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Synthesis, Evaluation of Anticancer Activity and QSAR Study of Heterocyclic Esters of Caffeic Acid
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نویسنده
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Hajmohamad Ebrahim Ketabforoosh Shima ,Amini Mohsen ,Vosooghi Mohsen ,Shafiee Abbas ,Azizi Ebrahim ,Kobarfard Farzad
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منبع
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iranian journal of pharmaceutical research - 2013 - دوره : 12 - شماره : 4 - صفحه:705 -719
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چکیده
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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.
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کلیدواژه
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Caffeic acid; Mitsunobu; Electrooxidation; Cytotoxic activity.
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آدرس
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tehran university of medical sciences tums, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Department of Medicinal Chemistry, ایران, tehran university of medical sciences tums, Faculty of Pharmacy and Drug Design and Development Research Center, Department of Medicinal Chemistry, ایران, tehran university of medical sciences tums, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Department of Medicinal Chemistry, ایران, tehran university of medical sciences tums, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Department of Medicinal Chemistry, ایران, tehran university of medical sciences tums, Faculty of Pharmacy, Molecular Research Labratory, Department of Pharmacology and Toxicology, ایران, shahid beheshti university of medical sciences, School of Pharmacy and Phytochemistry Research Center, Department of Medicinal Chemistry, ایران
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پست الکترونیکی
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kobarfard@sbmu.ac.ir
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Authors
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Shima ,Mohsen ,Mohsen ,Abbas ,Ebrahim ,Farzad
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