34209-81-9Relevant articles and documents
Bismuth(III) triflate-catalyzed rearrangement of 16α,17α-epoxy-20-oxosteroids. Synthesis and structural elucidation of new 16α-substituted 17α-alkyl-17β-methyl-Δ13-18-norsteroids
Pinto, Rui M.A.,Salvador, Jorge A.R.,Le Roux, Christophe,Carvalho, Rui A.,Beja, Ana Matos,Paix?o, José A.
, p. 6169 - 6178 (2009)
The use of bismuth(III) triflate for the rearrangement of 16α,17α-epoxy-20-oxosteroids is reported. The reactions occur under truly catalytic conditions to afford novel 17α-alkyl-17β-methyl-Δ13-18-nor products bearing different O-containing substituents at C16. When the reaction is performed in the absence of acylation agent a mixture of isomeric 16α- and 16β-hydroxy derivatives is obtained, whereas when carried out in the presence of such reagents, the reaction selectively affords the corresponding 16α-acyl rearranged products. The chemoselective rearrangement of 5β,6β;16α,17α-diepoxy-20-oxopregnan-3β-yl acetate to afford a 'backbone' rearranged product bearing the 16α,17α-epoxide group is also reported. Some mechanistic considerations are provided. All rearranged products were the subject of comprehensive structural elucidation, by the use of X-ray crystallography and 2D NMR.
Evaluation of new pregnane derivatives as 5α-reductase inhibitor
Cabesa,Heuze,Bratoeff,Ramirez,Martinez
, p. 525 - 530 (2007/10/03)
The objective of this study was to synthesize several new pregnane derivatives and evaluate them as antiandrogens. From the commercially available 16-dehydropregnenolone acetate (7), two new steroidal compounds were synthesized: 17α-hydroxy-17β-methyl-16β-phenyl-D-homoandrosta-1,4.6- triene-3,20-dione (18) and 17α-acetoxy-17β-methyl-16β-phenyl-D-homoandrosta-1,4.6- triene-3,20-dione (19). The 5α-reductase inhibitory effect of the new compounds 18 and 19 together with the previously synthesized intermediates 7, 8, 13, 16, and 17 was determined in three different models: gonadectomized hamster flank organs diameter size, incorporation of [1,2-14C]sodium acetate into lipids in flank organs and conversion of [3H]testosterone (T) to [3H]dihydrotestosterone (DHT) by Penicillium crustosum. The evaluation of these steroids was carried out with three different controls: one group was treated with vehicle, the second with T and the third group with T plus finasteride. The pharmacological results from this work demonstrated that T significantly increases the diameter of the pigmented spot on the flank organs (p3H]T to [3H]DHT in a manner comparable to that of the flank organs. All experiments indicated that finasteride as well as steroids 7, 8, 13, 16-19 reduced significantly the conversion of T to DHT in P. crustosum. These compounds also decrease the size of the pigmented spot in the flank organs as well as reducing the incorporation of radiolabeled sodium acetate into lipids; T and the control sample (treated with vehicle only) were used for comparison. Apparently the presence of the 4,6-diene-3,20-dione moiety and also the C-17 ester group produce a higher inhibitory effect on the parameters used. PPThe data from this study indicated also that the three models used for the pharmacological evaluation exhibited comparable results.
17α-acetoxy-17β-methyl-16β-phenyl-D-homo-4,6-pregnadiene-3, 17a-dione: Synthesis and crystal structure determination of a new rearranged pregnane derivative
Soriano-Garcia, Manuel,Hernandez-Ortega, Simon,Bratoeff, Eugene,Valencia, Norma,Ramirez, Elena,Flores, Gregoria
, p. 487 - 491 (2007/10/03)
The title compound is C29H34O4, tetragonal, P43, a = b = 10.310(1), c = 23.871(2)A. The A, B, C, and D rings adopt envelope, half-chair, chair, and distorted chair conformations, respectively. The phenyl ring is planar. The methyl substituents at the A/B, C/D, and at C(17) are axial; and the -OCOCH3 group at C(17) and phenyl ring at C(16) are equatorial. The molecules in the crystal are held together by van der Waals forces and several C - H···O hydrogen bond interactions.
