2013
DOI: 10.1016/j.tet.2013.04.083
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Conjugate addition of curcumins to chalcones and azodicarboxylates

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Cited by 14 publications
(13 citation statements)
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“…As it was shown that the free hydroxyl groups of curcumin attached to the aromatic ring are modified by liver, kidney, and intestinal mucosa, produces curcumin glucuronide and curcumin sulfate, which results in low bioactivity343536, we expect that the selected analogs (−OH substituted with −OMe and −OCH 2 Ph) might show higher bioactivity. All these compounds were synthesized by condensation of acetyl acetone with aromatic aldehyde and the products were purified by re-crystallization or by silica gel column chromatography as reported earlier313738394041.…”
Section: Resultsmentioning
confidence: 99%
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“…As it was shown that the free hydroxyl groups of curcumin attached to the aromatic ring are modified by liver, kidney, and intestinal mucosa, produces curcumin glucuronide and curcumin sulfate, which results in low bioactivity343536, we expect that the selected analogs (−OH substituted with −OMe and −OCH 2 Ph) might show higher bioactivity. All these compounds were synthesized by condensation of acetyl acetone with aromatic aldehyde and the products were purified by re-crystallization or by silica gel column chromatography as reported earlier313738394041.…”
Section: Resultsmentioning
confidence: 99%
“…Previous study from our group showed reduction in cellular toxicity of α-Syn aggregates owing to minimized hydrophobic surface exposure due to binding of curcumin 27 . In our current study, we preferentially selected (from already synthesized curcumin analogs library 31 32 33 ) some curcumin analogs with different substitution on the aromatic ring that could affect the hydrophobicity of parental compound and thereby will help to bind with the oligomers and fibrils with a greater extent. In order to alter the hydrophobicity of the analogs, the compounds were selected in such a way that hydroxyl group of curcumin was replaced by −OMe (C2, C4 and C5) and −OCH 2 Ph (C6) groups ( Fig.…”
Section: Resultsmentioning
confidence: 99%
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“…Different attempts were made to modify curcumin moiety to obtain chemically stable curcumin analogs at physiological pH and it includes prominent organocatalytic cascade/domino reactions of multifunctional nucleophiles of curcumin . Each of the previously mentioned methods has their own merits, with at least one of the limitations in terms of the use of excess amount of expensive catalysts, multi‐step reactions, product diversity and column chromatography separations and low conversion with longer reaction period.…”
Section: Introductionmentioning
confidence: 99%