4368-11-0Relevant academic research and scientific papers
HYDROXYSTEROID COMPOUNDS, THEIR INTERMEDIATES, PROCESS OF PREPARATION, COMPOSITION AND USES THEREOF
-
, (2016/02/09)
The present invention relates to novel steroidal compounds of formula (I), process for preparation of the same and composition comprising these compounds.
Efficient C-21 Deoxygenation of 21-Alkoxy-20-keto Corticoid Steroids with Trimethylsilyl Iodide in the Presence of Methanol
Nagaoka, Masao,Kunitama, Yurie,Numazawa, Mitsuteru
, p. 334 - 338 (2007/10/02)
Reaction of 21-alkyl ethers 1, 4-6, 8, and 9 with a large excess of trimethylsilyl iodide (TMSI) produced the deoxygenated products 3 and 11 in low to moderate yields along with a small amount of 21-alcohols 2 and 10.The deoxygenation reaction in the presence of 1.5 molar equiv of MeOH gave the products in much higher yields than those without MeOH, except the reaction of the ethyl and n-propyl ethers 4 and 5.Treatment of 1 and 8 with trimethylsilyl chloride/NaI in the presence of MeOH gave similar results to those with TMSI.Compound 3 was also produced in high yields by reaction of 1 and 4 with HI under mild conditions.On the other hand, treatment of 17α-ketol 7 with TMSI in the presence of MeOH yielded 17aβ-methyl D-homo steroid 15.The results along with deuterium-labeling experiments with MeOD and IR and 1H NMR spectral analysis during the reaction with TMSI suggest that dealkylation of the 21-alkyl ethers precedes the deoxygenation, in which HI produced in situ by reaction of MeOH with TMSI would be involved.
Amino-9,10-secosteroids useful for treating head injury, spinal cord trauma or stroke
-
, (2008/06/13)
The amino-9,10-secosteroids STR1 of the present invention contain an amino group attached to the terminal carbon atom of the C17 -side chain and are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc.
An Efficient and Short Degradation of the Cholic Acid Side Chain: A New Method for the Preparation and Dehydrogenation of 4,5-Dihydro-oxazoles
Barton, Derek H. R.,Motherwell, William B.,Wozniak, Jocelyne,Zard, Samir Z.
, p. 1865 - 1870 (2007/10/02)
11-Oxolithocholic acid (2) and other unhindered aliphatic carboxylic acids undergo an efficient, boric acid mediated, condensation with 2-amino-2-methylpropan-1-ol (3) to give the corresponding 4,5-dihydro-oxazoles.The latter can be dehydrogenated in high yield to the α,β-unsaturated derivatives (e.g. 18) with benzeneseleninic acid or anhydride.Acylation with trichloroacetyl chloride in the case of (18) followed by ozonolysis and saponification furnishes the 20-oxopregnane derivative (21) in over 80percent overall yield.The side chain can also be cleaved in one step by benzeneseleninic acid albeit in relatively low yield .
Steroids esterified in position 17 and thioesterified in position 21, a process for preparing them and their use as medicaments
-
, (2008/06/13)
Compounds of formula: STR1 wherein A and B each represent, independently of each other, a straight-chained or branched alkyl group having from 1 to 6 carbon atoms or a phenyl group optionally mono- or polysubstituted by alkyl radicals having from 1 to 6 carbon atoms, alkoxy groups having from 1 to 6 carbon atoms or halogen, T and U, independently of each other, represent hydrogen atoms or together form a double bond, V is a hydrogen atom or a methyl group at the α-position, W is a hydrogen atom or a halogen atom at the α-position, X is a hydroxy group at the β-position and Y is a hydrogen atom or X and Y may together represent an oxygen atom, and Z1 is a hydrogen atom, a methyl group at the α- or β-position, while Z2 is a hydrogen atom, or Z1 and Z2 together form a methylene group. These compounds have anti-inflammatory activity.
A Practical Catalytic Method for the Preparation of Steroidal 1,4-Dien-3-ones by Oxygen Atom Transfer from Iodoxybenzene to Diphenyl Diselenide
Barton, Derek H. R.,Godfrey, Christopher R. A.,Morzycki, Jacek W.,Motherwell, William B.,Ley, Steven V.
, p. 1947 - 1952 (2007/10/02)
The dehydrogenation of steroidal 3-ketones can be accomplished in high yield using benzeneseleninic anhydride generated in situ by efficient oxygen atom transfer from iodoxybenzene to catalytic amounts of diphenyl diselenide.An experimentally convenient and economical development of this catalytic cycle is the use of meta-iodoxybenzoic acid which both avoids chromatography and allows recovery of meta-iodobenzoic acid and diphenyl diselenide. 12-Hydroxy- and 12-keto-steroids are also dehydrogenerated very efficiently using this catalytic process.
Oxygen Atom Transfer from Iodylbenzene to Diphenyl Diselenide - A Convenient Method for Dehydrogenation of Steroidal 3-Ketones
Barton, Derek H. R.,Morzycki, Jacek W.,Motherwell, William B.,Ley, Steven V.
, p. 1044 - 1045 (2007/10/02)
Steroidal 3-ketones are smoothly dehydrogenated in high yield using benzeneseleninic anhydride generated in situ by oxygen atom transfer from iodylbenzene, PhIO2, to catalytic amounts of diphenyl diselenide; use of meta-iodylbenzoic acid in the above cycle has led to the development of an economical and experimentally convenient method avoiding chromatographic separations and with recovery of the m-iodobenzoic acid and the diphenyl diselenide.
