96553-75-2Relevant academic research and scientific papers
Stereoselective synthesis of (25r)-dafachronic acids and (25R)-cholestenoic acid as potential ligands for the DAF-12 receptor in Caenorhabditis elegans
Martin, René,Schmidt, Arndt W.,Theumer, Gabriele,Kurzchalia, Teymuras V.,Kn?lker, Hans-Joachim
, p. 1965 - 1968 (2008)
Commercially available diosgenin has been used as starting material for a highly efficient synthesis of (25R)-dafachronic acids and (25R)-cholestenoic acid, potential ligands for the receptor DAF-12 in the nematode Caenorhabditis elegans.
Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids
Brownholland, David P.,Covey, Douglas F.
, p. 22 - 31 (2017/03/24)
A synthetic route that utilizes a cross-metathesis reaction with Δ22 steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.
Inhibitory effect of oxygenated cholestan-3-ol derivatives on the growth of Mycobacterium tuberculosis
Schmidt, Arndt W.,Choi, Taylor A.,Theumer, Gabriele,Franzblau, Scott G.,Kn?lker, Hans-Joachim
, p. 6111 - 6113 (2013/11/06)
A variety of cholestan-3-ol derivatives, which are oxygenated at different positions of the steroid ring system, were prepared and tested for their inhibition of the Mycobacterium tuberculosis H37Rv strain. Several compounds showed significant antitubercular activities with MIC90 values in the range 4-8 μM and low or non-detectable toxicity against mammalian cells.
Stereoselective synthesis and hormonal activity of novel dafachronic acids and naturally occurring steroids isolated from corals
Saini, Ratni,Boland, Sebastian,Kataeva, Olga,Schmidt, Arndt W.,Kurzchalia, Teymuras V.,Kn?lker, Hans-Joachim
scheme or table, p. 4159 - 4163 (2012/07/14)
A stereoselective synthesis of (25S)-Δ1-, (25S)-Δ1,4-, (25S)-Δ1,7-, (25S)- Δ8(14)-, (25S)-Δ4,6,8(14)-dafachronic acid, methyl (25S)-Δ1,4-dafachronate and (25S)-5α-hydroxy-3,6- dioxocholest-7-en-26-oic acid is described. (25S)-Δ1,4- Dafachronic acid and its methyl ester are natural products isolated from corals and have been obtained by synthesis for the first time. (25S)-5α-Hydroxy- 3,6-dioxocholest-7-en-26-oic acid represents a promising synthetic precursor for cytotoxic marine steroids.
Synthesis and biological activity of the (25R)-cholesten-26-oic acids - Ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans
Martin, Rene,Schmidt, Arndt W.,Theumer, Gabriele,Krause, Tilo,Entchev, Eugeni V.,Kurzchalia, Teymuras V.,Knoelker, Hans-Joachim
experimental part, p. 909 - 920 (2009/05/30)
We describe the stereoselective transformation of diosgenin (4a) to (25R)-Δ4-dafachronic acid (1a), (25R)-Δ7- dafachronic acid (2a), and (25R)-cholestenoic acid (3a), which represent potential ligands for the hormonal receptor DAF-12
Synthesis and hormonal activity of the (25s)-cholesten-26-oic acids -potent ligands for the daf-12 receptor in caenorhabditis elegans
Martin, Rene,Entchev, Eugeni V.,Daebritz, Frank,Kurzchalia, Teymuras V.,Knoelker, Hans-Joachim
experimental part, p. 3703 - 3714 (2009/12/05)
Using a highly stereoselective Evans aldol reaction for the introduction of the stereogenic center at C-25, we describe an efficient synthesis of the orthogonally diprotected (25S)-26-hydroxycholesterol 11. In a few synthetic steps, this crucial intermediate 11 has been converted into the four (25S)-cholesten-26-oic acids 1-4, which have been obtained in 12-15 steps and 19-53% overall yield based on commercially available 3p-hydroxychol-5-en-24-oic acid (5). Our biological studies of the compounds 1-4 reveal that (25S)-Δ7-dafachronic acid (1) represents the most active steroidal ligand for the hormonal receptor DAF-12 in Caenorhabditis elegans. Moreover, the saturated (25S)-dafachronic acid (3) represents a new ligand for this receptor and the (25S)-steroidal acids are more active as compared to their corresponding (25R)-counterparts.
Stereoselective synthesis of the hormonally active (25S)- Δ7-dafachronic acid, (25S)-Δ4-dafachronic acid, (25S)-dafachronic acid, and (25S)-cholestenoic acid
Martin, Rene,Daebritz, Frank,Entchev, Eugeni V.,Kurzchalia, Teymuras V.,Knoelker, Hans-Joachim
scheme or table, p. 4293 - 4295 (2009/02/07)
We report a stereoselective synthesis of the (25S)-cholestenoic-26-acids which are highly efficient ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans.
Synthesis of the aglycone of the shark repellent pavoninin-4 using remote functionalization
Gong, Hua,Williams, John R.
, p. 2253 - 2255 (2007/10/03)
The aglycone of shark repellent pavoninin-4, (25R)-5α-cholestan- 3α,15α,26-triol 26-acetate 1a, was synthesized from (25R)-cholest-5-en-3β,-26-diol 4 (26-hydroxycholesterol) in eight steps in 18% overall yield. Breslow's remote functionalization strategy
Preparation of (25R)- and (25S)-26-functionalized steroids as tools for biosynthetic studies of cholic acids
Khripach, Vladimir A.,Zhabinskii, Vladimir N.,Konstantinova, Olga V.,Khripach, Natalya B.,Antonchick, Alexey V.,Antonchick, Andrey P.,Schneider, Bernd
, p. 551 - 562 (2007/10/03)
A new synthesis of both epimeric forms of 26-cholestanoic acids and 26-alcohols containing a 3β-hydroxy-Δ5- or a Δ4-3-keto-functionality in ring A is described starting from stigmasterol or (20S)-3β-acetoxy-pregn-5-en-20-carboxylic a
