Crystal Structure and Synthesis of Three New Steroidal Derivatives as Antiandrogens

Autor: Manuel Soriano-García, Norma Valencia, Tania Segura, Eugene Bratoeff, Marisa Cabeza
Rok vydání: 2010
Předmět:
Zdroj: Journal of Chemical Crystallography. 40:1119-1124
ISSN: 1572-8854
1074-1542
DOI: 10.1007/s10870-010-9806-7
Popis: The structures of 3β-cyclobutyl carbonyloxy-5-androsten-17-one (C24H34O3), compound 1; 3β-cyclopentyl carbonyloxy-5-androsten-17-one (C25H36O3), compound 2; and 3β-cyclohexyl carbonyloxy-5-androsten-17-one (C26H38O3) compound 3 were established by spectral and X-ray diffraction studies. Steroidal derivatives 1–3 exhibited a high antiandrogenic effect and could be considered as potential drugs for the treatment of prostate cancer. Compound 1 crystallizes in the orthorhombic space group P212121 with unit cell parameters a = 6.618(2), β = 14.167(3), c = 22.329(5) A, Z = 4. Compound 2 crystallizes in the orthorhombic space group P212121 with unit cell parameters a = 6.631(2), b = 13.865(4), c = 23.952(7) A, Z = 4. Compound 3 crystallizes in the orthorhombic space group P212121 with unit cell parameters a = 6.6100(9), b = 13.896(2), c = 24.491(3) A, Z = 4. All three structures (1–3) were solved by direct methods and refined to R = 0.0708, 0.0750 and 0.0496, respectively. For compound 2, there is positional disorder of the side chain at C3. All the rings of both steroid skeletons are trans connected. For structures 1–3, the six-membered rings A, B and C have a deformed chair, half chair and deformed chair conformations. The five-membered rings D adopt an intermediate envelope and half-chair conformations. For structure 2, the five-membered rings E and EA have a deformed envelope and an intermediate envelope and half-chair conformations, respectively. For structure 3, the six-membered ring E adopts a deformed chair conformation. Cohesion of the crystals can be attributed to van der Waals and weak C–H⋯O interactions. The crystal structures of three new steroidal derivatives as antiandrogens and their conformation were obtained by X-ray diffraction techniques from suitable single crystals. Steroidal derivatives 1–3 exhibited a high antiandrogenic effect and could be considered as potential drugs for the treatment of prostate cancer.
Databáze: OpenAIRE