Lithium butylchalcogenolate induced Michael-aldol tandem sequence: easy and rapid access to highly functionalized organochalcogenides and unsaturated compounds

Keppler, Artur F.; Gariani, Rogério A.; Lopes, Danilo G.; Comasseto, J. V.

doi:10.1016/j.tetlet.2009.02.158

Cited by 16 publications

(13 citation statements)

References 15 publications

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“…Encouraged by these findings, we (34,35,36,38, and 40 g/ml, respectively). The data represent the means Ϯ the standard errors from three independent experiments (*, P Ͻ 0.05).…”

Section: To 6)mentioning

confidence: 60%

“…The organotelluride compounds (Fig. 1) were synthesized as previously described (38)(39)(40)(41). All compounds were stored in a desiccator at 4°C, and stock solutions were prepared in DMSO.…”

Section: Methodsmentioning

confidence: 99%

“…Gray bars indicate the percent Nile red accumulation relative to the sensitive control strain AD/pABC3 in the presence of PBS (pH 7.2), which was set to 100% of Nile red-preloaded AD/CaMDR1 cells incubated in the presence of buffer only (PBS, pH 7.2), buffer including the vehicle control of 0.5% DMSO, or buffer plus 100 M concentrations of compounds 1 to 5 (34,35,37,38, and 40 g/ml, respectively), dissolved in DMSO, as indicated. The data represent the means Ϯ the standard errors from three independent experiments (*, P Ͻ 0.05 compared to AD/CaMDR1).…”

Section: Figmentioning

confidence: 99%

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Synthetic Organotellurium Compounds Sensitize Drug-Resistant Candida albicans Clinical Isolates to Fluconazole

Sá

Toledo

Gonçalves

et al. 2017

Antimicrob Agents Chemother

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Invasive Candida albicans infections are a serious health threat for immunocompromised individuals. Fluconazole is most commonly used to treat these infections, but resistance due to the overexpression of multidrug efflux pumps is of grave concern. This study evaluated the ability of five synthetic organotellurium compounds to reverse the fluconazole resistance of C. albicans clinical isolates. Compounds 1 to 4, at Ͻ10 g/ml, ameliorated the fluconazole resistance of Saccharomyces cerevisiae strains overexpressing the major C. albicans multidrug efflux pumps Cdr1p and Mdr1p, whereas compound 5 only sensitized Mdr1p-overexpressing strains to fluconazole. Compounds 1 to 4 also inhibited efflux of the fluorescent substrate rhodamine 6G and the ATPase activity of Cdr1p, whereas all five of compounds 1 to 5 inhibited Nile red efflux by Mdr1p. Interestingly, all five compounds demonstrated synergy with fluconazole against efflux pump-overexpressing fluconazoleresistant C. albicans clinical isolates, isolate 95-142 overexpressing CDR1 and CDR2, isolate 96-25 overexpressing MDR1 and ERG11, and isolate 12-99 overexpressing CDR1, CDR2, MDR1, and ERG11. Overall, organotellurium compounds 1 and 2 were the most promising fluconazole chemosensitizers of fluconazole-resistant C. albicans isolates. Our data suggest that these novel organotellurium compounds inhibit pump efflux by two very important and distinct families of fungal multidrug efflux pumps: the ATP-binding cassette transporter Cdr1p and the major facilitator superfamily transporter Mdr1p.

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“…Encouraged by these findings, we (34,35,36,38, and 40 g/ml, respectively). The data represent the means Ϯ the standard errors from three independent experiments (*, P Ͻ 0.05).…”

Section: To 6)mentioning

confidence: 60%

Section: Methodsmentioning

confidence: 99%

Section: Figmentioning

confidence: 99%

See 1 more Smart Citation

Synthetic Organotellurium Compounds Sensitize Drug-Resistant Candida albicans Clinical Isolates to Fluconazole

Sá

Toledo

Gonçalves

et al. 2017

Antimicrob Agents Chemother

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show abstract

“…48 Finally, the conjugate addition of the soft selenide nucleophile to methyl acrylate was pursued. 49,50 Unexpectedly, the product isolated from this reaction was the primary alcohol instead of the Michael adduct. Presumably, the conjugate addition of selenide occurred and the resulting product was reduced by the excess of sodium borohydride.…”

Section: Resultsmentioning

confidence: 92%

Synthesis of seleno-carbohydrates derived from d-galactose

Braga

Wouters

Zerillo

et al. 2010

Carbohydrate Research

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“…Furthermore, was proven that lithium organochalcogenides are good nucleophiles in Michael-aldol-tandem reactions and the resulting adducts are considered immediate precursors of Baylis-Hillman adducts 2 .…”

Section: Introductionmentioning

confidence: 99%