38199-31-4Relevant academic research and scientific papers
Iridium-Catalyzed Aza-Spirocyclization of Indole-Tethered Amides: An Interrupted Pictet-Spengler Reaction
Gabriel, Pablo,Gregory, Alex W.,Dixon, Darren J.
supporting information, p. 6658 - 6662 (2019/08/30)
A mild, reductive spirocyclization of indole-linked amides and lactams for the efficient and selective synthesis of aza-spirocyclic indoline products is described. The catalytic reductive activation of tertiary amides or lactams by Vaska's complex with tetramethyldisiloxane as the terminal reductant allowed iminium ion formation, before a diastereoselective 5-endo-trig spirocyclization of the tethered indole moiety was triggered. Terminal reduction affords the aza-spiroindoline products in an overall highly chemoselective and diastereoselective one-pot process.
Dopamine/serotonin receptor ligands. 10: SAR studies on azecine-type dopamine receptor ligands by functional screening at human cloned D1, D2L, and D5 receptors with a microplate reader based calcium assay lead to a novel potent D1/D5 selective antagonist
Hoefgen, Barbara,Decker, Michael,Mohr, Patrick,Schramm, Astrid M.,Rostom, Sherif A. F.,El-Subbagh, Hussein,Schweikert, Peter M.,Rudolf, Dirk R.,Kassack, Matthias U.,Lehmann, Jochen
, p. 760 - 769 (2007/10/03)
On the basis of the benz[d]indolo[2,3-g]azecine derivative 1 (LE300), structure-activity relations were investigated in order to identify the pharmacophore in this new class of ligands. Various structural modifications were performed and the inhibitory activities at human cloned D1, D2L, and D5 receptors were measured by using a simple fluorescence microplate reader based calcium assay. Subsequently, the affinities of active compounds were estimated by radioligand binding experiments, Deleting one of the aromatic rings as well as replacing it by a phenyl moiety abolishes the inhibitory activities almost completely. Contraction of the 10-membered central ring decreases them significantly. The replacement of indole by thiophene or N-methylpyrrole reduces the inhibitory activity, whereas replacing the indole by benzene increases it. Finally, the hydroxylated dibenz[d,g]azecine derivative 11d (LE404) was found to be more active than the lead 1 in the functional calcium assay as well as in radioligand displacement experiments.
New bis-indolic macrolactams
Henin,Noe,Laronze
, p. 1693 - 1703 (2007/10/03)
Treatment of several ω-halogenoamides, derived from tryptamine, with powdered potassium hydroxide in 1,2-dimethoxyethane in the presence of 18-crown-6, resulted in intramolecular and/or bimolecular cyclization, depending on the length of the chain and dilution conditions, to give macrocyclic compounds. Some of them were converted by a Bischler-Napieralski reaction, followed or not by reduction, to new tetracyclic derivatives of β-carbolines.
PREPARATION OF LACTAMS VIA OXIDATION OF CYCLIC, TERTIARY AND SECONDARY AMINES WITH Hg(II)-EDTA COMPLEX IN ALKALINE MEDIUM
Wenkert, Ernest,Angell, E. Charles
, p. 1331 - 1338 (2007/10/02)
Oxidation of N-alkylpiperidines and other cyclic, tertiary amines with Hg(II)-EDTA complex in basic solution yields lactams, similar oxidation of N-hydroxypiperidines gives hydroxamic acids (presumably via nitrones) and oxidation of N-unsubstituted piperidines affords lactams, probably via 1-piperidine trimers.
