5751-51-9

Upstream product

• 102539-54-8 3-bromo-7-methyl-chroman-4-one 
• 6921-64-8 4'-hydroxy-2'-methylacetophenone 
• 109-94-4 formic acid ethyl ester 
• 18385-69-8 7-methylchroman-4-one 
• 180596-06-9 5-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-4H-1-benzopyran-4-one 
• 76-26-6 camphor-10-sulfonic acid 
• 52103-12-5 3-iodopropyl tetrahydro-2H-pyran-2-yl ether 
• 865352-25-6 C₁₂H₁₅NO₂ 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 25173-36-8 3-(3-methylphenoxy)propionic acid 
• 175853-71-1 7-Methyl-4-oxo-chroman-3-carbaldehyde 

Downstream Products

• 21172-20-3 4-(3-ethyl-6-methyl-3H-benzothiazol-2-ylidenemethyl)-7-methyl-chromenylium; 2-nitro-benzenesulfonate 
• 21172-19-0 4-(3-ethyl-3H-benzothiazol-2-ylidenemethyl)-7-methyl-chromenylium; 2-nitro-benzenesulfonate 
• 164171-56-6 5-(2-hydroxy-4-methylphenyl)isoxazole 
• 331683-65-9 7-(bromomethyl)-4H-benzopyran-4-one 
• 84531-13-5 Ethyl 4-(2-hydroxy-5-methylbenzoyl)-1H-pyrrole-2-carboxylate 
• 21301-50-8 2-{2-(2-acetoxy-4-methyl-phenyl)-5-[3-(3-ethyl-6-methyl-3H-benzothiazol-2-ylidenemethyl)-5,5-dimethyl-cyclohex-2-enylidene]-penta-1,3-dienyl}-3-ethyl-6-methyl-benzothiazolium; iodide 

Relevant academic research and scientific papers

Ruthenium(II)-Catalyzed C-H Activation of Chromones with Maleimides to Synthesize Succinimide/Maleimide-Containing Chromones

An efficient route for the coupling of maleimides with chromones at the C5-position has been developed under Ru(II) catalysis. It could provide 1,4-addition products and oxidative Heck-type products by switching additives. Benzoic acid led to the formation of 1,4-addition products under solvent-free conditions, and silver acetate was promoted to the generation of oxidative Heck-type products. Various maleimides and chromones were suitable for this transformation, affording the desired products with good to excellent yields in a short reaction time. To understand the mechanism of this reaction, deuteration studies and control experiments have been performed.

Direct Enantio- and Diastereoselective Vinylogous Addition of Butenolides to Chromones Catalyzed by Zn-ProPhenol

We report the first enantio- and diastereoselective 1,4-addition of butenolides to chromones. Both α,β- and β,γ-butenolide nucleophiles are compatible with the Zn-ProPhenol catalyst, and preactivation as the siloxyfurans is not required. The scope of electrophiles includes a variety of substituted chromones, as well as a thiochromone and a quinolone, and the resulting vinylogous addition products are generated in good yield (31 to 98%), diastereo- (3:1 to >30:1), and enantioselectivity (90:10 to 99:1 er). These Michael adducts allow rapid access to several natural product analogs, and can be easily transformed into a variety of other interesting scaffolds as well.

Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides

A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.

Substituent-Oriented Synthesis of Substituted Pyrazoles/Chromeno[3,2- c]pyrazoles via Sequential Reactions of Chromones/3-Chlorochromones and Tosylhydrazones

A facile and efficient synthetic strategy for the chemoselective synthesis of monocyclic/tricyclic-fused pyrazoles was developed, and it was oriented by different 3-position substituents (H or Cl) on the chromones. The reaction proceeded in a one-pot sequential way with a broad substrate scope and moderate to excellent yields.

Discovery of 4-[(2R,4R)-4-({[1-(2,2-Difluoro-1,3-benzodioxol-5-yl)cyclopropyl]carbonyl}amino)-7-(difluoromethoxy)-3,4-dihydro-2H-chromen-2-yl]benzoic Acid (ABBV/GLPG-2222), a Potent Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) Corrector for the Treatment of Cystic Fibrosis

Cystic fibrosis (CF) is a multiorgan disease of the lungs, sinuses, pancreas, and gastrointestinal tract that is caused by a dysfunction or deficiency of the cystic fibrosis transmembrane conductance regulator (CFTR) protein, an epithelial anion channel that regulates salt and water balance in the tissues in which it is expressed. To effectively treat the most prevalent patient population (F508del mutation), two biomolecular modulators are required: correctors to increase CFTR levels at the cell surface, and potentiators to allow the effective opening of the CFTR channel. Despite approved potentiator and potentiator/corrector combination therapies, there remains a high need to develop more potent and efficacious correctors. Herein, we disclose the discovery of a highly potent series of CFTR correctors and the structure-activity relationship (SAR) studies that guided the discovery of ABBV/GLPG-2222 (22), which is currently in clinical trials in patients harboring the F508del CFTR mutation on at least one allele.

SUBSTITUTED CHROMANES AND METHOD OF USE

The invention provides for compounds of formula (I), wherein R1, X, Y, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, m, and R" have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents in the treatment of diseases and conditions mediated and modulated by CFTR, including cystic fibrosis, Sj?gren's syndrome, pancreatic insufficiency, chronic obstructive lung disease, and chronic obstructive airway disease. Also provided are pharmaceutical compositions comprised of one or more compounds of formula (I).

Lewis Acid-catalysed Facile Elimination of the Diazo Group in 3-Diazochromanones. Novel Conversion of Chromanones into Chromones

3-Diazochromanones undergo rapid elimination of the diazo group in presence of BF3- Et2O to furnish chromones.

5-aminoflavone derivatives

5-Aminoflavone derivatives represented by the formula (I): STR1 wherein R1, R2, R3 and R4 are the same or different and represent hydrogen, substituted or unsubstituted lower alkyl, lower alkenyl, halogen-substi

5-Aminoflavone derivatives, their preparation and their use as antibacterial, anti-estrogenic and/or antitumor agent

5-Aminoflavone derivatives represented by the formula (I): wherein R1 and R2 are the same or different and represent hydrogen or substituted or unsubstituted lower alkyl, X represents substituted or unsubstituted lower alkyl, lower alkenyl, lower alkynyl,

Potent Inhibitors of Acyl-CoA:Cholesterol Acyltransferase. Structure-Activity Relationships of Novel N-(4-Oxochroman-8-yl)amides

Novel N-(4-oxochroman-8-yl)amide derivatives 1 were synthesized and tested for their ability to inhibit rabbit small intestinal ACAT (acyl-CoA:cholesterol acyltransferase) in vitro and to lower serum total cholesterol in cholesterol-fed rats in vivo.Among the synthesized compounds, N-(7-alkoxy-4-oxochroman-8-yl)amide derivatives showed potent ACAT inhibitory activity both in vitro and in vivo.The structure-activity relationships of these N-(4-oxochroman-8-yl)amides and related compounds are discussed on the basis of these two assays.The carbonyl group at position 4 of the 4-chromanone was essential for potent ACAT inhibitory activity.N-(Chromon-8-yl) derivatives were less potent than N-(4-oxochroman-8-yl) derivatives.An alkoxy group at position 7 of the 4-chromanone moiety was important for potent ACAT inhibitory activity.In the N-(7-alkoxy-4-oxochroman-8-yl)amide derivatives, another necessary factor to elicit the potent ACAT inhibitory activity was lipophilicity of the molecules.The highly lipophilic acid amides N-(7-methoxy-4-oxochroman-8-yl)-2,2-dimethyldodecanamide (35) and 4-oxy>-N-(7-methoxy-4-oxochroman-8-yl)benzamide (63) showed potent activity.Introduction of a highly lipophilic alkoxy group at position 7 of the 4-chromanone moiety instead of methoxy group also resulted in potent activity.In this case, highest inhibitory activity was obtained by N--2,2-dimethylpropanamide (65).The most potent compound, N-(7-methoxy-4-oxochroman-8-yl)-2,2-dimethyldodecanamide (35, TEI-6522), showed significant ACAT inhibitory activity (rabbit small intestine IC50 = 13 nM, rabbit liver IC50 = 16 nM), foam cell formation inhibitory activity (rat peritoneal macrophage IC50 = 160 nM), and extremely potent serum cholesterol-lowering activity in cholesterol-fed rats (61percent at a dose of 0.1 mg/kg/day po).