67711-02-8Relevant academic research and scientific papers
Synthesis and Biological Activity of Novel Vitamin D Analogues: 24,24-Difluoro-25-hydroxy-26,27-dimethylvitamin D3 and 24,24-Difluoro-1α,25-dihydroxy-26,27-dimethylvitamin D3
Gill, Harpal S.,Londowski, James M.,Corradino, Robert A.,Zinsmeister, Alan R.,Kumar, Rajiv
, p. 480 - 490 (1990)
We synthesized 24,24-difluoro-25-hydroxy-26,27-dimethylvitamin D3 (16) and 24,24-difluoro-1α,25-dihydroxy-26,27-dimethylvitamin D3 (21), from 3β-hydroxy-22,23-dinorcholenic acid 3-acetate.Compound 16 was found to be a highly potent v
Synthesis of dinorcholane and 5β-cholane derivatives
Nahar, Lutfun,Turner, Alan B.
, p. 329 - 332 (2007/10/03)
The convenient synthesis of seven dinorcholane and 5β-cholane derivatives, 3β-acetoxy-23,24-dinorchol-5-en-22-oyl methoxy anhydride (2), 3β-acetoxy-23,24-dinorchol-5-en-22-oyl chloride (3), 3β-acetoxy-23,24- dinorchol-5-en-22-ol (4), 3α-acetoxy-5β-cholan-24-oic acid (6), 3α-acetoxy-5β-cholan-24-oic acid ethyl ester (7), 3-oxo-5β-cholan-24-oic acid (8) and 3-oxo-5β-cholan-24-oic acid ethyl ester (9) have been described. Full spectroscopic data for these compounds are presented.
The synthesis of a fluorescent cholesteryl oleate analogue
Best, Wayne M.,Mortimer, Bok-Cheng,Redgrave, Trevor G.,Stick, Robert V.
, p. 1243 - 1245 (2007/10/03)
A fluorescent analogue of cholesteryl oleate, namely 22-[ethyl(2′-naphthyl)amino]-23,24-dinorchol-5-en-3β-yl oleate, has been prepared from a steroidal carboxylic acid, 2-naphthylamine and oleic acid.
A Mechanism-Based Fluorogenic Probe for the Cytochrome P-450 Cholesterol Side Chain Cleavage Enzyme
Simpson, Daniel J.,Unkefer, Clifford J.,Whaley, Thomas W.,Marrone, Babetta L.
, p. 5391 - 5396 (2007/10/02)
The rate-limiting step of steroid biosynthesis is the enzymatic conversion of cholesterol to pregnenolone by cytochrome P-450scc (side chain cleavage) located in the inner mitochondrial membrane of all steroid producing cells.We report here the synthesis and application of a fluorogenic probe which is a cholene-based steroid with a fluorogenic moiety (resorufin) strategically located at the site of side chain cleavage.Synthesis of the probe required four steps starting from 3β-acetoxy-22,23-bisnor-5-cholenic acid and resorufin.Reaction of the probe with P-450scc yields pregnenolone and the highly fluorescent resorufin, thus providing a sensitive fluorescent signal representative of enzyme activity.The fluorescence quantum yield of this probe is approximately 40-fold lower (Φ = 0.006) than resorufin (Φ = 0.23) and is essentially nonfluorescent at wavelengths used to excite resorufin.The utility of the probe is demonstrated biochemically by incubation with mitochondria known to contain the P-450scc enzyme, and its specificity for this enzyme is shown by regulation of the enzyme activity with inhibitors and through the use of a nonspecific substrate.
LONG-ACTING CONTRACEPTIVE AGENTS: BILE ACID ESTERS OF NORETHISTERONE
Herz, J. E.,Sandoval, J.
, p. 327 - 332 (2007/10/02)
The synthesis of the esters of norethisterone (17α-ethynyl-17β-hydroxyestr-4-en-3-one) with three bile acids and of the cholesteryl carbonate of norethisterone are described.
