Trifluoroacetylation of amines and amino acids by polymer-bound trifluoroacetylation reagents

Svirskaya, P. I.; Leznoff, Clifford C.; Steinman, M.

doi:10.1021/jo00383a042

Cited by 28 publications

(9 citation statements)

References 3 publications

(3 reference statements)

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“…2). The identification of the compound was confirmed by IR, 1 H NMR, 13 C NMR and crystallography data as well as comparison with the data reported in the literature (Svirskaya and Leznoff 1987). In this communication, we report the antimicrobial, antioxidant, cytotoxicity and molecular docking properties of this compound.…”

Section: Resultssupporting

confidence: 74%

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Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

Balachandran¹,

Kumar²,

Arun

et al. 2014

Appl Nanosci

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N-Benzyl-2,2,2-trifluoroacetamide was obtained by acylation of benzylamine with trifluoroacetic anhydride using Friedel-Crafts acylation method. The synthesised compound was confirmed by spectroscopic and crystallographic techniques. N-Benzyl-2,2,2-trifluoroacetamide was assessed for its antimicrobial, antioxidant, cytotoxic and molecular docking properties. It showed good antifungal activity against tested fungi and moderate antibacterial activity. The minimum inhibitory concentration values of Nbenzyl-2,2,2-trifluoroacetamide against fungi were 15.62 lg/ mL against A. flavus, 31.25 lg/mL against B. Cinerea and 62.5 lg/mL against T. mentagrophytes, Scopulariopsis sp., C. albicans and M. pachydermatis. N-Benzyl-2,2,2-trifluoroacetamide showed 78.97 ± 2.24 of antioxidant activity at 1,000 lg/mL. Cupric ion reducing antioxidant capacity of N-benzyl-2,2,2-trifluoroacetamide was dependent on the concentration. Ferric reducing antioxidant power assay of N-benzyl-2,2,2-trifluoroacetamide showed (1.352 ± 0.04 mM Fe(II)/g) twofold higher value compared to the standard. N-Benzyl-2,2,2-trifluoroacetamide showed 75.3 % cytotoxic activity at the dose of 200 lg/mL with IC 50 (54.7 %) value of 100 lg/mL. N-Benzyl-2,2,2-trifluoroacetamide was subjected to molecular docking studies for the inhibition AmpC beta-lactamase, Glucosamine-6-Phosphate Synthase and lanosterol 14 alpha-demethylase (CYP51) enzymes which are targets for antibacterial and antifungal drugs. Docking studies of N-benzyl-2,2,2-trifluoroacetamide showed low docking energy. N-Benzyl-2,2,2-trifluoroacetamide can be evaluated further for drug development.

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Section: Resultssupporting

confidence: 74%

“…1). The synthesis of the compound has been reported using polymer-based Sbenzyl triflurothioacetate (Svirskaya and Leznoff 1987).…”

Section: Methodsmentioning

confidence: 99%

Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

Balachandran¹,

Kumar²,

Arun

et al. 2014

Appl Nanosci

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“…101 The reagents are prepared by reaction of trifluoroacetic anhydride with the polymer-bound benzyl thioalcohol or benzyl alcohol, respectively. Reaction with amines or amino acids results in the trifluoroacetate in high yields with no racemization of the chiral centers.…”

Section: • Drewry Coe and Poonmentioning

confidence: 99%

“…Trifluoroacetylation of amines and amino acids has been reported using a polymer-bound S-benzyl trifluorothioacetate or benzyl trifluoroacetate. 101 The reagents are prepared by reaction of trifluoroacetic anhydride with the polymer-bound benzyl thioalcohol or benzyl alcohol, respectively. Reaction with amines or amino acids results in the trifluoroacetate in high yields with no racemization of the chiral centers.…”

Section: P R O T E C T I O N a N D D E P R O T E C T I O N U S I N G P O L Y M E R -S U P P O R T E D R E A G E N T Smentioning

confidence: 99%

Solid-supported reagents in organic synthesis

Drewry¹,

Coe²,

Poon³

1999

Med. Res. Rev.

139

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The current interest in solid-phase organic synthesis has led to a renewed interest in a complementary technique in which solid supported reagents are used in solution phase chemistry. This technique obviates the need for attachment of the substrate to a solid-support, and enables the chemist to monitor the reactions using familiar analytical techniques. The purpose of this review is to increase awareness of the wide range of useful transformations which can be accomplished using solid-supported reagents.

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“…[14] The use of basic poly-TBD 2 allows for the rapid synthesis of aryl triflates (Scheme 3). [16] Finally, polymer-supported oxime 8 has served as a reagent for trapping primary amines after treatment with phosgene [17] to furnish intermediate oxime carbamates 9 (Scheme 4). This resin was treated with 4-nitrophenyl triflate which plays the role of a triflate transfer reagent thereby releasing the desired aryltriflate into solution.…”

Section: Introductionmentioning

confidence: 99%

The “Resin-Capture-Release” Hybrid Technique: A Merger between Solid- and Solution-Phase Synthesis

2000

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A polymer-assisted organic synthesis that combines the concept of solid-phase synthesis with the idea of polymer-supported scavenging reagents has recently appeared on the chemistry scene. This technique has frequently been termed the "resin-capture-release" methodology and is initiated by the immobilization of a small molecule on a polymeric support. This intermediate is subjected to a second transformation by adding a new reaction partner in solution. This reactant plays two roles: a) the chemical alteration of the polymer-bound intermediate and b) the simultaneous release of this reaction product from the resin back into solution. This new concept is presented and future prospects are discussed.

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Trifluoroacetylation of amines and amino acids by polymer-bound trifluoroacetylation reagents

Cited by 28 publications

References 3 publications

Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

Solid-supported reagents in organic synthesis

The “Resin-Capture-Release” Hybrid Technique: A Merger between Solid- and Solution-Phase Synthesis

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