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1.
J Am Chem Soc ; 145(36): 19513-19517, 2023 09 13.
Artigo em Inglês | MEDLINE | ID: mdl-37642301

RESUMO

Azomethine imines are valuable substrates for chemical synthesis in organic solvents that often require anhydrous conditions. Here, we introduce C,N-cyclic-N'-acyl azomethine imines (AMIs) to bioorthogonal reactions in an aqueous environment. These AMIs are stable under physiological conditions and react rapidly (k2 = 0.1-250 M-1 s-1, depending on pH) and chemoselectively with isonitriles in the presence of biological nucleophiles, including thiols. Live-cell imaging of cell-surface-bound isonitriles underlines the biocompatibility of the AMI-isonitrile ligation, and simultaneous one-pot triple-protein labeling demonstrates its orthogonality to commonly used bioorthogonal reactions, such as the SPAAC and iEDDA ligations.


Assuntos
Compostos Azo , Iminas , Membrana Celular , Biologia
2.
J Org Chem ; 88(2): 1155-1167, 2023 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-36580673

RESUMO

4-Aryl-5-allyl-N-fluoroalkyl-1,2,3-triazoles available by a three-component reaction of fluoroalkyl azides, copper acetylides, and allyl halides underwent aluminum halide-mediated transformation to N-(4-halo-2-aryl-cyclopentenyl) imidoyl halides by cyclization of vinyl cation intermediates, followed by halide capture. Utilization of the cyclic products was demonstrated by the synthesis of N-alkenyl amides, amidines, isoquinolines, and tetrazoles or by the subsequent modification of the cyclopentene ring.

3.
Beilstein J Org Chem ; 17: 2657-2662, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34795803

RESUMO

The stereoselective Suzuki-Miyaura cross-coupling of (Z)-ß-enamido triflates is demonstrated. Depending on the nature of the ligand in the palladium catalyst, either retention or inversion of the configuration during the synthesis of ß,ß-diaryl-substituted enamides is observed. Thus, the method provides synthetic access to both isomers of the target enamides from (Z)-ß-enamido triflates.

4.
Org Lett ; 23(11): 4224-4227, 2021 06 04.
Artigo em Inglês | MEDLINE | ID: mdl-34032455

RESUMO

A reaction of N-sulfonyl-1,2,3-triazole with boron trifluoride etherate afforded a (Z)-ß-ensulfonylamido fluoride instead of the previously erroneously assigned E isomer. The correction of the stereochemistry was based on a ge-1D ROESY NMR experiment and X-ray crystal structure analyses. Application of the reaction to N-fluoroalkyl-1,2,3-triazoles afforded new (Z)-ß-enamido fluorides in a stereoselective manner. A mechanism involving coordination of BF3 with the triazole ring and vinyl diazonium and vinyl cation intermediates was proposed.

6.
Chemistry ; 25(32): 7640-7644, 2019 Jun 07.
Artigo em Inglês | MEDLINE | ID: mdl-30977565

RESUMO

N-Fluoroalkylated 1,2,3-triazoles in the presence of triflic acid or fluorosulfonic acid underwent a cascade reaction consisting of triazole protonation, ring opening, nitrogen elimination, sulfonate addition, HF elimination, and hydrolysis to furnish novel trifluoromethanesulfonyloxy- or fluorosulfonyloxy-substituted enamides, respectively, in a highly stereoselective fashion. The vinyl triflates underwent cross-coupling reactions to a variety of substituted enamides and serve as sources of the aminovinyl cations. In reactions with triflic acid, electron-rich triazoles afforded 2-fluoroalkylated oxazoles.

7.
Chem Commun (Camb) ; 54(26): 3258-3261, 2018 Mar 27.
Artigo em Inglês | MEDLINE | ID: mdl-29537032

RESUMO

A rhodium-catalyzed transannulation via ring-opening of N-(per)fluoroalkyl-substituted 1,2,3-triazoles followed by cycloaddition with different nitriles, enol ethers, isocyanates and silyl ketene acetals under microwave heating provided a highly efficient route to previously unreported N-(per)fluoroalkyl-substituted imidazoles, pyrroles, imidazolones and pyrrolones, respectively. These reactions were found to be applicable to the synthesis of a variety of 5-membered heterocycles bearing different (per)fluoroalkyl substituents as well as both electron-donating and electron-withdrawing groups attached to the heterocyclic core.

8.
J Med Chem ; 61(7): 3027-3036, 2018 04 12.
Artigo em Inglês | MEDLINE | ID: mdl-29498519

RESUMO

Here, we have identified the interaction site of the contraceptive drug gamendazole using computational modeling. The drug was previously described as a ligand for eukaryotic translation elongation factor 1-α 1 (eEF1A1) and found to be a potential target site for derivatives of 2-phenyl-3-hydroxy-4(1 H)-quinolinones (3-HQs), which exhibit anticancer activity. The interaction of this class of derivatives of 3-HQs with eEF1A1 inside cancer cells was confirmed via pull-down assay. We designed and synthesized a new family of 3-HQs and subsequently applied isothermal titration calorimetry to show that these compounds strongly bind to eEF1A1. Further, we found that some of these derivatives possess significant in vitro anticancer activity.


Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Indazóis/metabolismo , Fator 1 de Elongação de Peptídeos/efeitos dos fármacos , Quinolonas/síntese química , Quinolonas/farmacologia , Sítios de Ligação/efeitos dos fármacos , Linhagem Celular Tumoral , Biologia Computacional , Humanos , Ligantes , Modelos Moleculares , Conformação Molecular , Fator 1 de Elongação de Peptídeos/biossíntese , Relação Estrutura-Atividade
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