The iodo-Tamoxifens: molecular structures and syntheses of estrogens for external imaging of carcinoma

Authors:
  • DHDuncan H. Hunter
    Duncan H. Hunter
  • NPNicholas C. Payne
    Nicholas C. Payne
  • ARAsadur Rahman
    Asadur Rahman
  • JRJohn F. Richardson
    John F. Richardson
  • YPYolanda Zea Ponce
    Yolanda Zea Ponce
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Abstract
The E- and Z-isomers of an iodo-Tamoxifen 1 (1-(p-(β-dimethylaminoethoxy)phenyl)-2-(p-iodophenyl)-1-phenyl-1-butenes) have been prepared from the corresponding E- and Z-amino-Tamoxifens 2 (2-(p-aminophenyl)-1-(p-(β-dimethylaminoethoxy)phenyl)-1-phenyl-1-butenes) and the molecular structures have been determined from three dimensional X-ray data. Crystals of E-1 are triclinic, space group [ ], with Z = 2 in a cell of dimensions a = 10.714(2), b = 14.125(3), c = 8.240(2) Å, α = 95.78(1), β = 92.91(1), and γ = 71.41(1)°; those of Z-1 are monoclinic, space group P21/n, with Z = 4 and cell dimensions a = 12.675(2), b = 19.553(3), c = 9.483(1) Å, and β = 92.22(1)°. Intensity data collected on an automated four circle diffractometer were used for full-matrix least-squares refinement on F, which converged for E-1 at R = 0.054, 2736 observations, and for Z-1 at R = 0.042, 3644 observations. The solution of these structures determines the configuration of these isomers as well as the respective amino precursors and allows an unambiguous assignment of the proton nmr spectra of 1, 2 and the Tamoxifens.