16126-32-2Relevant articles and documents
Modification in the side chain of solomonsterol A: Discovery of cholestan disulfate as a potent pregnane-X-receptor agonist
Sepe, Valentina,Ummarino, Raffaella,D'Auria, Maria Valeria,Lauro, Gianluigi,Bifulco, Giuseppe,D'Amore, Claudio,Renga, Barbara,Fiorucci, Stefano,Zampella, Angela
experimental part, p. 6350 - 6362 (2012/09/05)
Seven synthetic analogues of the PXR (pregnane-X-receptor) potent natural agonist solomonsterol A were prepared by total synthesis. Their activity toward PXR was assessed by transactivation and RT-PCR assays. The study discloses cholestan disulfate (8) as a new, simplified agonist of PXR. By in vitro studies on hepatic cells we have demonstrated that this compound is a potent PXR agonist and functional characterization in human macrophages and hepatic stellate cells provided evidence that cholestan disulfate (8) has the ability to modulate the immune response triggered by bacterial endotoxin as well as to counter-activate hepatic stellate cell activation induced by thrombin. Because inhibition of immune-driven circuits might have relevance in the treatment of inflammation and liver fibrosis, the present data support the development of cholestan disulfate (8) in preclinical models of inflammatory diseases. The Royal Society of Chemistry 2012.
Regioselective enzymatic acylation of vicinal diols of steroids
Silva, M. Manuel Cruz,Riva, Sergio,Sá E Melo, M. Luisa
, p. 3065 - 3073 (2007/10/03)
Monoacylated derivatives of a complete set of 2,3- and 3,4-vicinal diols of steroids were prepared by regioselective lipase-catalysed transesterification reactions. The enzymes displayed different selectivities towards the vicinal diols depending on the configuration of the hydroxyl groups.
Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
Garrido Santos, Gustavo A.,Murray, Ana P.,Pujol, Carlos A.,Damonte, Elsa B.,Maier, Marta S.
, p. 125 - 132 (2007/10/03)
Five new steroid sulfates, sodium 2β,3α-dihydroxy-5α-cholestane 3-sulfate (6), sodium 2β,3α-dihydroxy-5α-cholestane 2-sulfate (7), disodium 2β,3α-dihydroxy-5α-cholestane disulfate (8), sodium 3α-acetoxy-2β-hydroxy-5α-cholestane 2-sulfate (12), and sodium
AN ALTERNATIVE ROUTE TO 2α,3α-DIOLS FROM 2,3-UNSATURATED 5α-STEROIDS AVOIDING THE USE OF OSMIUM TETRAOXIDE
Cerny, Vaclav
, p. 2211 - 2217 (2007/10/02)
A method for preparation of 2α,3α-dihydroxy-5α-steroids from 2,3-unsaturated 5α-steroids without the use of OsO4 is described.It involves the sequence of epoxidation, cleavage of the oxirane ring by HI, acetylation, oxidative replacement of iodine by hydroxyl and alkaline hydrolysis (I-IV) without purification of the intermediates.The presence of a 6-keto group does not decrease the yields.The yields are comparable with those obtained by osmylation and the method can find general use, particularly in the synthesis of brassinolide analogs.
Steroids. LXIX. Cyclisation Reactions of Vicinal Substituted Halogen Carbamoyloxy Steroids
Ponsold, K.,Grosse, P.
, p. 801 - 818 (2007/10/02)
Vicinal halogen urethanes of the cholestane, androstane and estratriene series react by heating under solvolytic conditions to cyclic carbonates of the corresponding cis-diols.By heating under basic conditions the same compounds react preferably to 2-oxazolidinones and if the basic conditions are strong enough by hydrolysis of the oxazolidinones to cis-amine alcohols too.Connections between the nature of the substituent at the urethane group or the steric arrangement of the vicinal groups on one hand and the reactivity to ring closure on the other hand are presented.
