103344-70-3Relevant articles and documents
Divergent synthesis of (quinoxalin-2-yl)-1,3-oxazines and pyrimido[1,6-a]quinoxalines via the cycloaddition reaction of acyl(quinoxalinyl)ketenes
Kasatkina, Svetlana,Stepanova, Ekaterina,Dmitriev, Maksim,Mokrushin, Ivan,Maslivets, Andrey
supporting information, (2019/09/06)
A facile synthetic approach towards two distinct quinoxaline-based heterocyclic scaffolds has been developed from the cycloaddition of acyl(quinoxalinyl)ketenes with carbodiimides. The described reaction represents the first example of a divergent synthesis based on acyl(quinoxalinyl)ketenes providing (quinoxalin-2-yl)-1,3-oxazines or pyrimido[1,6-a]quinoxalines depending on the type of the acyl substituent in the ketenes. The key reactants, acyl(quinoxalinyl)ketenes, are generated in situ via the thermal decarbonylation of readily available pyrroloquinoxaline oxo-derivatives. The proposed diversity-oriented synthesis provides facile access to a library of skeletally diverse pharmaceutically interesting quinoxaline-based heterocycles from inexpensive reagents.
Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains
Cvijeti?, Ilija N.,Verbi?, Tatjana ?.,Ernesto de Resende, Pedro,Stapleton, Paul,Gibbons, Simon,Jurani?, Ivan O.,Drakuli?, Branko J.,Zloh, Mire
, p. 1474 - 1488 (2017/11/17)
Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents.
Synthesis of the ligand (z)-2-(3-methoxyphenylamino)-4-oxo-4-phenylbut-2- enoic acid and its antifungal activity against the wood stain fungi mucor plumbeus
Paz,Cajas-Madriaga,Torres,Moreno,Fernandez,Becerra,Silva
, p. 1713 - 1716 (2013/09/24)
The ligand (z)-2-(3-methoxyphenylamino)-4-oxo-4-phenylbut-2-enoic acid and its Ni (II) complex were synthesized and their antifungal activity against the fungi wood stain Mucor plumbeus was evaluated. The ligand displayed fungostatic activity while the Ni
