Title of article
Synthesis, Evaluation of Anticancer Activity and QSAR Study of Heterocyclic Esters of Caffeic Acid
Author/Authors
Hajmohamad Ebrahim Ketabforoosh, Shima Department of Medicinal Chemistry - Faculty of Pharmacy and Pharmaceutical Sciences Research Center -Tehran University of Medical Sciences , Amini, Mohsen Department of Medicinal Chemistry - Faculty of Pharmacy and Drug Design and Development Research Center -Tehran University of Medical Sciences , Vosooghi, Mohsen Department of Medicinal Chemistry - Faculty of Pharmacy and Pharmaceutical Sciences Research Center -Tehran University of Medical Sciences , Shafiee, Abbas Department of Medicinal Chemistry - Faculty of Pharmacy and Pharmaceutical Sciences Research Center -Tehran University of Medical Sciences , Azizi, Ebrahim Molecular Research Laboratory - Department of Pharmacology and Toxicology - Faculty of Pharmacy - Medical Sciences - University of Tehran , Kobarfard, Farzad Department of Medicinal Chemistry - School of Pharmacy and Phytochemistry Research Center - Shahid Beheshti University of Medical Sciences, Tehran
Pages
15
From page
705
To page
719
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 benzenesulfinate and sodium toluensulfinate as nucleophiles. Both heterocyclic 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.
Keywords
Caffeic acid , Mitsunobu , Electrooxidation , Cytotoxic activity
Journal title
Astroparticle Physics
Serial Year
2013
Record number
2415065
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