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

• Main Authors: Abdul Manan, Mohd Abdul Fatah, Crouse, Karen Anne, Mohamed Tahir, Mohamed Ibrahim, Rosli, Rozita, How, Fiona Ni Foong, Watkin, David J., Slawin, Alexandra M. Z.
• Format: Article
• Language: English
• Published: Springer 2011
• Online Access: http://psasir.upm.edu.my/id/eprint/24968/1/24968.pdf; http://psasir.upm.edu.my/id/eprint/24968/
• Institution: Universiti Putra Malaysia

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.