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) A, β = 109.473 (1)°, V = 1239.1 (2) A3, 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.
Highlights
At the present time cancer still represents an enormous medical challenge
In this paper we describe the synthesis and X-ray determination of 3β-(p-iodobenzoyloxy)-16α,17α-epoxypregn-4-en-6,20-dione 7
Gonadectomies were performed under pentobarbital anesthesia 30 days prior to the experiments and the animals were sacrificed with CO2
Summary
At the present time cancer still represents an enormous medical challenge. It is predicted that in this year in the USA about 580,350 persons will die from this disease. Worldwide breast cancer represents the main cause of deaths for women [1] and prostate cancer for men [2]. (2014) Crystal Structure and Synthesis of 3β-(p-Iodobenzoyloxy)-16α,17α-Epoxypregn-4-En-6,20-Dione. The most extensively studied class of 5α-reductase inhibitors is the 4-azasteroids, which include the drug finasteride 1 This compound is the first 5α-reductase inhibitor approved in the USA for the treatment of BPH. Compound 7 is prepared from the commercially available 16-dehydropregnenolone acetate and its synthesis is shown in Scheme 1 This compound has a high biological activity with a good probability to be used in the future for the treatment of androgen dependent diseases [9] [10]
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