6630-24-6

Usage

Chemical compound

2H-1-Benzopyran-6-carboxylic acid, 3,4-dihydro-2,2-diMethyl-, ethyl ester

Classification

Benzopyran derivative

Structure

Ethyl ester of 3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carboxylic acid

Uses

Widely used in pharmaceutical industry for drug synthesis and organic synthesis

Properties

Antioxidant and anti-inflammatory

Applications

Potential therapeutic use, fragrance, and flavoring agent

InChI:InChI=1/C14H18O3/c1-4-16-13(15)11-5-6-12-10(9-11)7-8-14(2,3)17-12/h5-6,9H,4,7-8H2,1-3H3

Upstream product

• 120-47-8 Ethyl 4-hydroxybenzoate 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 2039-47-6 2,2-dimethylchroman-6-carboxylic acid 
• 1740-74-5 1,1-diethoxy-3-methyl-2-butene 
• 32333-31-6 2,2-dimethyl-6-acetylchroman 
• 4167-73-1 4-(2-hydroxyphenyl)-2-methyl-2-butanol 
• 1198-96-5 2,2-dimethylchroman 
• 89091-82-7 4-(3-methyl-but-2-enyloxy)-benzoic acid ethyl ester 
• 64-17-5 ethanol 

Downstream Products

• 1442439-45-3 ethyl 4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl]carbonyl]amino]benzoate 
• 1442439-46-4 4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl]carbonyl]amino]benzoic acid 
• 192762-73-5 ethyl 2-fluoro-4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)-6-chromanyl]carbonyl]amino]benzoate 
• 192762-71-3 ethyl 8-bomo-2,2-dimethyl-4-(4-methylphenyl)-4(2H)-chroman-6-carboxylate 
• 192762-72-4 8-bromo-2,2-dimethyl-4-(4-methylphenyl)-4(2H)-chroman-6-carboxylic acid 

Relevant academic research and scientific papers

RAR-ALPHA COMPOUNDS FOR INFLAMMATORY DISEASE AND MALE CONTRACEPTION

Modulators of retinoid acid receptor-alpha (RARα) of formula (I) are provided herein, as well as pharmaceutical compositions and methods relating thereto.

Practical synthesis of a chromene analog for use as a retinoic acid receptor alpha antagonist lead compound

Retinoic acid receptor alpha (RARα) selective compounds may guide the design of drugs that can be used in conjunction with hormonal adjuvant therapy in the treatment of breast cancer. Herein we report a modified synthesis of a known RARα antagonist, 2-fluoro-4-[[[8-bromo-2,2-dimethyl-4-(4- methylphenyl)chroman-6-yl]carbonyl]amino]benzoic acid and a synthesis of its unknown, desfluoro analog, 4-[[[8-bromo-2,2-dimethyl-4-(4-methylphenyl)chroman- 6-yl]carbonyl]amino]benzoic acid. The modified route allows for facile reaction workups, increased yields, lower cost and incorporates a green alternative step. Structure-activity relationship studies determined through functional cell-based assays, demonstrated antagonism to RARα for both compounds. Molecular modeling within the RARα binding pocket was used to compare binding interactions of the desfluoro analog to a known RAR antagonist.

InIII-catalysed tandem C-C and C-O bond formation between phenols and allylic acetates

Indium triflate catalysed tandem allylation-intramolecular hydroalkoxylation was efficiently carried out by using 1 mol-% of the catalyst under mild conditions to afford the dihydrobenzopyran ring system (chroman-type structure) in good yields. Kinetic, mechanistic and theoretical studies are also presented. Tandem allylation-intramolecular hydroalkoxylation carried out in the presence of an indium catalyst (1 mol-%) under mild conditions provides the dihydrobenzopyranring system in good yields. Kinetic, mechanistic and theoretical studies are presented.

Bismuth triflate catalyzed [1,3] rearrangement of aryl 3-methylbut-2-enyl ethers

An efficient bismuth triflate catalyzed [1,3] rearrangement of aryl 3-methylbut-2-enyl ethers has been developed. The reaction proceeds rapidly and affords the corresponding para- and ortho-prenylated phenols and naphthols in moderate to good yields (up t

Identification of highly potent retinoic acid receptor α-selective antagonists

The syntheses and full retinoid receptor characterization of a novel series of retinoic acid receptor α (RARα) antagonists, 1-5, are described. These compounds bind with high affinity to RARα but were completely inactive in gene transactivation. They were also potent and effective antagonists of retinoic acid (RA) induced gene transcription at RARα. Compounds 1-5 exhibited varying degrees of selectivity for RARα relative to RARβ/γ, with compound 5 being the most selective in both binding and functional antagonism assays. These compounds will be invaluable tools in delineating the physiological roles of RARα in development and in the adult animal and may themselves be useful therapeutic agents in human diseases associated with RARα.