Synthesis, characterization and cytotoxic activity of S- benzyldithiocarbazate Schiff bases derived from 5-fluoroisatin, 5-chloroisatin, 5-bromoisatin and their crystal structures

• Main Authors: Crouse, K.A (Author), How, F.N.-F (Author), Manan, M.A.F.A (Author), Rosli, R. (Author), Slawin, A.M.Z (Author), Tahir, M.I.M (Author), Watkin, D.J (Author)
• Format: Article
• Language: English
• Subjects: Dithiocarbazate; Isatin; MCF-7; Schiff base; Structure
• Online Access: View Fulltext in Publisher; View in Scopus

 Schiff bases were prepared from S-benzyldithiocarbazate with 5-fluro-, 5-chloro- and 5-bromoisatin. All are potential tridentate nitrogen, oxygen, sulfur donors. They were found to be selectively active against MCF-7 cell line (Human non-metastatic mammary gland adenocarcinoma cell line). The bromide and fluoride compounds were the most active with IC50 values of 6.40 μM (2.6 μg/mL) and 9.26 μM (3.2 μg/mL) respectively while the chloride derivative was weakly active with an IC50 value of 38.69 μM (14.0 μg/mL). The cytotoxic activity of the halo substituted isatins against the breast cancer cell lines tested is in the order of Br > F > Cl. Planarity of the isatin ring in the Schiff bases can be arranged in the following order SB5FISA > SB5ClISA > SB5BrISA while the perpendicularity of the benzyl ring towards the dithiocarbazate plane can be ordered as follows, SB5FISA > SB5BrISA > SB5ClISA. © 2011 Springer Science+Business Media, LLC.