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Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids

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dc.contributor.author Thipphawan Chuprajob
dc.contributor.author Chatchawan Changtam
dc.contributor.author Ratchanaporn Chokchaisiri
dc.contributor.author Warangkana Chunglok
dc.contributor.author Nilubon Sornkaew
dc.contributor.author Apichart Suksamrarn
dc.contributor.author ทิพวรรณ จูประจบ
dc.contributor.author ชัชวาลย์ ช่างทำ
dc.contributor.author รัชนาพร โชคชัยสิริ
dc.contributor.author วรางคณา จุ้งลก
dc.contributor.author นิลุบล สอนแก้ว
dc.contributor.author อภิชาต สุขสำราญ
dc.contributor.other Ramkhamhaeng University. Faculty of Science en
dc.contributor.other Huachiew Chalermprakiet University. Faculty of Science and Technology en
dc.contributor.other University of Phayao. School of Science en
dc.contributor.other Walailak University. School of Allied Health Sciences and Public Health en
dc.contributor.other Ramkhamhaeng University. Faculty of Science en
dc.contributor.other Ramkhamhaeng University. Faculty of Science en
dc.date.accessioned 2025-07-06T07:11:16Z
dc.date.available 2025-07-06T07:11:16Z
dc.date.issued 2014
dc.identifier.citation Bioorganic & Medicinal Chemistry Letters 24, 13, 1 July 2014 : 2839-2844 en
dc.identifier.other https://doi.org/10.1016/j.bmcl.2014.04.105
dc.identifier.uri https://has.hcu.ac.th/jspui/handle/123456789/4281
dc.description.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. en
dc.language.iso en_US en
dc.subject Oral -- Cancer en
dc.subject ช่องปาก – มะเร็ง en
dc.subject Trienone en
dc.subject ไตรเอโนน en
dc.subject Curcuminoids en
dc.subject เคอร์คิวมินอยด์ en
dc.subject Aldol condensations en
dc.subject การควบแน่นแบบอัลดอล en
dc.title Synthesis, cytotoxicity against human oral cancer KB cells and structure–activity relationship studies of trienone analogues of curcuminoids en
dc.type Article en


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