Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds.

  title={Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds.},
  author={Malcolm W. Moon and J K Morris and Richard F. Heier and Constance G. Chidester and William E. Hoffmann and M. F. Piercey and John S. Althaus and Philip F. von Voigtlander and D. L. Evans and L. M. Figur},
  journal={Journal of medicinal chemistry},
  volume={35 6},
The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij] quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and… 
Pharmacology of U-91356A, an agonist for the dopamine D2 receptor subtype.
In rats, injection of U-91356A produced contralateral turning in rats with unilateral lesions of the substantia nigra, consistent with roles for the dopamine D2 receptor subtype as a dopamine autoreceptor and as a stimulatory, postsynaptic dopamine receptor.
Novel Analogues of (R)-5-(Methylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (Sumanirole) Provide Clues to Dopamine D2/D3 Receptor Agonist Selectivity
Computational modeling provided a structural basis for the D2R selectivity of 1, illustrating how subtle differences in the highly homologous orthosteric binding site (OBS) differentially affect D 2R/D3R affinity and functional efficacy.
Manufacture synthesis of 2,3-dihydropyrido[1,2,3-de]-1,4-benzoxazinium chlorides
Powerful irreversible inhibitors of monoamineoxidase (MAO) (EC have been discovered among 6-, 7-, and 8-(N-methyl-N-2-propynylaminomethyl)quinolines substituted in the carbocyclic ring.
Comparison of 5-HT1A and dopamine D2 pharmacophores. X-ray structures and affinities of conformationally constrained ligands.
Conformational and molecular mechanics studies of a new series of tricyclic ligands with affinity for either the dopamine D2 receptor or the 5-HT1A receptor, or both, has enabled us to elaborate
Synthesis of 2,3-dihidropyrido[1,2,3-de]-1,4-benzoxazinium chloride and some of its derivatives substituted in the carbocyclic ring
Among 6-, 7-, and 8-(N-methyl-N-propyn-2-ylaminomethyl)quinolines substituted in the carbocyclic ring, potent irreversible inhibitors ofmonoamino oxidase (MAO) (EC 1.4,3.4) were discovered, acting at
Synthesis, Pharmacological Investigation and Computational Studies on a Tricyclic Ergoline Analog with Selective Dopamine Autoreceptor Activity
Comparison of ab initio based molecular electrostatic isopotential maps corroborates the hypothesis that the dopamine structure 6, containing an intramolecular hydrogen bond donating effect of the meta‐HO‐group, represents the conformation which is active at the dopamine D‐2 autoreceptor.
Design, synthesis and inhibitory activity against Mycobacterium tuberculosis thymidine monophosphate kinase of acyclic nucleoside analogues with a distal imidazoquinolinone.
Interestingly, these non-planar compounds were similarly potent against the target enzyme than their aromatic analogues, suggesting a bioisosteric behavior that may also be applied to other biologically active compounds.
Synthesis of (R)-5-(Di[2,3-3H2]propylamino)5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one ([3H]U-86170) and (R)-5-([2,3-3H2]Propylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one ([3H]U-91356)
(R)-5-(diallylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (12b) was prepared in 9% overall yield from 3-aminoquinoline. Reaction of 12b in ethyl acetate with tritium gas in presence of
Synthesis of benzo[1,2-d;3,4-d']diimidazole and 1H-pyrazolo[4,3-b]pyridine as putative A2A receptor antagonists.
The synthesis and the binding affinity for the putative adenosine receptor antagonist 6-methyl-7-[1,2,3]triazol-2-yl-1,6-dihydrobenzo[1,2-d;3,4-d']diimidazole (10) and
Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions
A review of the recent literature is given focusing on synthetic approaches to 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1h)-quinolones using domino reactions, with a brief discussion of mechanism, scope, yields, simplicity and potential utility.