The molecular structure of 17-hydroxyprogesterone 17-(10-chloro-9-ketodecanoate) and 17-hydroxyprogesterone 17-(10-hydroxy-9-ketodecanoate)

Abstract

The steroid ester 17-hydroxyprogesterone 17-(10-chloro-9-ketodecanoate), CaIH4sOsCI, is a potent irreversible inhibitor of corticosteroid acetyltransferase while its analog, 17-hydroxyprogesterone 17-(I0-hydroxy-9-ketodecanoate), C31H4606, is not a good substrate. The structures of the two steroids were determined from room-temperature counter-collected X-ray data through the application of direct methods. The space group for both compounds is P21 with cell dimensions of a= 14.505 (3), b= 7.668 (2), c= 13.511 (3) ,~ and fl= 107.97 (2) ° for the chloro derivative and a= 14066 (9), b= 7666 (3), c=13.493 (5),~ and fl=106.03 ° for the hydroxy compound. The observed densities are dc~= 1.234 and do~= 1-202 g.cm -3, which are consistent with two molecules per unit cell and calculated densities dci = 1.235 and doll = 1.215 g.cm3. 3189 independent reflections were collected for the chloro derivate and 2667 for the hydroxy. The model of the chloro derivative was refined by conventional leastsquares techniques to an R index of 0069 while refinement of the hydroxy derivative was terminated at R = 0135. The conformations of the extended side chains are the same within experimental error except for the position of the terminal chloro and hydroxy groups. There are no significant intramolecular interactions.