4192-93-2Relevant academic research and scientific papers
Synthesis and 5α-reductase inhibitory activity of C21 steroids having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-oximes
Kim, Sujeong,Kim, Yong-Ung,Ma, Eunsook
, p. 355 - 368 (2012)
The synthesis and evaluation of 5α-reductase inhibitory activity of some 4-Azasteroid-20-ones and 20-oximes and 3β-hydroxy-, 3β-Acetoxy-, or epoxy-substituted C21 steroidal 20-ones and 20-oximes having double bonds in the A and/or B ring are described. Inhibitory activity of synthesized compounds was assessed using 5α-reductase enzyme and [1,2,6,7-3H]testosterone as substrate. All synthesized compounds were less active than finasteride (IC50: 1.2 nM). Three 4-Azasteroid-2-oximes (compounds 4, 6 and 8) showed good inhibitory activity (IC50: 26, 10 and 11 nM) and were more active than corresponding 4-Azasteroid 20-ones (compounds 3, 5 and 7). 3β-Hydroxy-, 3β-Acetoxyand 1α,2α-, 5α,6α- or 6α,7α-epoxysteroid-20-one and -20-oxime derivatives having double bonds in the A and/or B ring showed no inhibition of 5α-reductase enzyme.
Synthesis of pregnane derivatives, their cytotoxicity on LNCaP and PC-3 cells, and screening on 5α-reductase inhibitory activity
Kim, Sujeong,Ma, Eunsook
experimental part, p. 4655 - 4668 (2010/04/06)
A series of epoxy-and/or 20-oxime pregnanes were synthesized from commercially available pregnenolone. Compounds 1, 3, 7, 8 and 11-13 were evaluated for cytotoxicity activity towards LNCaP (androgen-dependent) and PC-3 (androgenindependent) prostate cancer cells. Compound 13 showed the highest activity on both LNCaP (IC50 15.17 μM) and PC-3 (IC50 11.83 μM) cell lines. Compound 11 showed weak activity on LNCaP cells (IC50 71.85 μM) and 8 showed the weak activity on PC-3 cells (IC50 68.95 μM), respectively. The 5α-reductase II (5AR2) inhibitory effects of compounds 1-3, 5 and 7-13 were investigated in a convenient screening model, in which compounds 5, 8, 11 and 12 were observed to be potential inhibitors of 5α-reductase, in particular, the 4-azasteroid 11, that also inhibited cell proliferation of androgen-dependent cells and 8, that in addition inhibited PC-3 cells more potently than LNCaP cells.
SYNTHESIS OF Δ6-, Δ1,6-, AND Δ1,6,16-PROGESTERONE
Kogan, N. A.,Raskin, L. M.,Vlasova, M.I.,Kul'bitskaya, S. M.
, p. 883 - 884 (2007/10/02)
The reaction of bromine and progesterone in a molar ratio of 2:1 leads to the formation mainly of 2,6-dibromoprogesterone, while reaction in a ratio of 3:1 gives 2,6,16-tribromoprogesterone.Their dehydrobromination in boiling lutidine leads to Δ1,6- and Δ1,6,16-progesterone.The dehydrogenation of progesterone by chloranil in tert-butyl alcohol gives Δ6-progesterone with a yield of 48percent.
