19359-22-9

Upstream product

• 101-92-8 4'-Chloroacetoacetanilide 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 115321-06-7 N-(4-chlorophenyl)-4,5-dihydro-4-oxo-2-[(4-chlorophenyl)amino]-3-furancarboxamide 

Relevant academic research and scientific papers

Creating novel activated factor XI inhibitors through fragment based lead generation and structure aided drug design

Activated factor XI (FXIa) inhibitors are anticipated to combine anticoagulant and profibrinolytic effects with a low bleeding risk. This motivated a structure aided fragment based lead generation campaign to create novel FXIa inhibitor leads. A virtual screen, based on docking experiments, was performed to generate a FXIa targeted fragment library for an NMR screen that resulted in the identification of fragments binding in the FXIa S1 binding pocket. The neutral 6-chloro-3,4-dihydro-1H-quinolin-2-one and the weakly basic quinolin-2-amine structures are novel FXIa P1 fragments. The expansion of these fragments towards the FXIa prime side binding sites was aided by solving the X-ray structures of reported FXIa inhibitors that we found to bind in the S1-S1'-S2' FXIa binding pockets. Combining the X-ray structure information from the identified S1 binding 6-chloro-3,4-dihydro-1H-quinolin-2-one fragment and the S1-S1'-S2' binding reference compounds enabled structure guided linking and expansion work to achieve one of the most potent and selective FXIa inhibitors reported to date, compound 13, with a FXIa IC50 of 1.0 nM. The hydrophilicity and large polar surface area of the potent S1-S1'-S2' binding FXIa inhibitors compromised permeability. Initial work to expand the 6-chloro-3,4-dihydro-1H-quinolin-2-one fragment towards the prime side to yield molecules with less hydrophilicity shows promise to afford potent, selective and orally bioavailable compounds.

Compound containing thiophene structure and application thereof in medicine

The present invention provides a compound of formula (I) and a pharmaceutically acceptable salt thereof, for use in the prevention and/or treatment of thromboembolic diseases and/or thromboembolic complications, wherein all variables are as defined in the specification.

Visible Light-Induced Pericyclic Cascade Reaction for the Synthesis of Quinolinone Derivatives with an Oxabicyclo[4.2.0]octene Skeleton

A photoinduced pericyclic cascade reaction has been developed to afford oxabicyclo[4.2.0]octenes. Mechanistic studies show that this reaction undergoes [2 + 2]-photocycloaddition, base-promoted elimination, retro-4π-electrocyclization, [1,5]-H shift, and

Click chemistry approach for the regioselective synthesis of iso-indoline-1,3-dione-linked 1,4 and 1,5 coumarinyl 1,2,3-triazoles and their photophysical properties

Copper-catalyzed reaction of N-propargyl isoindoline-1,3-dione and 4-azidomethyl coumarins / 4-azidomethyl-1-aza coumarins under click chemistry conditions afforded 1,4-disubstituted 1,2,3-triazoles, whereas ruthenium catalysis yielded isomeric 1,5-disubstituted 1,2,3-triazoles. The two regioisomers have been distinguished by NOE studies. UV absorption for a given pair of isomers exhibited similar trend, whereas fluorescence measurements showed considerable differences. Photo physical studies on the interaction of azides with copper and ruthenium have also been performed.

Synthesis and anti-bacterial evaluation of 4-aryloxymethyl carbostyrils derived from substructures and degradation products of Vancomycin

Vancomycin has been used as an antibiotic selectively against Gram-positive bacteria; however in the past decade they have grown resistant against it. The present work describes synthesis of a series of 4-aryloxymethyl carbostyrils derived from the reaction of 4-bromomethyl carbostryils with degradation products of Vancomycin (ethyl gallate and ethyl ester of N-benzoyl tyrosine ethyl ester). Further, gallate ethers 4a-d and tyrosine ethers 5a-d have been found to be selectively active against Gram-positive bacteria.

A new route for the synthesis of 4-arylacetamido-2-aminothiazoles and their biological evaluation

A series of 4-arylacetamido-2-amino- and 2-arylamino-1,3-thiazoles (4a-o) were synthesized in a single step in high yields from ?-bromoacetoacetanilides and thiourea/phenyl thioureas and were characterized by spectral and analytical methods. The compounds were evaluated for their in vitro antibacterial antifungal and antioxidant activities. In vitro antimicrobial evaluation of these compounds indicated their specificity towards Gram-positive species. p-Tolyl and m-chlorophenyl substituents on the arylamino moiety (compounds 4b and 4g) exhibited the lowest minimum inhibitory concentration values. The other compounds exhibited promising antimicrobial and moderate antioxidant activity.

Synthesis and biological activities of some new fluorinated coumarins and 1-aza coumarins

A series of new fluorinated coumarins and 1-aza coumarins have been synthesized and the presence of fluorine in these molecules and its effect on their anti-microbial, anti-inflammatory and analgesic activities are discussed. The results of bioassay showed that these newly synthesized compounds containing fluorine exhibit moderate analgesic and excellent anti-inflammatory and potential anti-bacterial and anti-fungal activities, compared to the other halogenated compounds. All the newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR, 13C NMR, 19F NMR, EI-MS, and FAB-MS. The ORTEP diagram of one of the compounds is reported herein.

Drug-induced modifications of the immune response. 12. 4,5-Dihydro-4-oxo-2-(substituted amino)-3-furancarboxylic acids and derivatives as novel antiallergic agents

The synthesis of a series of novel 4,5-dihydro-4-oxo-2-(substituted amino)-3-furancarboxylic acids, salts, esters, and amides is described. The title compounds when tested in the mediator-induced dermal vascular permeability and active anaphylaxis assays in rats demonstrated moderate to potent antiallergic activity. The [2-trans-(4-methyl-phenyl)cyclopropyl]amino analogue 53 emerged as the most active derivative. Thus, when administered intraperitoneally to rate at a dose of 100 mg/kg, it inhibited the action of the mediators serotonin, histamine, and bradykinin by 100%. In the active anaphylaxis assay in rats, compound 30 suppressed the edema by 81% at a dose of 100 mg/kg, following intraperitoneal administration.

Thiocyanation Reaction of Mercury(II) Complexes of Some Substituted Aromatic Acetoacetamides

Complexes of Hg(II) with acetoacetanilide (AAAH), acetoacet-ortho-toluidide (OAATH), 2,4-acetoacetxylidide (AAXH); 2,4-acetoacet-para-anisidide (PAAAH); acetoacet-para-chloroanilide (PCAAAH), ω-bromo-acetoacetanilide (ω-BrAAAH), ω-bromoacetoacet-ortho-tol