TITLE:
Crystal Structure and Synthesis of 3β-(p-Iodobenzoyloxy)-16α,17α-Epoxypregn-4-En-6,20-Dione
AUTHORS:
Alejandra Chávez-Riveros, Marisa Cabeza, Eugene Bratoeff, Manuel Soriano-García
KEYWORDS:
Progesterone Derivatives, Androgen Receptor, 5-Alpha-Reductase Inhibitors, Human Prostate
JOURNAL NAME:
Crystal Structure Theory and Applications,
Vol.3 No.2,
June
25,
2014
ABSTRACT: 3β-(p-iodobenzoyloxy)-16α,17α-epoxypregn-4-en-6,20-dione
(7), C28H31O5I, was synthesized from the
commercially available 16-dehydropregnenolone acetate. X-ray diffraction
analysis of (1) demonstrated that it consisted of four rings, three
six-membered rings (A, B and C) and one five-membered ring (D). A, B, C and D
rings occur in an envelope, deformed chair, deformed chair, and the half chair conformations,
respectively. The absolute configurations of 7 for the chiral centers are 3S,
8S, 9S, 10R, 13S and 14S. The crystal of 3β-(p-iodobenzoyloxy)-16α,17α-epoxypregn-4-en-6,20-dione
is in monoclinic crystal system with space group P21, lattice constants: a = 10.8567 (11), b =
7.5479 (7), c = 16.0391 (16) Å, β = 109.473 (1)°, V = 1239.1 (2) Å3, Dx = 1.518 g/cm3 and Z = 2. The molecules in the crystal are
stabilized by C-H···O interactions and van der Waals forces.