Synthesis and Cytotoxic Evaluation of Monocarbonyl Analogs of Curcumin as Potential Anti‐Tumor Agents

Abstract

Preclinical Research A series of mono‐carbonyl curcumin analogs with different substituents at the 4/4’‐position of the phenyl group were synthesized and screened for in vitro cytotoxicity against a panel of human cancer cell lines using a methyl thiazolyl tetrazolium assay. Several of the curcumin analogs, especially B114, exhibited a wide‐spectrum of anti‐tumor properties in all tested cell lines, indicating their potential in as anti‐cancer lead compounds. Further toxicity testing in the NRK‐52E kidney cell line revealed that the analogs A111, A113, and B114 had comparable or higher safety than curcumin. These data suggested that the introduction of appropriate substituents in the 4/4’‐positions could be a promising approach for curcumin‐based drug design. Drug Dev Res 77 : 43–49, 2016. © 2016 Wiley Periodicals, Inc.

(2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells

“…The curcumin-like diarylpentanoid skeleton derivatives have been reported to exhibit a wide range of bioactivities, including antioxidant, anticancer, anti-inflammation, anti-melanogenesis, and anti-tyrosinase [ 13 , 14 , 15 , 16 , 17 , 18 ] activities. Especially, Leow et al [ 19 ] reported in 2014 that dibenzylidene-cyclopentanone scaffolds, including (2 E ,5 E )-2,5-bis(3-hydroxy-4-methoxybenzylidene)cyclopentanone (BHCP) ( Figure 1 ), might contribute to the protective effects on human osteosarcoma via regulation of the Wnt/β-catenin signaling pathway.…”

Design, synthesis and preliminary in-vitro studies of novel boronated monocarbonyl analogues of Curcumin (BMAC) for antitumor and β-amiloyd disaggregation activity

“…[21] MAC have attracted considerable attention because they feature greater stability than Curcumin, thus retaining or even increasing biological activity, while also improving pharmacokinetics. Interesting results have been reported in particular for MAC anti-inflammatory, [22] and anticancer activity, [23][24][25][26] (e.g., anti-prostate, [27,28] -breast, [29] -gastric [24,30] and -non-small-cell lung cancer [31][32][33]). A cell-apoptosis mechanism that is induced by endoplasmic reticulum stress has been hypothesised to explain these latter properties.…”

Green, rapid, and highly efficient syntheses of α,α′‐bis[(aryl or allyl)idene]cycloalkanones and 2‐[(aryl or allyl)idene]‐1‐indanones as potentially biologic compounds via solvent‐free microwave‐assisted Claisen–Schmidt condensation catalyzed by MoCl5

“…Also, compound i exhibited remarkable effects on anti‐proliferative activity and EGFR TK inhibitory activity . In 2016, Xu and co‐workers reported (2 E ,5 E )‐2,5‐bis(4‐[2‐hydroxyethoxy]‐3‐methoxybenzylidene)cyclopentanone ( j ), which showed potent cytotoxicity against human osteosarcoma cell lines U2‐OS and OS‐732, prostate cancer cell line PC‐3, and mouse mastocytoma cell line P815, implying their specific potential in the chemotherapy of cancer . Furthermore, Cheng and co‐workers introduced compound k as a coactivator‐associated arginine methyltransferase 1 (CARM 1) inhibitor .…”