95841-71-7Relevant academic research and scientific papers
A Concise Synthesis of 24,25-Dihydro-6- epi -Monanchosterol A
Taspinar, ?mer,Stojadinovic, Vladimir Kjartan,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther
supporting information, p. 1085 - 1088 (2021/05/13)
We report the first synthetic entry to a steroid with an unusual bicyclo[4.3.1]dec-3-en-10-one A/B ring substructure as a close structural analogue of the anti-inflammatory monanchosterols. Under optimized conditions, regioselective cis -dihydroxylation o
Synthesis of new alkylaminooxysterols with potent cell differentiating activities: Identification of leads for the treatment of cancer and neurodegenerative diseases
De Medina, Philippe,Paillasse, Michael R.,Payre, Bruno,Silvente-Poirot, Sandrine,Poirot, Marc
experimental part, p. 7765 - 7777 (2010/08/03)
We describe here the syntheses and the biological properties of new alkylaminooxysterols. Compounds were synthesized through the trans-diaxial aminolysis of 5,6-α-epoxysterols with various natural amines including histamine, putrescine, spermidine, or spermine. The regioselective synthesis of these 16 new 5α-hydroxyl-6β-aminoalkylsterols is presented. Compounds were first screened for dendrite outgrowth and cytotoxicity in vitro, and two leads were selected and further characterized. 5α-Hydroxy-6β-[2- (1Himidazol-4-yl)ethylamino]cholestan-3β-ol, called dendrogenin A, induced growth control, differentiation, and the death of tumor cell lines representative of various cancers including metastatic melanoma and breast cancer. 5α-Hydroxy-6β-[3-(4-aminobutylamino)propylamino]cholest-7-en- 3β-ol, called dendrogenin B, induced neurite outgrowth on various cell lines, neuronal differentiation in pluripotent cells, and survival of normal neurones at nanomolar concentrations. In summary, we report that two new alkylaminooxysterols, dendrogenin A and dendrogenin B, are the first members of a class of compounds that induce cell differentiation at nanomolar concentrations and represent promising new leads for the treatment of cancer or neurodegenerative diseases.
Synthesis of the marine epoxy sterol 9α,11α-epoxy-5α-cholest-7-ene-3β,5,6β-triol
Migliuolo, Anna,Notaro, Giacomo,Piccialli, Vincenzo,Sica, Donato
, p. 154 - 158 (2007/10/02)
The synthesis of 9α,11α-epoxy-5α-cholt'st-7-ene-3β,5,6β-triol (1), a highly oxygenated marine sterol containing a 9,11-epoxide moiety in the nucleus, is described. Epoxy sterol 1 was synthesized from cholesta-5,7-dien-3β-ol. Oxidation of this sterol with m-chloroperbenzoic acid followed by hydrolysis and acetylotion furnished 5α-cholest-7-ene-3β,5,6α-triol 3,6-diacetate (2). Mercuric acetate dehydrogenation of diacetate 2, followed by oxidation with manganese dioxide and epoxidation with m-chloroperbenzoic acid, afforded 9α,11α-epoxy-3β,5-dihydroxy-5α-cholest-7-en-6-one (5). Reduction of 5 with lithium aluminum hydride gave the desired compound 1. The structures of all synthetic intermediates were confirmed by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. A reassignment of resonances for carbons 1, 8, and 15 in the 13C NMR spectrum of 1, based on 2D-NMR correlation spectroscopy, has been accomplished.
Stereoselective Synthesis and Solvolytic Behavior of the Isomeric 7-Dehydrocholesterol 5,6-Oxides
Michaud, Dennis P.,Nashed, Nashaat T.,Jerina, Donald M.
, p. 1835 - 1840 (2007/10/02)
Cholesterol oxide hydrolase is recently described mammalian enzyme which catalyzes the hydration of Δ5-sterol oxides to 5,6-glycols in the liver.As the isomeric 7-dehydrocholesterol 5,6-oxides represent useful mechanistic probes of the action of the enzyme, synthetic procedures were sought for the stereoselective preparation of these unstable epoxides.Direct epoxidation of 7-dehydrocholesterol with peracid in the presence of aqueous buffer stereoselectively provided the α-oxide 2b in good yield.Synthesis of the β-oxide 12 proved more difficult in that attemptedformation of an intermediate bromohydrin with appropriate stereochemistry proved unsatisfactory.The finding that 7α-bromocholesteryl benzoate undergoes selective β-epoxidation and that the desired Δ7-double bond could be formed by treatment with potassium tert-butoxide resulted in the successful synthesis of the β- oxide 12.Both epoxides undergo cis addition of benzoic acid in chloroform at the allylic carbon and trans addition of 2-mercaptoethanol in base at the same position.Hydrolytic reactions prove to be more complex.Aqueous acid hydrolysis of the α-oxide 2b produced triol 5a and dienediol 6, which can further dehydrate to the trienol 7.Under identical conditions the β-oxide 12 hydrolyzes to a single product.Both epoxides, particulary the β-oxide 12, proved to be effective inhibitors of cholesterol oxide hydrolase.
