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Title: | Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids |
Authors: | Thipphawan Chuprajob Chatchawan Changtam Ratchanaporn Chokchaisiri Warangkana Chunglok Nilubon Sornkaew Apichart Suksamrarn ทิพวรรณ จูประจบ ชัชวาลย์ ช่างทำ รัชนาพร โชคชัยสิริ วรางคณา จุ้งลก นิลุบล สอนแก้ว อภิชาต สุขสำราญ Ramkhamhaeng University. Faculty of Science Huachiew Chalermprakiet University. Faculty of Science and Technology University of Phayao. School of Science Walailak University. School of Allied Health Sciences and Public Health Ramkhamhaeng University. Faculty of Science Ramkhamhaeng University. Faculty of Science |
Keywords: | Oral -- Cancer ช่องปาก – มะเร็ง Trienone ไตรเอโนน Curcuminoids เคอร์คิวมินอยด์ Aldol condensations การควบแน่นแบบอัลดอล |
Issue Date: | 2014 |
Citation: | Bioorganic & Medicinal Chemistry Letters 24, 13, 1 July 2014 : 2839-2844 |
Abstract: | A general method for the synthesis of substituted (1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-ones, based on the aldol condensations of substituted 4-phenylbut-3-en-2-ones and substituted 3-phenylacrylaldehydes, was achieved. The natural trienones 4 and 5 have been synthesized by this method, together with the trienone analogues 9–20. These analogues were evaluated for their cytotoxic activity against human oral cancer KB cell line. The structure–activity relationship study has indicated that the analogues with the 1,4,6-trien-3-one function are more potent than the curcuminoid-type function. Analogues with meta-oxygen function on the aromatic rings are more potent than those in the ortho- and para-positions. Free phenolic hydroxy group is more potent than the corresponding methyl ether analogues. Among the potent trienones, compounds 11, 18 and 20 were more active than the anticancer drug ellipticine. All compounds were also evaluated against the non-cancerous Vero cells and it was found that compounds 11, 12 and 17 were much less toxic than curcumin (1); they showed high selectivity indices of 35.46, 33.46 and 31.68, respectively. These analogues are regarded as the potent trienones for anti-oral cancer study. |
URI: | https://has.hcu.ac.th/jspui/handle/123456789/4281 |
Appears in Collections: | Science and Technology - Articles Journals |
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