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Synthesis, Characterization and Cytotoxic Activity of S-Benzyldithiocarbazate Schiff Bases Derived from 5-Fluoroisatin, 5-Chloroisatin, 5-Bromoisatin and Their Crystal Structures

  • Mohd Abdul Fatah Abdul MananEmail author
  • Karen A. Crouse
  • M. Ibrahim M. Tahir
  • Rozita Rosli
  • Fiona N.-F. How
  • David J. Watkin
  • Alexandra M. Z. Slawin
Original Paper

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.

Graphical abstract

Schiff bases were prepared from S-benzyldithiocarbazate with 5-fluro-, 5-chloro- and 5-bromoisatin. They were found to be selectively active against MCF-7 cell line (Human non-metastatic mammary gland adenocarcinoma cell line) with the bromide compound was the most active with IC50 value of 6.40 μM (2.6 μg/mL).

Keywords

Dithiocarbazate Schiff base Isatin MCF-7 Structure 

Notes

Acknowledgments

We thank the Department of Chemistry, Universiti Putra Malaysia for the provision of laboratory facilities. This work was funded by a grant from the Ministry of Science, Technology and Innovation under the Intensification of Research in Priority Area program (Grant no. 09-02-04-0755-EA001). Support from Universiti Teknologi MARA (UiTM) and the Ministry of Higher Education (MOHE) for MAFA Manan is also gratefully acknowledged.

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Mohd Abdul Fatah Abdul Manan
    • 1
    Email author
  • Karen A. Crouse
    • 2
  • M. Ibrahim M. Tahir
    • 2
  • Rozita Rosli
    • 3
  • Fiona N.-F. How
    • 2
  • David J. Watkin
    • 4
  • Alexandra M. Z. Slawin
    • 5
  1. 1.Faculty of Applied SciencesUniversiti Teknologi MARAShah AlamMalaysia
  2. 2.Department of Chemistry, Faculty of ScienceUniversiti Putra MalaysiaSerdangMalaysia
  3. 3.Department of Obstetrics and Gynaecology, Faculty of Medicine and Health SciencesUniversiti Putra MalaysiaSerdangMalaysia
  4. 4.Chemical Chemistry Research LaboratoryUniversity of OxfordOxfordUK
  5. 5.Molecular Structure Laboratory, School of ChemistryUniversity of St. AndrewsFifeUK

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