Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiol
The cross-conjugated dienones containing the 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore have diverse biological activities. These sometimes-called monocarbonyl analogs of curcumin (MACs) have especially pronounced biological activity when containing an electron-withdrawing group at the ortho-pos...
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| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-11-01
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| Series: | Chemistry Proceedings |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2673-4583/14/1/7 |
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| Summary: | The cross-conjugated dienones containing the 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore have diverse biological activities. These sometimes-called monocarbonyl analogs of curcumin (MACs) have especially pronounced biological activity when containing an electron-withdrawing group at the ortho-position of the benzene ring. Their biological activity most likely stems from a selective Michael reaction with thiols. It has been reported in the literature that certain MACs (in particular, <b>EF24</b>) react as electrophiles with glutathione and form bis adducts in vitro. Five MACs were prepared ((<i>2E</i>,<i>5E</i>)-2,5-bis(2-bromobenzylidene)cyclopentanone, (<b>2BrCP</b>), (<i>2E</i>,<i>6E</i>)-2,6-bis(2-bromobenzylidene)cyclohexanone (<b>2BrCX</b>, <b>B2BrBC</b>), (<i>2E</i>,<i>6E</i>)-2,6-bis(2-bromobenzylidene)- 4-<i>tert</i>-butyl-cyclohexanone (<b>4tB2BrCX</b>), (3<i>E</i>,5<i>E</i>)-3,5-bis(2-bromobenzylidene)-4-piperidone, (<b>2Br4PIP</b>) and (<i>3E</i>,<i>5E</i>)-3,5-bis(2-fluorobenzylidene)-4-piperidone, <b>EF24</b>), purified and characterized by spectroscopic means. The relative reactivity of these MACs towards 2-(dimethylamino)ethanethiol was assessed via a previously developed UV-Vis spectroscopic method and compared to <b>EF24</b>, which reacts readily in solution with thiols such as glutathione and cysteamine. All of the bis(2-bromobenzylidene) MACs react slower with 2-(dimethylamino)ethanethiol in 80:20 (v/v) acetonitrile/water compared to <b>EF24</b>. The relative reactivity of the analogs with 2-(dimethylamino)ethanethiol followed the order <b>EF24</b> > <b>2Br4PIP</b> > <b>2BrCX</b> > <b>2BrCP</b> > <b>4tB2BrCX</b>. |
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| ISSN: | 2673-4583 |