title: [Steroid ligands of androgen binding protein. The enantiomers of trans-trans and cis-trans perhydrohexestrols and trans-trans perhydrodiketones].
abstract: In the framework of a study on nonsteroidal androgens, the authors previously observed that in perhydrohexestrol series, the (+/-)-[(cis-4 hydroxycyclohexyl)-4(trans-4 hydroxycyclohexyl)-hexane] or cis-trans perhydrohexestrol and especially the (+/-)-(3,4 bis (trans-4-oxocyclohexyl)-hexane) or trans-trans perhydrodiketone, there is no affinity for AR (androgen receptor of the prostate) but they bind with high and specific affinity to the testosterone binding sites on ABP (epididymal androgen-binding protein). In this work, we describe the preparation, the stereochemistry and biological activities of trans-trans and cis-trans perhydrohexestrols and of trans-trans perhydrodiketone as well as their corresponding enantiomers. Biologically the tests AR and ABP are negative for the trans-trans perhydrohexestrol and of trans-trans perhydrodiketone and for its enantiomers. However for the enantiomers of cis-trans perhydrohexestrol and of trans-trans perhydrodiketone, the affinity of the (+) enantiomer for ABP is superior to that of the racemic and that of the (-) enantiomer, whereas the affinity for AR are zero. Chemically, the stereochemistry of the three racemics has been established by X-ray crystallographic analysis or by 1H n.m.r. The n.m.r. spectra have been analyzed in terms of chemical shifts and coupling constants.
mesh_terms: D000727:Androgen-Binding Protein / Q000378:metabolism*; D000818:Animals; D001665:Binding Sites; D002352:Carrier Proteins / Q000378:metabolism*; D003460:Crystallization; D004822:Epididymis / Q000378:metabolism; D006589:Hexestrol / Q000031:analogs & derivatives* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D011467:Prostate / Q000378:metabolism; D051381:Rats; D011919:Rats, Inbred Strains; D013237:Stereoisomerism; D014965:X-Rays
chemical_list: D000727:Androgen-Binding Protein; D002352:Carrier Proteins; D006589:Hexestrol; C035467:perhydrodiketohexestrol; C035468:perhydrohexestrol
vernacular_title: Sur les ligands stéroïdoïdes  de l'androgen binding protein,. Les énantiomères des trans-trans et cis-trans perhydrohexestrols et trans-trans perhydrodicétones.