Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity
Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids,...
Ausführliche Beschreibung
Autor*in: |
Marco A. Obregón-Mendoza [verfasserIn] María Mirian Estévez-Carmona [verfasserIn] Simón Hernández-Ortega [verfasserIn] Manuel Soriano-García [verfasserIn] María Teresa Ramírez-Apan [verfasserIn] Laura Orea [verfasserIn] Hugo Pilotzi [verfasserIn] Dino Gnecco [verfasserIn] Julia Cassani [verfasserIn] Raúl G. Enríquez [verfasserIn] |
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E-Artikel |
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Sprache: |
Englisch |
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2016 |
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Übergeordnetes Werk: |
In: Molecules - MDPI AG, 2003, 22(2016), 1, p 33 |
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Übergeordnetes Werk: |
volume:22 ; year:2016 ; number:1, p 33 |
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DOI / URN: |
10.3390/molecules22010033 |
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Katalog-ID: |
DOAJ007352093 |
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10.3390/molecules22010033 doi (DE-627)DOAJ007352093 (DE-599)DOAJe5da8f7587684e8787d2ce3ad798e3c8 DE-627 ger DE-627 rakwb eng QD241-441 Marco A. Obregón-Mendoza verfasserin aut Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds. retro-curcuminoids curcuminoid curcumin α,β-unsaturated-ketone dehydrozingerone Organic chemistry María Mirian Estévez-Carmona verfasserin aut Simón Hernández-Ortega verfasserin aut Manuel Soriano-García verfasserin aut María Teresa Ramírez-Apan verfasserin aut Laura Orea verfasserin aut Hugo Pilotzi verfasserin aut Dino Gnecco verfasserin aut Julia Cassani verfasserin aut Raúl G. Enríquez verfasserin aut In Molecules MDPI AG, 2003 22(2016), 1, p 33 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:22 year:2016 number:1, p 33 https://doi.org/10.3390/molecules22010033 kostenfrei https://doaj.org/article/e5da8f7587684e8787d2ce3ad798e3c8 kostenfrei http://www.mdpi.com/1420-3049/22/1/33 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 22 2016 1, p 33 |
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10.3390/molecules22010033 doi (DE-627)DOAJ007352093 (DE-599)DOAJe5da8f7587684e8787d2ce3ad798e3c8 DE-627 ger DE-627 rakwb eng QD241-441 Marco A. Obregón-Mendoza verfasserin aut Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds. retro-curcuminoids curcuminoid curcumin α,β-unsaturated-ketone dehydrozingerone Organic chemistry María Mirian Estévez-Carmona verfasserin aut Simón Hernández-Ortega verfasserin aut Manuel Soriano-García verfasserin aut María Teresa Ramírez-Apan verfasserin aut Laura Orea verfasserin aut Hugo Pilotzi verfasserin aut Dino Gnecco verfasserin aut Julia Cassani verfasserin aut Raúl G. Enríquez verfasserin aut In Molecules MDPI AG, 2003 22(2016), 1, p 33 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:22 year:2016 number:1, p 33 https://doi.org/10.3390/molecules22010033 kostenfrei https://doaj.org/article/e5da8f7587684e8787d2ce3ad798e3c8 kostenfrei http://www.mdpi.com/1420-3049/22/1/33 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 22 2016 1, p 33 |
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10.3390/molecules22010033 doi (DE-627)DOAJ007352093 (DE-599)DOAJe5da8f7587684e8787d2ce3ad798e3c8 DE-627 ger DE-627 rakwb eng QD241-441 Marco A. Obregón-Mendoza verfasserin aut Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds. retro-curcuminoids curcuminoid curcumin α,β-unsaturated-ketone dehydrozingerone Organic chemistry María Mirian Estévez-Carmona verfasserin aut Simón Hernández-Ortega verfasserin aut Manuel Soriano-García verfasserin aut María Teresa Ramírez-Apan verfasserin aut Laura Orea verfasserin aut Hugo Pilotzi verfasserin aut Dino Gnecco verfasserin aut Julia Cassani verfasserin aut Raúl G. Enríquez verfasserin aut In Molecules MDPI AG, 2003 22(2016), 1, p 33 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:22 year:2016 number:1, p 33 https://doi.org/10.3390/molecules22010033 kostenfrei https://doaj.org/article/e5da8f7587684e8787d2ce3ad798e3c8 kostenfrei http://www.mdpi.com/1420-3049/22/1/33 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 22 2016 1, p 33 |
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10.3390/molecules22010033 doi (DE-627)DOAJ007352093 (DE-599)DOAJe5da8f7587684e8787d2ce3ad798e3c8 DE-627 ger DE-627 rakwb eng QD241-441 Marco A. Obregón-Mendoza verfasserin aut Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds. retro-curcuminoids curcuminoid curcumin α,β-unsaturated-ketone dehydrozingerone Organic chemistry María Mirian Estévez-Carmona verfasserin aut Simón Hernández-Ortega verfasserin aut Manuel Soriano-García verfasserin aut María Teresa Ramírez-Apan verfasserin aut Laura Orea verfasserin aut Hugo Pilotzi verfasserin aut Dino Gnecco verfasserin aut Julia Cassani verfasserin aut Raúl G. Enríquez verfasserin aut In Molecules MDPI AG, 2003 22(2016), 1, p 33 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:22 year:2016 number:1, p 33 https://doi.org/10.3390/molecules22010033 kostenfrei https://doaj.org/article/e5da8f7587684e8787d2ce3ad798e3c8 kostenfrei http://www.mdpi.com/1420-3049/22/1/33 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 22 2016 1, p 33 |
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10.3390/molecules22010033 doi (DE-627)DOAJ007352093 (DE-599)DOAJe5da8f7587684e8787d2ce3ad798e3c8 DE-627 ger DE-627 rakwb eng QD241-441 Marco A. Obregón-Mendoza verfasserin aut Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity 2016 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds. retro-curcuminoids curcuminoid curcumin α,β-unsaturated-ketone dehydrozingerone Organic chemistry María Mirian Estévez-Carmona verfasserin aut Simón Hernández-Ortega verfasserin aut Manuel Soriano-García verfasserin aut María Teresa Ramírez-Apan verfasserin aut Laura Orea verfasserin aut Hugo Pilotzi verfasserin aut Dino Gnecco verfasserin aut Julia Cassani verfasserin aut Raúl G. Enríquez verfasserin aut In Molecules MDPI AG, 2003 22(2016), 1, p 33 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:22 year:2016 number:1, p 33 https://doi.org/10.3390/molecules22010033 kostenfrei https://doaj.org/article/e5da8f7587684e8787d2ce3ad798e3c8 kostenfrei http://www.mdpi.com/1420-3049/22/1/33 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 22 2016 1, p 33 |
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Retro-Curcuminoids as Mimics of Dehydrozingerone and Curcumin: Synthesis, NMR, X-ray, and Cytotoxic Activity |
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Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds. |
abstractGer |
Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds. |
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Curcumin and its derivatives have been extensively studied for their remarkable medicinal properties, and their chemical synthesis has been an important step in the optimization of well-controlled laboratory production. A family of new compounds that mimic the structure of curcumin and curcuminoids, here named retro-curcuminoids (7–14), was synthesized and characterized using 1D 1H- and 13C-NMR, IR, and mass spectrometry; the X-ray structure of 7, 8, 9, 10, 12, 13, and 14 are reported here for the first time. The main structural feature of these compounds is the reverse linkage of the two aromatic moieties, where the acid chloride moiety is linked to the phenolic group while preserving α, β-unsaturated ketone functionality. The cytotoxic screening of 7, 8, 9, and 10 at 50 and 10 µg/mL was carried out with human cancer cell lines K562, MCF-7, and SKLU-1. Lipid peroxidation on rat brain was also tested for compounds 7 and 10. Compounds 7, 8, and 10 showed relevant cytotoxic activity against these cancer cell lines, and 10 showed a protective effect against lipid peroxidation. The molecular resemblance to curcuminoids and analogs with ortho substituents suggests a potential source of useful bioactive compounds. |
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