784-39-4

Upstream product

• 106-47-8 4-chloro-aniline 
• 1711-07-5 3-fluorobenzoyl chloride 
• 1073-06-9 3-fluorobromobenzene 
• 635-21-2 5-chloroanthranilic acid 
• 150879-48-4 N-methyl-N-methyloxy-2-amino-5-chlorobenzamide 
• 4743-17-3 5-Chloroisatoic anhydride 
• 1537216-75-3 [5-chloro-2-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl](3-fluorophenyl)methanone 

Downstream Products

• 1449372-94-4 3-acetyl-6-chloro-4-(3-fluorophenyl)quinolin-2(1H)-one 
• 1449373-75-4 6-chloro-3-[5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]-4-(3-fluorophenyl)quinolin-2(1H)-one 
• 1449374-21-3 4-{3-[6-chloro-4-(3-fluorophenyl)-2-oxo-1,2-dihydroquinolin-3-yl]-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl}-4-oxobutanoic acid 
• 1449373-30-1 (E)-6-chloro-3-[3-(4-chlorophenyl)acryloyl]-4-(3-fluorophenyl)quinolin-2(1H)-one 
• 1332672-72-6 C₁₅H₁₁ClFNO₂ 
• 1332662-65-3 (RS)-6-chloro-4-(3-fluorophenyl)-2-methyl-3-(2-(piperidin-1-yl)ethyl)-3,4-dihydroquinazoline 
• 1332673-32-1 C₂₂H₂₅ClFN₃O 

Relevant academic research and scientific papers

One-Pot Synthesis of 2-Aminobenzophenones from 2-Alkynyl Arylazides Catalyzed by Pd and Cu Precursors

We describe a novel one-pot three-step reaction of 2-alkynyl arylazides through palladium-catalyzed formation of 3-hydroxy-3-phenylindolin-2-ones followed by hydrolysis of amide bonds and copper-catalyzed decarboxylation to give 2-aminobenzophenones. This synthetic method works well with various 2-alkynyl arylazides and affords the products in moderate to good yields under mild reaction conditions.

Trifluoroacetic acid: An efficient catalyst for paal-knorr pyrrole synthesis and its deprotection

In the present work, we demonstrated a simple and an efficient method for the condensation of substituted aryl/heteroaryl amines with acetonylacetone in the presence of trifluoro acetic acid to afford the corresponding 2,5-dimethyl-1-substitued pyrroles using Paal-Knorr synthesis in excellent yields. Trifluoroacetic acid was used under reflux condition for the deprotection of 2,5-dimethyl-1-substitued pyrroles to their corresponding substituted aryl/heteroaryl amines in moderate yields. 2,5-Dimethyl-1-substitued pyrrole were characterized by NMR and LC-MS. The yield of the compounds was found to be excellent.

Structure-activity relationships and pharmacophore model of a noncompetitive pyrazoline containing class of GluN2C/GluN2D selective antagonists

Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC 50 of 0.17-0.22 μM at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.

Synthesis of 2-aminobenzophenone derivatives and their anticancer activity

A number of 2-aminobenzophenones have been synthesized by acylation of para-chloroaniline with different 2-, 3-, 4-chloro-or fluorobenzoyl chloride in solid state via the Friedel-Crafts reaction. Synthesized compounds were characterized by 1H and 13C NMR, Fourier transform-infrared, ultraviolet-visible spectroscopy, mass spectrometry, and elemental analysis. Evaluation of biological activity in vitro showed that the selected compounds 9, 10, and 13 have potential anticancer activity. The presence of one chlorine atom in the second aromatic ring of the benzophenone molecule makes it more active.

Dihydroquinazolines as a novel class of Trypanosoma brucei trypanothione reductase inhibitors: Discovery, synthesis, and characterization of their binding mode by protein crystallography

Trypanothione reductase (TryR) is a genetically validated drug target in the parasite Trypanosoma brucei, the causative agent of human African trypanosomiasis. Here we report the discovery, synthesis, and development of a novel series of TryR inhibitors based on a 3,4-dihydroquinazoline scaffold. In addition, a high resolution crystal structure of TryR, alone and in complex with substrates and inhibitors from this series, is presented. This represents the first report of a high resolution complex between a noncovalent ligand and this enzyme. Structural studies revealed that upon ligand binding the enzyme undergoes a conformational change to create a new subpocket which is occupied by an aryl group on the ligand. Therefore, the inhibitor, in effect, creates its own small binding pocket within the otherwise large, solvent exposed active site. The TryR-ligand structure was subsequently used to guide the synthesis of inhibitors, including analogues that challenged the induced subpocket. This resulted in the development of inhibitors with improved potency against both TryR and T. brucei parasites in a whole cell assay.