Heterodimeric bis(amino thiol) complexes of oxorhenium(V) that mimic the structure of steroid hormones. Synthesis and stereochemical issues
- Univ. of Illinois, Urbana, IL (United States)
The authors have prepared a series of bis-bidentate complexes of rhenium that mimic the size, shape, and peripheral functionality of steroidal androgens. In a model system, the authors used 2D NMR and X-ray crystallographic analysis to show that adjacent N-methyl and oxo substitutents adopt an anti configuration during the coordination reaction. The authors have synthesized a bis-bidentate oxorhenium(V) complex whose structure and peripheral functionality mimic 5{alpha}-dihydrotestosterone. 2D-NMR analysis indicates that the N-methyl and oxo substituents are driven into the steroidal anti configuration ({beta}-N-methyl, {alpha}-oxo) by the {beta}-orientation of the methyl group equivalent to C-18. Thus, this metal complex provides a remarkable structural and stereochemical mimic of a steroid. Its in vivo stability, however, appears to be limited. 7 figs.
- OSTI ID:
- 495297
- Journal Information:
- Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 8 Vol. 61; ISSN JOCEAH; ISSN 0022-3263
- Country of Publication:
- United States
- Language:
- English
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