An Efficient Strategy for the Synthesis of 1-(Trifluoromethylsulfonamido)propan-2-yl Esters and the Evaluation of Their Cytotoxic Activity

Gómez-García, Omar; Gómez, Elizabeth; Monzón-González, César; Ramírez‐Ápan, Teresa; Álvarez-Toledano, Cecilio

doi:10.1248/cpb.c16-00724

Cited by 4 publications

(6 citation statements)

References 39 publications

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“…The reaction of 5-methyl-2-phenyl-4,5-dihydrooxazole 76 with trifluoromethanesulfonic acid anhydride 77 leads to the formation of trifluoromethanesulfonamido)prop-2-yl esters of phenyl-substituted derivatives of benzoic acid 78 [122] P450-catalysed arene hydroxylation is accepted to occur via an NIH-shift within an iminium intermediate to give a dienone that re-aromatizes to phenol [121]. Biocatalytic hydroxylation reactions are used for the synthesis of drugs, agrochemicals and their metabolites.…”

Section: Synthesis Of Biologically Active Triflamide Derivativesmentioning

confidence: 99%

“…The reaction of 5-methyl-2-phenyl-4,5-dihydrooxazole 76 with trifluoromethanesulfonic acid anhydride 77 leads to the formation of trifluoromethanesulfonamido)prop-2-yl esters of phenyl-substituted derivatives of benzoic acid 78 [122] (Scheme 23): Scheme 23. Ring-opening of the 5-methyl-2-phenyl-4,5-dihydrooxazole system by triflic anhydride.…”

Section: Synthesis Of Biologically Active Triflamide Derivativesmentioning

confidence: 99%

“…The reaction does not require the presence of bases. Derivatives with R = 4-Cl, 4-NO 2 and 4-CF 3 show high cytotoxicity against six human cancer cell lines (U251 (glioblastoma), PC-3 (prostate adenocarcinoma), K-562 (chronic myelogenous leukemia), HCT-15 (colorectal adenocarcinoma), MCF-7 (breast adenocarcinoma), SKLU-1 (lung adenocarcinoma) and the 4-CF 3 derivative was active against human gum cancer cells (FGH (gingival fibroblastoma) [122].…”

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%

“…The reaction of 5-methyl-2-phenyl-4,5-dihydrooxazole 76 with trifluoromethanesulfonic acid anhydride 77 leads to the formation of trifluoromethanesulfonamido)prop-2-yl esters of phenyl-substituted derivatives of benzoic acid 78 [122] (Scheme 23): Scheme 23. Ring-opening of the 5-methyl-2-phenyl-4,5-dihydrooxazole system by triflic anhydride.…”

Section: Synthesis Of Biologically Active Triflamide Derivativesmentioning

confidence: 99%

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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“…Accordingly, a concentration-response curve was constructed for each of the 2-amino-3-cyano-4H-chromenes 4a-o and 6a-h, and the values corresponding to an inhibition of 50% (IC 50 ) were calculated from non-linear regression equations. IC 50 values are expressed as the mean ± standard error (SE) [66].…”

Section: Cytotoxicity Assaymentioning

confidence: 99%

“…culated from non-linear regression equations. IC50 values are expressed as the mean ± standard error (SE) [66].…”

Section: Chemistrymentioning

confidence: 99%

Three-Component Synthesis of 2-Amino-3-cyano-4H-chromenes, In Silico Analysis of Their Pharmacological Profile, and In Vitro Anticancer and Antifungal Testing

et al. 2021

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Chromenes are compounds that may be useful for inhibiting topoisomerase and cytochrome, enzymes involved in the growth of cancer and fungal cells, respectively. The aim of this study was to synthesize a series of some novel 2-amino-3-cyano-4-aryl-6,7-methylendioxy-4H-chromenes 4a–o and 2-amino-3-cyano-5,7-dimethoxy-4-aryl-4H-chromenes 6a–h by a three-component reaction, and test these derivatives for anticancer and antifungal activity. Compounds 4a and 4b were more active than cisplatin (9) and topotecan (7) in SK-LU-1 cells, and more active than 9 in PC-3 cells. An evaluation was also made of the series of compounds 4 and 6 as potential antifungal agents against six Candida strains, finding their MIC50 to be less than or equal to that of fluconazole (8). Molecular docking studies are herein reported, for the interaction of 4 and 6 with topoisomerase IB and the active site of CYP51 of Candida spp. Compounds 4a–o and 6a–h interacted in a similar way as 7 with key amino acids of the active site of topoisomerase IB and showed better binding energy than 8 at the active site of CYP51. Hence, 4a–o and 6a–h are good candidates for further research, having demonstrated their dual inhibition of enzymes that participate in the growth of cancer and fungal cells.

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