African Journal of

  • Abbreviation: Afr. J. Biotechnol.
  • Language: English
  • ISSN: 1684-5315
  • DOI: 10.5897/AJB
  • Start Year: 2002
  • Published Articles: 12278

Full Length Research Paper

Synthesis and antiproliferative activity of diethyl 5-acetyl-4-methyl- 6-(2-fluorophenylimino)-6H-thiopyran-2,3-dicarboxylate (3TM)

Tayebeh Baghipour1, Mohammad A. Khalilzadeh1, Mehdi Rajabi2 and Jamshid Mehrzad2
1Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran 2Department of Chemistry and Biochemistry, Neyshabur Branch, Islamic Azad University, Neyshabur, Iran.
Email: [email protected]

  •  Accepted: 08 July 2011
  •  Published: 19 October 2011


Diethyl 5-acetyl-4-methyl-6-(2-fluorophenylimino)-6H-thiopyran-2,3-dicarboxylate(3TM) was synthesized and the antiproliferative activity of 3TM is reported here. Compound 3TM inhibits the growth of human colon cancer HCT-15 with an IC50value of 4.5 µM and breast cancer MCF-7 with an IC50 value of 7 µM in a dose/time dependent manner by using sulforhodamine B assay. Moreover, suppression of clonogenic activity occurs after exposure to 3TM at a concentration of 3 µM for HCT-15 and of 5 µM for MCF-7. The effect of ligand complexation on DNA structure led to the overall affinity constant of K3M-DNA = 2.4  x 104 M-1.


Key words: Diethyl 5-acetyl-4-methyl-6-(2-fluorophenylimino)-6H-thiopyran-2,3-dicarboxylate (3TM), synthesis, antiproliferative activity.