936352-88-4

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 1131-80-2 (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one 
• 1253196-63-2 ethyl 2-benzoyl-3-(phenylamino)propenoate 
• 93-89-0 benzoic acid ethyl ester 
• 122-51-0 orthoformic acid triethyl ester 
• 62-53-3 aniline 
• 39973-76-7 ethyl 2-benzoyl-3-ethoxyacrylate 
• 1885-29-6 anthranilic acid nitrile 
• 31172-40-4 (E)-3-ethoxy-1-phenylprop-2-ene-1-one 

Downstream Products

• 142671-74-7 3-benzoyl-1-methyl-1H-quinolin-4-one 
• 127448-38-8 (4-chloroquinolin-3-yl)(phenyl)methanone 
• 936352-92-0 [4-(3-aminophenyl)quinolin-3-yl](phenyl)methanone 

Relevant academic research and scientific papers

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.

Synthesis and photochromism of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones

Synthesis and characterization of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones is described. In addition to their potential biological activity, these compounds exhibit photoreversible photochromic properties in anaerobic conditions. Using the 1 and 2D NMR techniques we demonstrated that the coloration occurred owing to the formation of fluorescent 5a,6-dihydrobenzo[b]acridin-(5H)-ones. The photoreaction is stereoselective and the S,R-isomers are the major products (83%) whereas the S,S-isomers are the minor (6%). In addition, the irreversible formation of two oxidation products, 3-(2-benzoylbenzoyl)quinolin-4(1H)-ones, and acridin-12(5H)-one derivatives was observed in the presence of air.

Further modification on phenyl acetic acid based quinolines as liver X receptor modulators

A series of phenyl acetic acid based quinolines was prepared as LXR modulators. An SAR study in which the C-3 and C-8 positions of the quinoline core were varied led to the identification of two potent LXR agonists 23 and 27. Both compounds displayed good binding affinity for LXRβ and LXRα, and increased expression of ABCA1 in THP-1 cells. These two compounds also had desirable pharmacokinetic profiles in mice and displayed in vivo efficacy in a 12-week Apo E knockout mouse lesion model.

Pharmacomodulations around the 4-oxo-1,4-dihydroquinoline-3-carboxamides, a class of potent CB2-selective cannabinoid receptor ligands: Consequences in receptor affinity and functionality

CB2 receptor selective ligands are becoming increasingly attractive drugs due to the potential role of this receptor in several physiopathological processes. Thus, the development of our previously described series of 4-oxo-1,4-dihydroquinoline-3-carboxamides was pursued with the aim to further characterize the structure-affinity and structure-functionality relationships of these derivatives. The influence of the side chain was investigated by synthesizing compounds bearing various carboxamido and keto substituents. On the other hand, the role of the quinoline central scaffold was studied by synthesizing several 6-, 7-, or 8-chloro-4-oxo-1,4-dihydroquinolines, as well as 4-oxo-1,4-dihydronaphthyridine and 4-oxo-1,4-dihydrocinnoline derivatives. The effect of these modifications on the affinity and functionality at the CB2 receptor was studied and allowed for the characterization of new selective CB2 receptor ligands.

Studies with Enaminones: The reaction of enaminones with Aminoheterocycles. A route to Azolopyrimidines, Azolopyridines and Quinolines

The enaminones 1b,d,f react with 4-phenyl-3-methyl-5-pyrazoleamine 3a to yield the pyrazole derivatives 4a-c that cyclised readily on reflux in pyridine solution in presence of hydrochloric acid to yield the pyrazolo[1,5-a]pyrimidines 5a-c. Similarly 3(5)

A versatile and efficient synthesis of 3-aroyl-1,4-dihydroquinolin-4-ones

A versatile and efficient method for preparation of 3-aroyl-4-quinolones is described. The procedure involved a Michael-type addition of methyl anthranylate with various β-ketonic enol ethers followed by based promoted cyclisation. Different quinolones have been obtained. The ring closure is facilitated by heating at reflux in diphenyl ether leading to increase the rate of the cyclisation.