24805-58-1

Upstream product

• 1135-12-2 p-benzylaniline 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 60-29-7 diethyl ether 
• 24805-59-2 diethyl {[(4-benzylphenyl)amino]methylidene}propanedioate 

Downstream Products

• 254883-07-3 ethyl 6-benzyl-4-chloroquinoline-3-carboxylate 
• 1177256-07-3 6-benzyl-4-benzyloxyquinoline-3-carboxylic acid ethyl ester 
• 1415907-45-7 6-benzyl-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate ethyl ester 

Relevant academic research and scientific papers

4-Quinolone derivatives: High-affinity ligands at the benzodiazepine site of brain GABAA receptors. Synthesis, pharmacology, and pharmacophore modeling

The 3-ethoxycarbonyl-4-quinolone compound 1 has previously been identified via a database search as an interesting lead compound for ligand binding at the benzodiazepine site of GABAA receptors (Kahnberg et al. J. Mol. Graphics Modelling 2004, 23, 253-261). Pharmacophore-guided optimization of this lead compound yielded a number of high-affinity ligands for the benzodiazepine site including compounds 20 and 23-25 displaying sub-nanomolar affinities. A few of the compounds have been tested on the α1β 2γ2S and α3β 2γ2S GABAA receptor subtypes, and two of the compounds (5 and 19) display selectivity for α1-versus α3-containing receptors by a factor of 22 and 27, respectively. This selectivity for α1β2γ2S is in the same range as that for the well-known α1 subunit selective compound zolpidem.

Green efficient synthesis method of quinolone compound

The invention discloses a green efficient synthesis method of a quinolone compound. The method is as follows: Step 1, a dicarbonyl compound, triethyl orthoformate and an aniline compound react in theabsence of a solvent and a catalyst to obtain an enamine ester intermediate; and Step 2, the enamine ester intermediate is subjected to an intramolecular cyclization reaction under the action of a cyclization reagent diphenyl ether to obtain a quinolone parent ring compound. The purity of the product reaches up to 98.8%. the synthesis method of the invention has the following main beneficial effects: 1, the reaction in the Step 1 is efficient, and no catalyst or solvent is used so as to avoid generation of the three wastes and the yield is high; 2, the process in the step 2 is green, the cyclization reagent can be recycled and reused; and 3, the process is simple, the steps 1 and 2 can be carried out in the same reactor, and the quinolone compound is obtained after reaction and filtration.

Investigating the role of metal chelation in HIV-1 integrase strand transfer inhibitors

HIV-1 integrase (IN) has been validated as an attractive target for the treatment of HIV/AIDS. Several studies have confirmed that the metal binding function is a crucial feature in many of the reported IN inhibitors. To provide new insights on the metal

Use of 2-[18F]fluoroethylazide for the Staudinger ligation - Preparation and characterisation of GABAA receptor binding 4-quinolones

The labelling reagent 2-[18F]fluoroethylazide was used in a traceless Staudinger ligation. This reaction was employed to obtain the GABAA receptor binding 6-benzyl-4-oxo-1,4-dihydro-quinoline-3- carboxylic acid (2-[18F]flu

Quinolone carboxylic acids as a novel monoketo acid class of human immunodeficiency virus type 1 integrase inhibitors

Human immunodeficiency virus type 1 (HIV-1) integrase is a crucial target for antiretroviral drugs, and several keto - enol acid class (often referred to as diketo acid class) inhibitors have clinically exhibited-marked antiretroviral activity. Here, we show the synthesis and the detailed structure - activity relationship of the quinolone carboxylic acids as a novel monoketo acid class of integrase inhibitors. 6-(3-Chloro-2-fluorobenzyl)-1-((2S)-1-hydroxy-3,3- dimethylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 51, which showed an IC50 of 5.8 nMin the strand transfer assay and an ED50 of 0.6 nMin the antiviral assay, and 6-(3-chloro-2-fluorobenzyl) -1-((2S)-1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3- carboxylic acid 49, which had an IC50 of 7.2 nMand an ED50 of 0.9 nM, were the most potent compounds in this class. The monoketo acid 49 was much more potent at inhibiting integrasecatalyzed strand transfer processes than 3′-processing reactions, as is the case with the keto - enol acids. Elvitegravir 49 was chosen as a candidate for further studies and is currently in phase 3 clinical trials.

IMAGING AGENTS

The invention relates to compounds of formula (I), or a salt or solvate thereof which comprise a detectable label. The compounds have use as radioligands for the GABAA receptor.

Novel HIV-1 integrase inhibitors derived from quinolone antibiotics

The viral enzyme integrase is essential for the replication of human immunodeficiency virus type 1 (HIV-1) and represents a remaining target for antiretroviral drugs. Here, we describe the modification of a quinolone antibiotic to produce the novel integr

Efflux pump inhibitors

Compounds are described which have efflux pump inhibitor activity. Also described are methods of using such efflux pump inhibitor compounds and pharmaceutical compositions which include such compounds.