132875-37-7

Usage

Chemical compound

4H-Imidazo[4,5,1-ij]quinolin-2(1H)-one,5-amino-5,6-dihydro-,(R)-(9CI)

Class

imidazoquinolinones

Structure

heterocyclic compound with an imidazoquinolinone core structure

Functional groups

amino group and dihydro group attached to the carbon atoms

Stereochemical configuration

(R)-(9CI)
Potential pharmacological properties
Suitable for further study in the fields of medicine and pharmaceuticals.

Upstream product

• 145554-63-8 (3R)-1,2,3,4-tetrahydroquinolin-3-amine 
• 121989-61-5 (R)-3-amino-1-methoxy-3,4-dihydroquinolin-2(1H)-one 
• 2448-45-5 Cbz-D-Phe 
• 673-06-3 D-(R)-phenylalanine 
• 1239015-96-3 methyl (3R)-3,8-diamino-3,4-dihydroquinoline-1(2H)-carboxylate 
• 1239015-88-3 (S)-4-benzyl-3-[(1aR,7bS)-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-3-carbonyl]oxazolidine-2-one 
• 1239015-87-2 (S)-4-benzyl-3-(1,2-dihydroquinoline-1-carbonyl)oxazolidin-2-one 
• 1239015-95-2 methyl (3R)-3-azido-6-bromo-8-nitro-3,4-dihydroquinoline-1(2H)-carboxylate 
• 1239015-94-1 methyl (3S)-6-bromo-3-[(methylsulfonyl)oxy]-8-nitro-3,4-dihydroquinoline-1(2H)-carboxylate 
• 1239015-93-0 methyl (3S)-6-bromo-3-hydroxy-8-nitro-3,4-dihydroquinoline-1(2H)-carboxylate 
• 1239015-92-9 methyl (3S)-6-bromo-3-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate 
• 1239015-91-8 methyl (3S)-3-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate 
• 91-22-5 quinoline 

Downstream Products

• 152886-85-6 U 91356 

Relevant academic research and scientific papers

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

Novel 1-, 5-, and 8-substituted analogues of sumanirole (1), a dopamine D2/D3 receptor (D2R/D3R) agonist, were synthesized. Binding affinities at both D2R and D3R were higher when determined in competition with the agonist radioligand [3H]7-hydroxy-N,N-dipropyl-2-aminotetralin (7-OH-DPAT) than with the antagonist radioligand [3H]N-methylspiperone. Although 1 was confirmed as a D2R-preferential agonist, its selectivity in binding and functional studies was lower than previously reported. All analogues were determined to be D2R/D3R agonists in both GoBRET and mitogenesis functional assays. Loss of efficacy was detected for the N-1-substituted analogues at D3R. In contrast, the N-5-alkyl-substituted analogues, and notably the n-butyl-arylamides (22b and 22c), all showed improved affinity at D2R over 1 with neither a loss of efficacy nor an increase in 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 D2R/D3R affinity and functional efficacy.

Remote control of the C-3-C-4 double-bond epoxidation of a chiral 1,2-dihydroquinoline: Application to the synthesis of (-)-(r)-sumanirole (PNU-95666E)

A twelve-step synthesis of (-)-(R)-sumanirole starting from quinoline is described. The first synthetic approach, using a chiral Reissert adduct, was too problematic to be pursued further. In the second successful approach, the authors took advantage of the stereoselective epoxidation of a 1,2-dihydroquinoline bearing an Evans' chiral auxiliary at N-1. A twelve-step synthesis of (-)-(R)-sumanirole hydrochloride has been developed from quinoline. In the successful approach, the key reaction is a diastereoselective epoxidation of the C-3-C-4 double bond of a 1,2-dihydroquinoline bearing a chiral oxazolidinone-derived auxiliary at N-1.