Disease relevance of EINECS 246-995-7

• Studies with malaria-infected mice show that THQ PFTIs dramatically reduce parasitemia and lead to parasite eradication in the majority of animals [1].
• In the course of screening for free radical scavengers, rare metabolites, benzastatins A and B having aminobenzamide skeleton and benzastatins C and D having tetrahydroquinoline skeleton, were isolated from the culture broth of streptomyces nitrosporeus 30643 [2].

Psychiatry related information on EINECS 246-995-7

• The development of a novel series of tetrahydroquinoline-derived gamma-secretase inhibitors for the potential treatment of Alzheimer's disease is described [3].

High impact information on EINECS 246-995-7

• The resultant tyrosine 837 to cysteine alteration in the beta subunit corresponded to the binding site for the THQ and peptide substrate [4].
• The binding characteristics of [3H]L-689,560 [(+/-)-4-(trans)-2-carboxy-5,7-dichloro-4-phenylaminocarbonylamino -1,2,3,4- tetrahydroquinoline], a selective antagonist for the glycine site on the N-methyl-D-aspartate receptor, have been evaluated using rat cortex/hippocampus P2 membranes [5].
• Additional improvements in activity were obtained by modification of the substituents on the tetrahydroquinoline nitrogen, bringing the Ki of three of the compounds below 15 nM against the human TS enzyme [6].
• [reaction: see text] Highly enantioselective rhodium-catalyzed asymmetric hydrogenation (>98% ee) and Sharpless epoxidation (>90% ee) of o-nitrocinnamyl substrates lead to intermediates that can be transformed into tetrahydroquinoline derivatives [7].
• Previously, we have shown that parasites resistant to a tetrahydroquinoline (THQ)-based PFT inhibitor BMS-388891 have mutations leading to amino acid substitutions in PFT that map to the peptide substrate binding domain [8].

Biological context of EINECS 246-995-7

• The cytotoxicity of the extracts and pure tetrahydroquinoline alkaloids was assessed on the HeLa cell line and showed IC50 values ranging from 5.8 to above 50 microg/ml [9].
• Design, synthesis, and structure-activity relationships of tetrahydroquinoline-based farnesyltransferase inhibitors [10].
• Tetrahydroquinoline derivative rac-30 with a molecular weight of 517 and a log D(pH 7.4) of 1.9 displays potent and long lasting blood pressure lowering effects after oral administration to sodium depleted conscious marmosets [11].
• For substrates bearing simple alkyl groups, a substantial amount of tetrahydroquinoline derivatives were generated through 6-endo-trig cyclization [12].

Anatomical context of EINECS 246-995-7

• In this study, we evaluated the in vitro effects of the novel non-peptidic opioid 4-tyrosylamido-6-benzyl-1,2,3,4 tetrahydroquinoline (CGPM-9) on lymphocyte and macrophage functions [13].
• Differential effects of the novel non-peptidic opioid 4-tyrosylamido-6-benzyl-1,2,3,4 tetrahydroquinoline (CGPM-9) on in vitro rat t lymphocyte and macrophage functions [13].

Gene context of EINECS 246-995-7

• To identify neuroprotective agents after stroke, new substituted tetrahydroquinoline derivatives were designed as antagonists of the glycine binding site associated to the NMDA receptor, satisfying the key pharmacophoric requirements [14].
• Also, an unsubstituted 4-phenyl ring of the tetrahydroquinoline scaffold is favorable for their FSH receptor antagonistic activity [15].

Analytical, diagnostic and therapeutic context of EINECS 246-995-7

• Thus, a series of tetrahydroquinoline products were obtained in high purity by simple filtration, and the resin was recovered for reuse without loss of activity [16].
• The preferred conformation of the trans-2,4-disubstituted tetrahydroquinoline system, as shown by X-ray crystallography and 1H NMR studies, places the 2-carboxyl pseudoequatorial and the 4-substituent pseudoaxial [17].
• Galipea officinalis Hancock, a Venezuelan shrubby tree which is acclaimed in folk medicine for its many healing properties, is the only species of the genus to contain tetrahydroquinoline alkaloids [18].

References