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

Abdul Manan, Mohd Abdul Fatah and Crouse, Karen Anne and Mohamed Tahir, Mohamed Ibrahim and Rosli, Rozita and How, Fiona Ni Foong and Watkins, David J. and Slawin, Alexandra Martha Zoya (2011) Synthesis, characterization and cytotoxic activity of S-benzyldithiocarbazate Schiff bases derived from 5-fluoroisatin, 5-chloroisatin, 5-bromoisatin and their crystal structures. Journal of Chemical Crystallography, 41 (12). pp. 1630-1641. ISSN 1074-1542

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Abstract

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 lM (2.6 lg/mL) and 9.26 lM (3.2 lg/mL) respectively while the chloride derivative was weakly active with an IC50 value of 38.69 lM (14.0 lg/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.

Item Type:	Article (Journal)
Additional Information:	6467/7866
Uncontrolled Keywords:	Dithiocarbazate, Schiff base, Isatin, MCF-7, Structure
Subjects:	Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Science Kulliyyah of Science > Department of Biotechnology
Depositing User:	Dr Fiona How
Date Deposited:	24 Nov 2011 13:21
Last Modified:	21 Jun 2013 09:26
URI:	http://irep.iium.edu.my/id/eprint/7866

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