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. 2014 Nov 4;8:2161–2171. doi: 10.2147/DDDT.S69914

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© 2014 Zhang et al. This work is published by Dove Medical Press Limited, and licensed under Creative Commons Attribution – Non Commercial (unported, v3.0) License

The full terms of the License are available at http://creativecommons.org/licenses/by-nc/3.0/. Non-commercial uses of the work are permitted without any further permission from Dove Medical Press Limited, provided the work is properly attributed.

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The synthetic pathway for monocarbonyl curcumin analogs S1–S5, and AS1–AS29.

Note: Reagents and conditions were a) morpholine, p-TSA, cyclohexane, reflux, 50%; b) vanillin, EtOH, reflux, HCl, 30%; c) differently aldehydes, HCl gas, EtOH, 50°C–70°C, 10%–70%; d) THF, propionyl chloride, Et₃N, rt, 5%–54%; e) piperidone, pyrone, or thiopyrone, HCl gas, EtOH, rt, 40%–50%; f) THF, propionyl, or isobutyryl chloride, Et₃N, rt, 8%–31%; g) piperidone or pyrone, p-TSA, cyclohexane, reflux, 40%–50%; h) 2-chlorodebenzaldehyde, EtOH, reflux, HCl, 30%–35%; i) 3,4-dihydroxybenzaldehyde or 3,4,5-trimethoxybenzaldehyde, HCl gas, EtOH, rt, 10%–15%.

Abbreviations: AS, asymmetrical monocarbonyl curcumin derivative; EtOH, ethanol; Et₃N, triethylamine; Me, methyl; rt, room temperature; THF, tetrahydrofuran; TSA, toluenesulfonic acid; HCl, hydrochloric acid.