Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug
A new ferrocene complex, 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one dimethyl sulfoxide monosolvate, [Fe(C5H5)(C24H27O2)]·C2H6OS, has been synthesized and structurally characterized by single-crystal X-ray diffraction techniques. The molecule crystallizes in the space group P21 with o...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2016-06-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989016008446 |
| _version_ | 1798031756452954112 |
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| author | José A. Carmona-Negrón Mariola M. Flores-Rivera Zaibeth Díaz-Reyes Curtis E. Moore Arnold L. Rheigold Enrique Meléndez |
| author_facet | José A. Carmona-Negrón Mariola M. Flores-Rivera Zaibeth Díaz-Reyes Curtis E. Moore Arnold L. Rheigold Enrique Meléndez |
| author_sort | José A. Carmona-Negrón |
| collection | DOAJ |
| description | A new ferrocene complex, 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one dimethyl sulfoxide monosolvate, [Fe(C5H5)(C24H27O2)]·C2H6OS, has been synthesized and structurally characterized by single-crystal X-ray diffraction techniques. The molecule crystallizes in the space group P21 with one molecule of dimethyl sulfoxide. A hydrogen bond links the phenol group and the dimethyl sulfoxide O atom, with an O...O distance of 2.655 (5) Å. The ferrocene group is positioned in the β face of the estrone moiety, with an O—C—C—C torsion angle of 44.1 (5)°, and the carbonyl bond length of the hormone moiety is 1.216 (5) Å, typical of a C=O double bond. The average Fe—C bond length of the substituted Cp ring [Fe—C(Cp*)] is similar to that of the unsubstituted one [Fe—C(Cp)], i.e. 2.048 (3) versus 2.040 (12) Å. The structure of the complex is compared with those of estrone and ethoxymethylestrone. |
| first_indexed | 2024-04-11T20:01:31Z |
| format | Article |
| id | doaj.art-9d4db8c4ae474c07aca2cee9380ce146 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T20:01:31Z |
| publishDate | 2016-06-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-9d4db8c4ae474c07aca2cee9380ce1462022-12-22T04:05:34ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902016-06-0172686887110.1107/S2056989016008446bg2586Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drugJosé A. Carmona-Negrón0Mariola M. Flores-Rivera1Zaibeth Díaz-Reyes2Curtis E. Moore3Arnold L. Rheigold4Enrique Meléndez5University of Puerto Rico, Department of Chemistry, PO Box 9019, Mayaguez, PR 00681, Puerto RicoUniversity of Puerto Rico, Department of Chemical Engineering, PO Box 9000, Mayaguez, PR 00681, Puerto RicoUniversity of Puerto Rico, Department of Chemical Engineering, PO Box 9000, Mayaguez, PR 00681, Puerto RicoUniversity of California–San Diego, Department of Chemistry and Biochemistry, Urey Hall 5128, 9500 Gilman Drive, La Jolla, CA 92093-0358, USAUniversity of California–San Diego, Department of Chemistry and Biochemistry, Urey Hall 5128, 9500 Gilman Drive, La Jolla, CA 92093-0358, USAUniversity of Puerto Rico, Department of Chemistry, PO Box 9019, Mayaguez, PR 00681, Puerto RicoA new ferrocene complex, 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one dimethyl sulfoxide monosolvate, [Fe(C5H5)(C24H27O2)]·C2H6OS, has been synthesized and structurally characterized by single-crystal X-ray diffraction techniques. The molecule crystallizes in the space group P21 with one molecule of dimethyl sulfoxide. A hydrogen bond links the phenol group and the dimethyl sulfoxide O atom, with an O...O distance of 2.655 (5) Å. The ferrocene group is positioned in the β face of the estrone moiety, with an O—C—C—C torsion angle of 44.1 (5)°, and the carbonyl bond length of the hormone moiety is 1.216 (5) Å, typical of a C=O double bond. The average Fe—C bond length of the substituted Cp ring [Fe—C(Cp*)] is similar to that of the unsubstituted one [Fe—C(Cp)], i.e. 2.048 (3) versus 2.040 (12) Å. The structure of the complex is compared with those of estrone and ethoxymethylestrone.http://scripts.iucr.org/cgi-bin/paper?S2056989016008446crystal structureanticancer compoundferrocenemedicinal chemistry |
| spellingShingle | José A. Carmona-Negrón Mariola M. Flores-Rivera Zaibeth Díaz-Reyes Curtis E. Moore Arnold L. Rheigold Enrique Meléndez Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug Acta Crystallographica Section E: Crystallographic Communications crystal structure anticancer compound ferrocene medicinal chemistry |
| title | Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug |
| title_full | Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug |
| title_fullStr | Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug |
| title_full_unstemmed | Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug |
| title_short | Crystal structure of 16-ferrocenylmethyl-3β-hydroxyestra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug |
| title_sort | crystal structure of 16 ferrocenylmethyl 3β hydroxyestra 1 3 5 10 trien 17 one a potential chemotherapeutic drug |
| topic | crystal structure anticancer compound ferrocene medicinal chemistry |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989016008446 |
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