337909-10-1

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate is used as a potential pharmaceutical intermediate for the development of new drugs due to its unique structural features and potential biological activities. Its complex molecular structure may allow for the creation of novel therapeutic agents with specific targeting and efficacy profiles.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate serves as a valuable compound for research purposes. It can be utilized in the design and synthesis of new chemical entities with potential therapeutic applications, contributing to the discovery of innovative treatments for various diseases and conditions.

Upstream product

• 88612-71-9 ethyl 4-oxo-4H-quinolizine-3-carboxylate 
• 68-12-2 N,N-dimethyl-formamide 
• 109-06-8 α-picoline 
• 40516-46-9 diethyl (ethoxymethylene)malonate 
• 101192-15-8 ethyl 3-ethoxy-2-ethoxycarbonyl-4-(pyridin-2-yl)butyrate 

Downstream Products

• 825628-77-1 1-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester 
• 852057-94-4 1-(2,7-difluoro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-4-oxo-4H-quinolizine-3-carboxylic acid 
• 1174207-47-6 ethyl 1-{[4-(4-cyanophenyl)piperazin-1-yl]methyl}-4-oxo-4H-quinolizine-3-carboxylate 
• 1221279-07-7 ethyl 1-[hydroxy(phenyl)methyl]-4-oxo-4H-quinolizine-3-carboxylate 
• 1181965-76-3 ethyl 4-oxo-1-({4-[4-(trifluoroethyl)phenyl]piperidin-1-yl}methyl)-4H-quinolizine-3-carboxylate 
• 1181964-81-7 C₂₂H₂₂N₂O₃ 
• 1181964-86-2 C₂₂H₂₁FN₂O₃ 
• 1181964-92-0 C₂₂H₂₁ClN₂O₃ 
• 1181964-88-4 C₂₂H₂₁FN₂O₃ 
• 1181964-84-0 C₂₂H₂₁FN₂O₃ 

Relevant academic research and scientific papers

A fluorescent activatable probe for imaging intracellular Mg2+

An activatable BODIPY probe for in vitro detection and fluorescence cell imaging of free Mg2+ without interference from Ca2+ is described. Fluorescence amplification of the probe is observed upon detection of physiological concentrations of Mg2+ due to reduced rotation of the fluorophore and effective chelation by a quinolizine-based core.

Discovery of a selective allosteric M1 receptor modulator with suitable development properties based on a quinolizidinone carboxylic acid scaffold

One approach to ameliorate the cognitive decline in Alzheimer's disease (AD) has been to restore neuronal signaling from the basal forebrain cholinergic system via the activation of the M1 muscarinic receptor. A number of nonselective M1 muscarinic agonists have previously shown positive effects on cognitive behaviors in AD patients, but were limited due to cholinergic adverse events thought to be mediated by the activation of the M2 to M5 subtypes. One strategy to confer selectivity for M1 is the identification of positive allosteric modulators, which would target an allosteric site on the M1 receptor rather than the highly conserved orthosteric acetylcholine binding site. Quinoline carboxylic acids have been previously identified as highly selective M1 positive allosteric modulators with good pharmacokinetic and in vivo properties. Herein is described the optimization of a novel quinolizidinone carboxylic acid scaffold with 4-cyanopiperidines being a key discovery in terms of enhanced activity. In particular, modulator 4i gave high plasma free fractions, enhanced central nervous system (CNS) exposure, was efficacious in a rodent in vivo model of cognition, and afforded good physicochemical properties suitable for further preclinical evaluation.

Quinolizidinone carboxylic acid selective M1 allosteric modulators: SAR in the piperidine series

SAR study of the piperidine moiety in a series of quinolizidinone carboxylic acid M1 positive allosteric modulators was examined. While the SAR was generally flat, compounds were identified with high CNS exposure to warrant additional in vivo evaluation.

Quinolizidinone carboxylic acids as CNS penetrant, selective M1 allosteric muscarinic receptor modulators

Positive allosteric modulation of the M1 muscarinic receptor represents an approach to treat the cognitive decline in patients with Alzheimer's disease. Replacement of a quinolone ring system in a quinolone carboxylic acid series of M1 modulators with a quinolizidinone bearing a basic amine linkage led to a series of compounds with higher free fraction, enhanced CNS exposure, and improved efficacy in rodent in vivo models of cognition.

Design, synthesis and anti-HIV integrase evaluation of 4-oxo-4H- quinolizine-3-carboxylic acid derivatives

4-Oxo-4H-quinolizine-3-carboxylic acid derivatives bearing sulfamido, carboxylamido, benzimidazole and benzothiazole substituents have been designed and synthesized. The structures of these new compounds were confirmed by 1H-NMR, 13C