19514-01-3

Upstream product

• 95-48-7 ortho-cresol 
• 70-11-1 α-bromoacetophenone 
• 4549-72-8 sodium o-cresolate 

Downstream Products

• 381730-35-4 3,5-diphenyl-6-o-tolyloxy-3,6-dihydro-[1,3,4]oxadiazin-2-one 
• 639011-08-8 (+)-(S)-2-(2-methylphenoxy)-1-phenylethanol 
• 1620831-57-3 1-phenyl-4-(phenylsulfonyl)-2-(o-tolyloxy)butan-1-one 
• 4202-12-4 1-phenylvinyl dimethyl phosphate 
• 1051392-63-2 (Z)-1-phenyl-2-o-tolyloxy-ethanone oxime 
• 42435-33-6 7-methyl-3-phenylbenzofuran 
• 50543-55-0 7-methyl-2-phenylbenzofuran 

Relevant academic research and scientific papers

Antiarrhythmic Hit to Lead Refinement in a Dish Using Patient-Derived iPSC Cardiomyocytes

Ventricular cardiac arrhythmia (VA) arises in acquired or congenital heart disease. Long QT syndrome type-3 (LQT3) is a congenital form of VA caused by cardiac sodium channel (INaL) SCN5A mutations that prolongs cardiac action potential (AP) and enhances INaL current. Mexiletine inhibits INaL and shortens the QT interval in LQT3 patients. Above therapeutic doses, mexiletine prolongs the cardiac AP. We explored structure-activity relationships (SAR) for AP shortening and prolongation using dynamic medicinal chemistry and AP kinetics in human-induced pluripotent stem cell-derived cardiomyocytes (hiPSC-CMs). Using patient-derived LQT3 and healthy hiPSC-CMs, we resolved distinct SAR for AP shortening and prolongation effects in mexiletine analogues and synthesized new analogues with enhanced potency and selectivity for INaL. This resulted in compounds with decreased AP prolongation effects, increased metabolic stability, increased INaL selectivity, and decreased avidity for the potassium channel. This study highlights using hiPSC-CMs to guide medicinal chemistry and "drug development in a dish".

Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent

Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.

Lewis-acid-mediated intramolecular trifluoromethylthiolation of alkenes with phenols: Access to SCF3-containing chromane and dihydrobenzofuran compounds

A Lewis-acid-mediated intramolecular trifluoromethylthiolation of alkenes with phenols that can offer direct access to SCF3-containing chromane and dihydrobenzofuran compounds was disclosed for the first time. Numerous SCF3-containing chromanes were obtai

Liquid chromatographic resolution of mexiletine and its analogs on crown ether-based chiral stationary phases

Mexiletine, an effective class IB antiarrhythmic agent, and its analogs were resolved on three different crown ether-based chiral stationary phases (CSPs), one (CSP 1) of which is based on (+)-(18-crown-6)-2,3,11,12- tetracarboxylic acid and the other two (CSP 2 and CSP 3) are based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6. Mexiletine was resolved with a resolution (RS) of greater than 1.00 on CSP 1 and CSP 3 containing residual silanol group-protecting n-octyl groups on the silica surface, but with a resolution (RS) of less than 1.00 on CSP 2. The chromatographic behaviors for the resolution of mexiletine analogs containing a substituted phenyl group at the chiral center on the three CSPs were quite dependent on the phenoxy group of analytes. Namely, mexiletine analogs containing 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3-methylphenoxy, 4-methylphenoxy, and a simple phenoxy group were resolved very well on the three CSPs even though the chiral recognition efficiencies vary with the CSPs. However, mexiletine analogs containing 2-methylphenoxy group were not resolved at all or only slightly resolved. Among the three CSPs, CSP 3 was found to show the highest chiral recognition efficiencies for the resolution of mexiletine and its analogs, especially in terms of resolution (RS). Chirality 26:272-278, 2014. 2014 Wiley Periodicals, Inc.

Novel one-pot synthesis of 3-Phenylnaphtho[2,3-b]furan and 3-phenylbenzofurans under microwave irradiation and solvent-free conditions

A one-pot synthesis of functionalized benzofurans has been developed via O-alkylation, carbon-carbon coupling/cyclization, and dehydration/olefination tandem reactions from phenacyl bromide and phenols under microwave irradiation and solvent-free conditio

A practical and efficient route for the highly enantioselective synthesis of mexiletine analogues and novel β-thiophenoxy and pyridyl ethers

(Chemical Equation Presented) A practical and efficient procedure for the enantioselective synthesis of mexiletine analogues with use of 10% of spiroborate ester 6 as chirality transfer agent is presented. A variety of mexiletine analogues were prepared in good yield with excellent enantioselectivities (91-97% ee) from readily available starting materials. The developed methodology was also successfully applied for the synthesis of novel β-amino ethers containing thiophenyl and pyridyl fragments.

Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents

An efficient combinatorial route to substituted 3-phenyl-benzofurans, is achieved by the bromination of acetophenones to α-bromoacetophenones by polymer-supported pyridinium bromide perbromide (PSPBP). The subsequent clean substitution of the obtained bromides by phenols using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD-P) and cyclodehydration of the resulting α-phenoxyacetophenones using Amberlyst 15, affords pure products without the need for any chromatographic purification step.

Anti-microbial alkyl substituted-2-nitro-3-phenylbenzofurans

Methyl-substituted-2-nitro-3-phenylbenzofurans are prepared from methyl-substituted-3-phenylbenzofurans and are found to be useful antimicrobial agents.