Synthesis and evaluation of sulfonamide derivatives as potent Human Uric Acid Transporter 1 (hURAT1) inhibitors

Yang, Xintuo; Pang, Xiaobing; Fan, Lei; Li, Xinghai; Chen, Yuanwei

doi:10.1016/j.bmcl.2017.03.041

Cited by 1 publication

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“…The derivative of triflamide 126 is known to exhibit biological activity and act as an inhibitor of the transporter derivatives of uric acid (hURAT1). In medicine, there are only three options for drugs of this kind, although they are extremely necessary in the treatment of hyperuricemia, which subsequently causes many diseases, such as gout, arterial hypertension, chronic kidney disease and some cardiovascular diseases [136] Triflamide compound 126 was synthesized by following Scheme 35. Bis(pinacolato)diboron reacted with 122 under the catalyst of Pd(dppf)Cl 2 , which gave compound 123.…”

Section: Synthesis Of Biologically Active Triflamide Derivativesmentioning

confidence: 99%

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Triflamides and Triflimides: Synthesis and Applications

Moskalik

Astakhova

2022

Molecules

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Among the variety of sulfonamides, triflamides (CF3SO2NHR, TfNHR) occupy a special position in organic chemistry. Triflamides are widely used as reagents, efficient catalysts or additives in numerous reactions. The reasons for the widespread use of these compounds are their high NH-acidity, lipophilicity, catalytic activity and specific chemical properties. Their strong electron-withdrawing properties and low nucleophilicity, combined with their high NH-acidity, makes it possible to use triflamides in a vast variety of organic reactions. This review is devoted to the synthesis and use of N-trifluoromethanesulfonyl derivatives in organic chemistry, medicine, biochemistry, catalysis and agriculture. Part of the work is a review of areas and examples of the use of bis(trifluoromethanesulfonyl)imide (triflimide, (CF3SO2)2NH, Tf2NH). Being one of the strongest NH-acids, triflimide, and especially its salts, are widely used as catalysts in cycloaddition reactions, Friedel–Crafts reactions, condensation reactions, heterocyclization and many others. Triflamides act as a source of nitrogen in C-amination (sulfonamidation) reactions, the products of which are useful building blocks in organic synthesis, catalysts and ligands in metal complex catalysis, and have found applications in medicine. The addition reactions of triflamide in the presence of oxidizing agents to alkenes and dienes are considered separately.

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Section: Synthesis Of Biologically Active Triflamide Derivativesmentioning

confidence: 99%

“…Bis(pinacolato)diboron reacted with 122 under the catalyst of Pd(dppf)Cl 2 , which gave compound 123. Further Suzuki coupling of 123 with 4-amino-3-bromopyridine 124 provided 125, which subsequently reacted with CF 3 SO 2 Cl under the conditions of Et 3 N in DCM to afford compound 126 [136].…”

Section: Synthesis Of Biologically Active Triflamide Derivativesmentioning

confidence: 99%

Triflamides and Triflimides: Synthesis and Applications

Moskalik

Astakhova

2022

Molecules

View full text Add to dashboard Cite

show abstract

Synthesis and evaluation of sulfonamide derivatives as potent Human Uric Acid Transporter 1 (hURAT1) inhibitors

Cited by 1 publication

References 15 publications

Triflamides and Triflimides: Synthesis and Applications

Triflamides and Triflimides: Synthesis and Applications

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