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Carmona-Negrón JA, Flores-Rivera MM, Díaz-Reyes Z, et al. Crystal structure of 16-ferrocenylmethyl-3β-hydroxy-estra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug. Acta Crystallogr E Crystallogr Commun. 2016;72:868-71doi: 10.1107/S2056989016008446.
Carmona-Negrón, J. A., Flores-Rivera, M. M., Díaz-Reyes, Z., Moore, C. E., Rheigold, A. L., & Meléndez, E. (2016). Crystal structure of 16-ferrocenylmethyl-3β-hydroxy-estra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug. Acta crystallographica. Section E, Crystallographic communications, 72868-71. https://doi.org/10.1107/S2056989016008446
Carmona-Negrón, José A, et al. "Crystal structure of 16-ferrocenylmethyl-3β-hydroxy-estra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug." Acta crystallographica. Section E, Crystallographic communications vol. 72 (2016): 868-71. doi: https://doi.org/10.1107/S2056989016008446
Carmona-Negrón JA, Flores-Rivera MM, Díaz-Reyes Z, Moore CE, Rheigold AL, Meléndez E. Crystal structure of 16-ferrocenylmethyl-3β-hydroxy-estra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug. Acta Crystallogr E Crystallogr Commun. 2016 May 27;72:868-71. doi: 10.1107/S2056989016008446. eCollection 2016 Jun 01. PMID: 27308062; PMCID: PMC4908549.
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Acta Crystallogr E Crystallogr Commun. 2016 May 27;72:868-71. doi: 10.1107/S2056989016008446. eCollection 2016 Jun 01.

Crystal structure of 16-ferrocenylmethyl-3β-hydroxy-estra-1,3,5(10)-trien-17-one: a potential chemotherapeutic drug.

Acta crystallographica. Section E, Crystallographic communications

José A Carmona-Negrón, Mariola M Flores-Rivera, Zaibeth Díaz-Reyes, Curtis E Moore, Arnold L Rheigold, Enrique Meléndez

Affiliations

  1. University of Puerto Rico, Department of Chemistry, PO Box 9019, Mayaguez, PR 00681, Puerto Rico.
  2. University of Puerto Rico, Department of Chemical Engineering, PO Box 9000, Mayaguez, PR 00681, Puerto Rico.
  3. University of California-San Diego, Department of Chemistry and Biochemistry, Urey Hall 5128, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA.

PMID: 27308062 PMCID: PMC4908549 DOI: 10.1107/S2056989016008446

Abstract

A new ferrocene complex, 16-ferrocenylmethyl-3β-hy-droxy-estra-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 mol-ecule crystallizes in the space group P21 with one mol-ecule 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 eth-oxy-methyl-estrone.

Keywords: anti­cancer compound; crystal structure; ferrocene; medicinal chemistry

References

  1. Curr Med Chem. 2005;12(18):2075-94 - PubMed
  2. J Med Chem. 2006 Feb 23;49(4):1325-45 - PubMed
  3. Kidney Int. 2008 May;73(9):994-1007 - PubMed
  4. J Thorac Oncol. 2011 Aug;6(8):1400-6 - PubMed
  5. Dalton Trans. 2011 Oct 7;40(37):9557-65 - PubMed
  6. J Biol Inorg Chem. 2013 Feb;18(2):195-209 - PubMed
  7. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2013 Jun;69(Pt 3):249-59 - PubMed
  8. Anticancer Res. 2014 Apr;34(4):1609-15 - PubMed
  9. Acta Crystallogr A Found Adv. 2015 Jan;71(Pt 1):3-8 - PubMed
  10. Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8 - PubMed
  11. ChemMedChem. 2015 Jun;10(6):981-90 - PubMed
  12. Acta Crystallogr C Struct Chem. 2015 Dec 1;71(Pt 12):1100-5 - PubMed
  13. J Organomet Chem. 2014 Jan 1;749:204-214 - PubMed

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