Crystal Structure and Synthesis of 17α-Acetoxy-pregn-4,6-diene-3,20-dione

Abstract

17α-Acetoxy-pregn-4,6-diene-3,20-dione (1), C23H30O4, was synthesized from the commercially available 17α-acetoxyprogesterone. X-ray diffraction analysis of (1) demonstrated that it consists 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; half chair and chair; and half chair conformations, respectively. The crystal of 17α-acetoxy-pregn-4,6-diene-3,20-dione is in orthorhombic crystal system with space group P212121, lattice constants: a = 10.843(1), b = 11.744(1), c = 15.815(2)A, V = 2013.9(4)A3, Dx = 1.222 g/cm3 and Z = 4. The molecules in the crystal are stabilized by C–H···O interactions and van der Waals forces. 17α-acetoxy-pregn-4,6-diene-3,20-dione (1) was synthesized. Compound 1 exhibited a high antiandrogenic effect and could be considered as a potential drug for the treatment of prostate cancer. The crystal structure of (1) was obtained by determination of X-ray diffraction from suitable single crystals.