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 Manan, Karen A. Crouse, M. Ibrahim M. Tahir, Rozita Rosli, Fiona N. -F. How, David J. Watkin, Alexandra M. Z. Slawin

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

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

Original languageEnglish
Pages (from-to)1630-1641
Number of pages12
JournalJournal of Chemical Crystallography
Volume41
Issue number11
DOIs
Publication statusPublished - Nov 2011

Keywords

  • Dithiocarbazate
  • Schiff base
  • Isatin
  • MCF-7
  • Structure
  • METAL-COMPLEXES
  • MANNICH-BASES
  • SCHIZOPYRENUS-RUSSELLI
  • DITHIOCARBAZIC ACID
  • CYSTICIDAL AGENTS
  • DERIVATIVES
  • ANTIBACTERIAL
  • INHIBITOR
  • ISATIN
  • ANTIFUNGAL

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