Synthesis, Evaluation of Anticancer Activity and QSAR Study of Heterocyclic Esters of Caffeic Acid

Authors

  • Abbas Shafiee Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran.
  • Ebrahim Azizi Molecular Research Laboratory, Department of Pharmacology and Toxicology, Faculty of Pharmacy, Medical Sciences, University of Tehran, Tehran, Iran.
  • Farzad Kobarfard Department of Medicinal Chemistry, Shahid Beheshti School of Pharmacy, Tehran, Iran.
  • Mohsen Amini Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran.
  • Mohsen Vosooghi Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran.
  • Shima H. M. Ebrahim Ketabforoosh Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran.
Abstract:

 Caffeic acid phenethyl ester(CAPE) suppresses the growth of transformed cells such as human breast cancer cells, hepatocarcinoma , myeloid leukemia, colorectal cancer cells, fibrosarcoma, glioma and melanoma. A group of heterocyclic esters of caffeic acid was synthesized using Mitsunobu reaction and the esters were subjected to further structural modification by electrooxidation of the catechol ring of caffeic acid esters in the presence of sodium benenesulfinate and sodium toluensulfinate as nucleophiles. Both heterocycle esters of caffeic acid and their arylsulfonyl derivatives were evaluated for their cytotoxic activity against HeLa, SK-OV-3, and HT-29 cancer cell lines. HeLa cells showed the highest sensitivity to the compounds and heterocyclic esters with no substituent on catechol ring showed better activity compared to their substituted counterparts. QSAR studies reemphasized the importance of molecular shape of the compounds for their cytotoxic activity.

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Journal title

volume 12  issue 4

pages  705- 719

publication date 2013-11-01

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