Synthesis,Characterization and Cytotoxic Activity of S-Benzyldithiocarbazate Schiff Bases Derived from 5-Fluoroisatin, 5-Chloroisatin, 5-Bromoisatin and Their Crystal Structures |
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| Authors: | Mohd Abdul Fatah Abdul Manan Karen A Crouse M Ibrahim M Tahir Rozita Rosli Fiona N-F How David J Watkin Alexandra M Z Slawin |
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| Institution: | (1) Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 UiTM Shah Alam, Selangor, Malaysia;(2) Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia;(3) Department of Obstetrics and Gynaecology, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia;(4) Chemical Chemistry Research Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QA, UK;(5) Molecular Structure Laboratory, School of Chemistry, University of St. Andrews, St. Andrews, Fife, KY16 9ST, UK |
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| Abstract: | 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 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. |
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