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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| author | Zlatko Lozanovski Ivana Todorovska Katerina Dragarska Jane Bogdanov |
| author_facet | Zlatko Lozanovski Ivana Todorovska Katerina Dragarska Jane Bogdanov |
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| description | 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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| spelling | doaj-art-6fd14adf68e048fbb0ab9b0bac8ff1ac2024-12-27T14:17:16ZengMDPI AGChemistry Proceedings2673-45832023-11-01141710.3390/ecsoc-27-16084Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiolZlatko Lozanovski0Ivana Todorovska1Katerina Dragarska2Jane Bogdanov3Higher Medical School, St. Kliment Ohridski University, Partizanska bb, 7000 Bitola, North MacedoniaInstitute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University in Skopje, Arhimedova 5, 1000 Skopje, North MacedoniaInstitute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University in Skopje, Arhimedova 5, 1000 Skopje, North MacedoniaInstitute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss. Cyril and Methodius University in Skopje, Arhimedova 5, 1000 Skopje, North MacedoniaThe 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>.https://www.mdpi.com/2673-4583/14/1/7monocarbonyl analogs of curcuminsymmetrical 2-bromobenzylidene MACssynthesis2-(dimethylamino)ethanethiolMichael reaction with thiolsUV-Vis spectroscopy |
| spellingShingle | Zlatko Lozanovski Ivana Todorovska Katerina Dragarska Jane Bogdanov Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiol Chemistry Proceedings monocarbonyl analogs of curcumin symmetrical 2-bromobenzylidene MACs synthesis 2-(dimethylamino)ethanethiol Michael reaction with thiols UV-Vis spectroscopy |
| title | Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiol |
| title_full | Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiol |
| title_fullStr | Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiol |
| title_full_unstemmed | Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiol |
| title_short | Synthesis of Symmetrical Monocarbonyl Analogs of Curcumin Containing a 2-Bromobenzylidene Moiety and Spectrophotometric Assessment of Their Reactivity with 2-(Dimethylamino)ethanthiol |
| title_sort | synthesis of symmetrical monocarbonyl analogs of curcumin containing a 2 bromobenzylidene moiety and spectrophotometric assessment of their reactivity with 2 dimethylamino ethanthiol |
| topic | monocarbonyl analogs of curcumin symmetrical 2-bromobenzylidene MACs synthesis 2-(dimethylamino)ethanethiol Michael reaction with thiols UV-Vis spectroscopy |
| url | https://www.mdpi.com/2673-4583/14/1/7 |
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