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

• Published in: Journal of Chemical Crystallography
• Main Author: Manan M.A.F.A.; Crouse K.A.; Tahir M.I.M.; Rosli R.; How F.N.-F.; Watkin D.J.; Slawin A.M.Z.
• Format: Article
• Language: English
• Published: 2011
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-80054986130&doi=10.1007%2fs10870-011-0151-2&partnerID=40&md5=458f71b1e30ef80e104304736cbb6d71

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.