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

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

doi:10.1107/S2056989016008446

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(Pt 6):868-71. doi: 10.1107/S2056989016008446. eCollection 2016 Jun 1.

Authors

José A Carmona-Negrón¹, Mariola M Flores-Rivera², Zaibeth Díaz-Reyes², Curtis E Moore³, Arnold L Rheigold³, Enrique Meléndez¹

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.

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.