Please use this identifier to cite or link to this item: https://has.hcu.ac.th/jspui/handle/123456789/4281
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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