1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane
Ferrociphenols are anticancer organometallic molecules bearing a ferrocene group linked, at least, to one <i>para</i>-phenol moiety via a double bond. Up to the present, their biological activity has been thought to be linked to their oxidation within cells to form a reactive quinone-met...
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MDPI AG
2024-12-01
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| Online Access: | https://www.mdpi.com/1422-8599/2024/4/M1932 |
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| author | Jérémy Forté Patrick Herson Pascal Pigeon |
| author_facet | Jérémy Forté Patrick Herson Pascal Pigeon |
| author_sort | Jérémy Forté |
| collection | DOAJ |
| description | Ferrociphenols are anticancer organometallic molecules bearing a ferrocene group linked, at least, to one <i>para</i>-phenol moiety via a double bond. Up to the present, their biological activity has been thought to be linked to their oxidation within cells to form a reactive quinone-methide metabolite with the participation of this central double bond. To prove this assertion, the alkenyl entity of ferrociphenol <b>1a</b> (1,1-bis-(4-hydroxyphenyl)-2-ferrocenylbut-1-ene) was reduced by triethylsilane in an acidic medium to obtain the alkyl counterpart 1,1-bis(4-hydrophenyl)-2-ferrocenylbutane. 1,1-bis(4-hydrophenyl)-2-ferrocenylbutane was fully characterized by <sup>1</sup>H NMR (including COSY), <sup>13</sup>C NMR, HRMS, IR, elemental analysis and X-ray diffraction (XRD). Although missing the central double bond, this compound remains biologically active, opening the way to a new family of anticancer ferrocene-containing molecules. |
| format | Article |
| id | doaj-art-5b0880173eaa46ee999f6eebf80f7921 |
| institution | DOAJ |
| issn | 1422-8599 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj-art-5b0880173eaa46ee999f6eebf80f79212025-08-20T02:43:20ZengMDPI AGMolbank1422-85992024-12-0120244M193210.3390/M19321,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutaneJérémy Forté0Patrick Herson1Pascal Pigeon2CNRS, Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université, 4 Place Jussieu, 75005 Paris, FranceCNRS, Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université, 4 Place Jussieu, 75005 Paris, FranceCNRS, Institut Parisien de Chimie Moléculaire (IPCM), Sorbonne Université, 4 Place Jussieu, 75005 Paris, FranceFerrociphenols are anticancer organometallic molecules bearing a ferrocene group linked, at least, to one <i>para</i>-phenol moiety via a double bond. Up to the present, their biological activity has been thought to be linked to their oxidation within cells to form a reactive quinone-methide metabolite with the participation of this central double bond. To prove this assertion, the alkenyl entity of ferrociphenol <b>1a</b> (1,1-bis-(4-hydroxyphenyl)-2-ferrocenylbut-1-ene) was reduced by triethylsilane in an acidic medium to obtain the alkyl counterpart 1,1-bis(4-hydrophenyl)-2-ferrocenylbutane. 1,1-bis(4-hydrophenyl)-2-ferrocenylbutane was fully characterized by <sup>1</sup>H NMR (including COSY), <sup>13</sup>C NMR, HRMS, IR, elemental analysis and X-ray diffraction (XRD). Although missing the central double bond, this compound remains biologically active, opening the way to a new family of anticancer ferrocene-containing molecules.https://www.mdpi.com/1422-8599/2024/4/M1932ferroceneferrociphenolalkene reductionanticancer moleculesorganometallic compoundsX-ray diffraction |
| spellingShingle | Jérémy Forté Patrick Herson Pascal Pigeon 1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane Molbank ferrocene ferrociphenol alkene reduction anticancer molecules organometallic compounds X-ray diffraction |
| title | 1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane |
| title_full | 1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane |
| title_fullStr | 1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane |
| title_full_unstemmed | 1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane |
| title_short | 1,1-Bis(4-hydroxyphenyl)-2-ferrocenylbutane |
| title_sort | 1 1 bis 4 hydroxyphenyl 2 ferrocenylbutane |
| topic | ferrocene ferrociphenol alkene reduction anticancer molecules organometallic compounds X-ray diffraction |
| url | https://www.mdpi.com/1422-8599/2024/4/M1932 |
| work_keys_str_mv | AT jeremyforte 11bis4hydroxyphenyl2ferrocenylbutane AT patrickherson 11bis4hydroxyphenyl2ferrocenylbutane AT pascalpigeon 11bis4hydroxyphenyl2ferrocenylbutane |