101860-74-6

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 7-chloro-
• Synonyms: 4H-1-Benzopyran-4-one, 7-chloro-
• CAS NO: 101860-74-6
• Molecular Formula: C₉H₅ClO₂
• Molecular Weight: 180.5878
• Mol File: 101860-74-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 7-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 7-chloro-(101860-74-6)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 7-chloro-(101860-74-6)

Safety Data

• Hazardous Substances Data: 101860-74-6(Hazardous Substances Data)

Upstream product

• 6921-66-0 4-chloro-2-hydroxy acetophenone 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 107826-00-6 7-Chloro-chromen-4-one oxime 
• 107825-94-5 5-Chloro-2-(5-methoxy-4,5-dihydro-isoxazol-3-yl)-phenol 
• 107825-99-0 7-Chloro-2-methoxy-chroman-4-one oxime 
• 107825-97-8 5-Chloro-2-isoxazol-5-yl-phenol 
• 84531-21-5 4-(5-Chloro-2-hydroxy-benzoyl)-1H-pyrrole-2-carboxylic acid ethyl ester 

Relevant articles and documents

NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenonesviaα,β-unsaturated acyl azoliums

A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenesviathe formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.

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).