Luminescent rhenium fac-tricarbonyl-containing complexes of androgenic oxo-steroids

Abstract

A new route to luminescent derivatives of androgenic steroids containing a ketone group in the 3-or 17-position has been developed. Reaction with the fac-Re(CO) 3 Cl complex of 3,3'-diamino-2,2'-bipyridine (complex 1) afforded a cyclic aminal product with different steroids. The rate of reaction and yield varies according to the conjugation or steric hindrance around the ketone group.

Single amino acid chelate complexes of the M(CO)3+ core for correlating fluorescence and radioimaging studies (M = 99mTc or Re)

“…This general strategy for the preparation of fluorescent complexes may be effectively extended to other biomolecules . Our initial excursion in this domain was the design of Re(CO) 3 + complexes of SAAC‐biotin analogues .…”

Tricarbonylchlorido(6′,7′-dihydro-5′H-spiro[cyclopentane-1,6′-dipyrido[3,2-d:2′,3′-f][1,3]diazepine]-κ2N1,N11)rhenium(I)

“…For a review of the photophysical properties of Re-polypyridyl complexes, see: Coleman et al (2008). For the synthesis of [Re(3,3 0 -diamino-2,2 0 -bipyridine)(CO) 3 Cl] and for the preparation of oxo-steroid derivatives of [Re(3,3 0 -diamino-2,2 0 -bipyridine)(CO) 3 Cl], see: Bullock et al (2012). For the reaction of [Re(3,3 0 -diamino-2,2 0 -bipyridine)(CO) 3 Cl] with ketones, see: Clayton et al (2008).…”

“…The title complex was prepared as part of a larger study into conjugation of [Re(3,3′-diamino-2,2′-bipyridine)(CO) 3 Cl] with oxo-steroids to form luminescent derivatives (Bullock et al 2012). These steroids contain a cyclopentyl ring (ring D) with a ketone group in the 17-position; therefore, cyclopentanone was used as a model compound to examine the potential reactivity of such steroids with the rhenium complex.…”

Tricarbonylchlorido(6′,7′-dihydro-5′H-spiro[cyclohexane-1,6′-dipyrido[3,2-d:2′,3′-f][1,3]diazepine]-κ2N1,N11)rhenium(I)

“…The title complex was prepared as part of a larger study into conjugation of [Re(3,3′-diamino-2,2′-bipyridine)(CO) 3 Cl] with oxo-steroids to form luminescent derivatives (Bullock et al 2012). These steroids contain a cyclohexyl ring (ring A) with a ketone group in the 3-position; therefore, cyclohexanone was used as a model compound to examine the potential reactivity of such steroids with the rhenium complex.…”