68298-46-4

Usage

Uses

Used in Pharmaceutical Research:
2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-AMINE is used as a chemical entity in pharmaceutical research for its potential biological and pharmacological activities. Its unique molecular structure may contribute to the development of new drugs and therapies.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-AMINE is utilized as a compound with the potential to be modified and optimized for specific medical applications. Its amine functionality and benzofuran ring system provide a foundation for further chemical modifications to enhance its pharmacological properties.

InChI:InChI=1/C10H13NO/c1-10(2)6-7-4-3-5-8(11)9(7)12-10/h3-5H,6,11H2,1-2H3

Upstream product

• 13414-55-6 2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran 
• 1271665-78-1 2-(2,3-dihydro-2,2-dimethylbenzofuran-7-yloxy)propanamide 
• 846037-43-2 (2,2-dimethyl-2,3-dihydro-benzofuran-7-yl)-carbamic acid tert-butyl ester 

Downstream Products

• 87254-52-2 2,3-dihydro-2,2-dimethyl-7-benzofuransulfonyl chloride 
• 10178-57-1 7-bromo-2,3-dihydro-2,2-dimethylbenzofuran 

Relevant academic research and scientific papers

Metal-free C-N bond-forming reaction: Straightforward synthesis of anilines, through cleavage of aryl C-O bond and amide C-N bond

An efficient metal-free C-N bond forming reaction through cleavage of aryl C-O bond and amide C-N bond has been developed. This process represents a practical method for the facile construction of anilines with a broad substrate scope and wide functional group tolerance in moderate to excellent yields.

[1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia

This invention relates to compounds of the formula 1 wherein G, D, A, Z, Q, X, Y, R1, and R4 through R7 are defined as in the specification, processes for preparing the same and intermediates used in making the same, and pharmaceutical compositions containing such compounds and their use in the treatment of central nervous system disorders and other disorders.

Potent inhibitors of Acyl-CoA:cholesterol acyltransferase. 2. Structure- activity relationships of novel N-(2,2-dimethyl-2,3-dihydrobenzofuran-7- yl)amides

Novel N-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)amide derivatives 1 were synthesized and tested for their ability to inhibit rabbit small intestinal ACAT (acyl-CoA:cholesterol acyltransferase) and lower serum total cholesterol in cholesterol-fed rats. Among the synthesized compounds, N-(2,2,4,6- tetramethyl-2,3-dihydrobenzofuran-7-yl)amide derivatives showed potent ACAT inhibitory activity. The synthesis and structure-activity relationships of these compounds are described. A methyl group at position 6 of the 2,3- dihydrobenzofuran moiety was important for potent ACAT inhibitory activity. In the series of N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)amides, lipophilicity of the acyl moiety was necessary for the potent ACAT inhibitory activity. The highly lipophilic acid amides N-(2,2,4,6-tetramethyl-2,3- dihydrobenzofuran-7-yl)-2,2-dimethyldodecanamide (10) and 6-(4- chlorophenoxy)-N-(2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl)-2,2- dimethyloctanamide (50) showed potent activity. Introduction of a dimethylamino group at position 5 of the 2,3-dihydrobenzofuran moiety resulted in highly potent activity. The most potent compound, N-[5- (dimethylamino)-2,2,4,6-tetramethyl-2,3-dihydrobenzofuran-7-yl]-2,2- dimethyldodecanamide (13, TEI-6620), showed highly potent ACAT inhibitory activity (rabbit small intestine IC50 = 0.020 μM, rabbit liver IC50 = 0.009 μM), foam cell formation inhibitory activity (rat peritoneal macrophage IC50 = 0.030 μM), extremely potent serum cholesterol-lowering activity in cholesterol-fed rats (71% at a dose of 0.3 mg/kg/day po), and good bioavailability in fed dogs (C(max) = 2.68 μg/mL at 1 h, 10 mg/kg po).