cytotoxicity of N-(6-Substitued-1,3-benzothiazol-2-yl)-4-phenyl-1,3-thiazol-2(3H)-imine Compounds

Document Type: Research Paper

Authors

1 Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad

2 Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran

3 Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

4 Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

Abstract

Cyclization of unsymmetrical thioureas affords N-(6-substitued-1,3-benzothiazol-2-yl)-4-phenyl-1,3-thiazol-2(3H)-imine compounds by the reaction of 1-(1,3-benzothiazol-2-yl)thiourea derivatives and 2-bromoacetophenone in the presence of Et3N. Also, methyl-1,3-benzothiazol-2-yl carbamodithioate derivatives with methyl anthranilate were reacted and 3-(benzo[d]thiazol-2-yl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives as new compounds are synthesized. In the following, synthesized compounds (2a- 2d) were evaluated for anti-tumor activity against MCF-7, MAD-MD-231, HT-29, HeLa, Neuro-2a, K-562 and L-929 cell lines and the results obtained from MTT-assay revealed the best cytotoxicity for 2b compound containing a phenolic segment in their buildings. On the other hand, apoptosis assay for this compound was also carried out by flow cytometry supporting the other results.

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