1620486-52-3

Usage

Molecular structure

1-oxo-3-(pyridin-3-yl)-2-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid has a complex structure with a tetrahydroisoquinoline core, a pyridine ring, a trifluoroethyl group, and a carboxylic acid functional group.

Functional groups

The compound contains a pyridine ring, which is a six-membered aromatic ring with one nitrogen atom, a trifluoroethyl group (CF3), and a carboxylic acid group (COOH).

Potential applications

This chemical may have potential applications in medicinal chemistry, as tetrahydroisoquinoline derivatives have been investigated for their pharmacological properties.

Pharmacological properties

The compound's pharmacological properties include potential antipsychotic, anti-inflammatory, and anti-tumor activities.

Research and development

The unique structure and functional groups of 1-oxo-3-(pyridin-3-yl)-2-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid make it a promising candidate for further research and development in the pharmaceutical and biotechnology industries.

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 1424799-68-7 (pyridine-3-ylmethylene)(2,2,2-trifluoroethyl)amine 
• 1620486-55-6 C₁₇H₁₃F₃N₂O₃*C₈H₁₁NO*C₃H₈O 

Downstream Products

• 1620486-55-6 C₁₇H₁₃F₃N₂O₃*C₈H₁₁NO*C₃H₈O 
• 1424799-20-1 (3S,4S)-N-(3-cyano-4-fluorophenyl)-1-oxo-3-(pyridin-3-yl)-2-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinoline-4-carboxamide 
• 1424799-20-1 SJ733 

Relevant academic research and scientific papers

Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides

Phenotypic whole-cell screening in erythrocytic cocultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent antimalarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure-activity studies revealed relationships between potency and modifications at N-2, C-3, and C-4. Careful structure-property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicological effects, inherent in the more potent primary screening hits such as 10b. Analogues 13h and 13i, with structural modifications at each site, were shown to possess excellent antimalarial activity in vivo. The (+)-(3S,4S) enantiomer of 13i and similar analogues were identified as the more potent. On the basis of these studies, we have selected (+)-13i for further study as a preclinical candidate.

N-methylimidazole promotes the reaction of homophthalic anhydride with imines

The addition of N-methylimidazole (NMI) to the reaction of homophthalic anhydride with imines such as pyridine-3-carboxaldehyde-N-trifluoroethylimine (9) reduces the amount of elimination byproduct and improves the yield of the formal cycloadduct, tetrahydroisoquinolonic carboxylate 10. Carboxanilides of such compounds are of interest as potential antimalarial agents. A mechanism that rationalizes the role of NMI is proposed, and a gram-scale procedure for the synthesis and resolution of 10 is also described.