5143-94-2Relevant articles and documents
Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs
Lee, Kiyoun,Poudel, Yam B.,Glinkerman, Christopher M.,Boger, Dale L.
, p. 5897 - 5905 (2015/08/03)
Abstract The total syntheses of dihydrolysergic acid and dihydrolysergol are detailed based on a Pd(0)-catalyzed intramolecular Larock indole cyclization for the preparation of the embedded tricyclic indole (ABC ring system) and a subsequent powerful inverse electron demand Diels-Alder reaction of 5-carbomethoxy-1,2,3-triazine with a ketone-derived enamine for the introduction of a functionalized pyridine, serving as the precursor for a remarkably diastereoselective reduction to the N-methylpiperidine D-ring. By design, the use of the same ketone-derived enamine and a set of related complementary heterocyclic azadiene [4+2] cycloaddition reactions permitted the late stage divergent preparation of a series of alternative heterocyclic derivatives not readily accessible by more conventional approaches.
Synthesis of European pharmacopoeial impurities A, B, C, and D of cabergoline
Wagger, Jernej,Pozes, Aljaz,Pozgan, Franc
, p. 23146 - 23156 (2013/11/19)
For the use of analytics, European pharmacopoeial impurities A, B, C, and D of cabergoline were synthesized. Ergocryptine was chosen as a starting material and synthesis was accomplished via two approaches, different in length and stereochemical outcome. A longer, indirect approach was realized through otherwise problematic oxidations of the 9,10-dihidrolysergol derivative, to the corresponding aldehyde and carboxylic acid. This was achieved by the use of activated DMSO and a Pinnick oxidation sequence. All four synthesized impurities are used as analytical standards in cabergoline manufacturing processes.
Ergoline derivatives as highly potent and selective antagonists at the somatostatin sst1 receptor
Troxler, Thomas,Enz, Albert,Hoyer, Daniel,Langenegger, Daniel,Neumann, Peter,Pfaeffli, Paul,Schoeffter, Philippe,Hurth, Konstanze
, p. 979 - 982 (2008/09/18)
Non-peptidic compounds containing the octahydro-indolo[4,3-fg]quinoline (ergoline) structural element have been optimized into derivatives with high affinity (pKd r sst1 > 9) and selectivity (>1000-fold for h sst1 over h sst2-h sst5) for the somatostatin sst1 receptor. In functional assays, these ergolines act as antagonists at human recombinant sst1 receptors. Pharmacokinetic studies in rodents reveal good oral bioavailability and brain penetration for some of these compounds.
