RESUMO
A new series of N-(substituted-phenyl)-2-[5-(quinoxalin-2-yloxymethyl)-[1,3,4] oxadiazol-2-ylsulfanyl]-acetamides (5a-o) was designed and synthesised from the parent compound 2-hydroxy quinoxaline (1) through a multistep reaction sequence and was characterised by spectral and elemental analyses. All of the compounds synthesised were evaluated for their antimicrobial and antiprotozoal activities. The results revealed that quinoxaline-based 1,3,4-oxadiazoles displayed promising antibacterial, antifungal and anti-Trypanosoma cruzi activities compared with reference drugs, particularly the lead compound 5l in a short-term in vivo model in T. cruzi.
Assuntos
Anti-Infecciosos/administração & dosagem , Anti-Infecciosos/farmacologia , Oxidiazóis/administração & dosagem , Oxidiazóis/farmacologia , Quinoxalinas/administração & dosagem , Quinoxalinas/farmacologia , Trypanosoma cruzi/efeitos dos fármacos , Animais , Bactérias/efeitos dos fármacos , Doença de Chagas/tratamento farmacológico , Modelos Animais de Doenças , Fungos/efeitos dos fármacos , Masculino , Camundongos , Estrutura Molecular , Oxidiazóis/síntese química , Oxidiazóis/química , Quinoxalinas/síntese química , Quinoxalinas/químicaRESUMO
An expedient and concise Ugi-based unified approach for the rapid assembly of quinoxaline frameworks has been developed. This convergent and versatile method uses readily available commercial reagents, does not require advanced intermediates, and exhibits excellent bond-forming efficiency, thus exemplifying the operationally simple synthesis of quinoxaline libraries.
Assuntos
Quinoxalinas/síntese química , Bibliotecas de Moléculas Pequenas/síntese química , Técnicas de Química Combinatória/economia , Técnicas de Química Combinatória/métodos , Quinoxalinas/química , Bibliotecas de Moléculas Pequenas/química , Fatores de TempoRESUMO
An efficient method for constructing quinoxalinone-N-oxides from cyanoacetanilides has been developed. This transformation can be achieved using inexpensive reagents and molecular oxygen under mild conditions, thus offering a practical pathway to quinoxalinone-containing pharmaceuticals such as ataquimast and opaviraline.
Assuntos
Acetanilidas/química , Óxidos/síntese química , Quinoxalinas/síntese química , Catálise , Química Orgânica/economia , Química Orgânica/métodos , Ciclização , Estrutura Molecular , Oxirredução , Óxidos/química , Quinoxalinas/químicaRESUMO
Real-time, noninvasive assessment of glomerular filtration rate (GFR) is essential not only for monitoring critically ill patients at the bedside, but also for staging and monitoring patients with chronic kidney disease. In our pursuit to develop exogenous luminescent probes for dynamic optical monitoring of GFR, we have prepared and evaluated Eu(3+) complexes of several diethylenetriamine pentaacetate (DTPA)-monoamide ligands bearing molecular "antennae" to enhance metal fluorescence via intramolecular ligand-metal fluorescence resonance energy transfer process. The results show that Eu-DTPA-monoamide complex 18b, which contains a quinoxanlinyl antenna, exhibits large (ca. 2700-fold) Eu(3+) fluorescence enhancement. Indeed, complex 18b exhibits the highest fluorescent enhancement observed thus far in the DTPA-type metal complexes. The renal clearance property was assessed using the corresponding radioactive (111)In complex 18a, and the data suggest that this complex clears via a complex mechanism that includes glomerular filtration.