THE ANGULAR TRIFLUOROMETHYL GROUP .5. TOTAL SYNTHESIS AND BIOLOGICAL PROPERTIES OF 14-DEHYDRO-18,18,18-TRIFLUORO-19-NORTESTOSTERONE

Authors
HADDAD M BLAZEJEWSKI JC WAKSELMAN C DORAI V DUC I
Citation
M. Haddad et al., THE ANGULAR TRIFLUOROMETHYL GROUP .5. TOTAL SYNTHESIS AND BIOLOGICAL PROPERTIES OF 14-DEHYDRO-18,18,18-TRIFLUORO-19-NORTESTOSTERONE, European journal of medicinal chemistry, 29(7-8), 1994, pp. 627-634
Citations number
48
Categorie Soggetti
Chemistry Medicinal
Journal title
European journal of medicinal chemistry → ACNP
ISSN journal
02235234
Volume
29
Issue
7-8
Year of publication
1994
Pages
627 - 634
Database
ISI
SICI code
0223-5234(1994)29:7-8<627:TATG.T>2.0.ZU;2-Y
Abstract
The total synthesis of the 18,18,18-trifluoro analogue (FDNT) of 14-de hydro-19-nortestosterone (DNT) was performed using the intramolecular Diels-Alder reaction of an ortho-quinodimethane. Unlike 18,18,18-trifl uoro-19-nortestosterone (FNT), FDNT showed in vitro and in vivo biolog ical properties (binding affinity for the androgen receptor and growth stimulation of ventral prostate and seminal vesicles) comparable with its unfluorinated counterpart (DNT). The diverging behaviour of FNT a nd FDNT is tentatively ascribed to a difference in ring-D geometry.