Novel strategy for the synthesis of fluorinated β-amino acid derivatives from Δ2-oxazolines

Fustero, Santos; Salavert, Esther; Pina, Belén; Arellano, Carmen Ramírez de; Asensio, Amparo

doi:10.1016/s0040-4020(01)00539-7

Cited by 26 publications

(8 citation statements)

References 53 publications

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“…This indicates that the amino acid moieties in M1 and M2 could enhance the activity of thiourea derivatives against Acanthamoeba cells. Fustero et al [26] supported this finding by highlighting that in general, amino acid derivatives of compounds can exhibit a variety of biological properties. Meanwhile, Ye et al [27] emphasized that amino acids derivatives in compounds would give them a hydrophilic moiety which leads to high selectivity toward receptors.…”

Section: Resultsmentioning

confidence: 89%

Anti-Amoebic Properties of Carbonyl Thiourea Derivatives

2014

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Thiourea derivatives display a broad spectrum of applications in chemistry, various industries, medicines and various other fields. Recently, different thiourea derivatives have been synthesized and explored for their anti-microbial properties. In this study, four carbonyl thiourea derivatives were synthesized and characterized, and then further tested for their anti-amoebic properties on two potential pathogenic species of Acanthamoeba, namely A. castellanii (CCAP 1501/2A) and A. polyphaga (CCAP 1501/3A). The results indicate that these newly-synthesized thiourea derivatives are active against both Acanthamoeba species. The IC 50 values obtained were in the range of 2.39-8.77 µg·mL -1 (9.47-30.46 µM) for A. castellanii and 3.74-9.30 µg·mL -1 (14.84-31.91 µM) for A. polyphaga. Observations on the amoeba morphology indicated that the compounds caused the reduction of the amoeba size, shortening of their acanthopodia structures, and gave no distinct vacuolar and nuclear structures in the amoeba cells. Meanwhile, fluorescence microscopic observation using acridine orange and propidium iodide (AOPI) staining revealed that the synthesized compounds induced compromised-membrane in the amoeba cells. The results of this study proved that these new carbonyl thiourea derivatives, especially compounds M1 and M2 provide potent cytotoxic properties toward pathogenic Acanthamoeba to suggest that they can be developed as new anti-amoebic agents for the treatment of Acanthamoeba keratitis.

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Section: Resultsmentioning

confidence: 89%

Anti-Amoebic Properties of Carbonyl Thiourea Derivatives

2014

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“…Again, reduction of 73 with sodium borohydride and zinc iodide proceeded with acceptable diastereoselectivity, and the oxazoline 74 was finally transformed into the N-protected b-(trifluoromethyl)-bamino ester 75 by hydrolysis and esterification. 39…”

Section: Scheme 15mentioning

confidence: 99%

Synthesis of Fluorinated β-Amino Acids

Mikami¹,

Fustero²,

Sánchez‐Roselló³

et al. 2011

Synthesis

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The major goal of this review is to provide an overview of the general synthetic methods available in the literature for preparing fluorinated b-amino acids and their derivatives. These compounds have been employed in combination with non-fluorinated amino acids in the design of peptides and peptidomimetics for investigation of their proteolytic stability and influence of molecular composition on the folding properties and biological activity. Fluorinated b-amino acids serve as precursors for the b-lactam antibiotics and fluoroalkene dipeptide isosteres or as structural components of analogues of natural products. There are several general methods available for introducing into b-amino acids either one or two fluorine atoms at the a-position, as well as a-or b-fluoroalkyl substituents; these methods include reduction of fluorinated b-imino esters, biomimetic transamination of fluorinated carbonyl compounds, Michael-type addition to trifluorocrotonate and a-trifluoromethacrylate derivatives, and Reformatsky and Mannich-type reactions of fluorinated substrates. Fluorinated aziridines and b-lactams have been employed as synthetic intermediates for the preparation of the corresponding b-amino acids by facile ring-opening reactions. Other methods discussed in review are fluorination and trifluoromethylation of b-amino acid derivatives, reactions of organometallic reagents with fluorinated imines and related compounds, and metathesis reactions of fluorinated imino esters and imidoyl halides for the synthesis of cyclic derivatives.

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“…For instance, azaenolates derived from 2-alkyl-4,5-dihydrooxazoles and -thiazoles 9 afforded N-substituted C-protected b-enamino acid derivatives 10, which were isolated in good yields (60-92%) as a mixture of the imino and enamino tautomers (Scheme 3). 27 The condensation with ketimines 11 yielded fluorinated 1,3-diimines, which were isolated exclusively as the vinylogous amidine tautomers 12 in moderate to good yields (40-93%). Subsequent regioselective hydrolysis provided fluorinated b-enamino ketones 13 (Scheme 3).…”

Section: Scheme 2 Condensation Of Imidoyl Chlorides With Ester Enolatesmentioning

confidence: 99%

Nitrogen-Containing Organofluorine Derivatives: An Overview

Fustero¹,

Sanz‐Cervera²,

Aceña³

et al. 2009

Synlett

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Fluorinated organic compounds, in particular those containing nitrogen atoms, are popular targets in medicinal chemistry. They are obtained through chemical synthesis, usually by employing small, fluorinated molecules as starting building blocks. This account focuses on the reactivity and synthetic applications of different types of fluorinated building blocks. It summarizes recent methodologies developed in our and other laboratories for the synthesis of a variety of nitrogen-containing organofluorine compounds.

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Novel strategy for the synthesis of fluorinated β-amino acid derivatives from Δ2-oxazolines

Cited by 26 publications

References 53 publications

Anti-Amoebic Properties of Carbonyl Thiourea Derivatives

Anti-Amoebic Properties of Carbonyl Thiourea Derivatives

Synthesis of Fluorinated β-Amino Acids

Nitrogen-Containing Organofluorine Derivatives: An Overview

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