1153594-86-5Relevant academic research and scientific papers
Synthesis and antimicrobial evaluation of promising 7-arylamino-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylates and their halogenated amino compounds for treating Gram-negative bacterial infections
Novais, Juliana S.,Campos, Vinicius R.,Silva, Ana Carolina J. A.,De Souza, Maria C. B. V.,Ferreira, Vitor F.,Keller, Vitor G. L.,Ferreira, Matheus O.,Dias, Flaviana R. F.,Vitorino, Maíra I.,Sathler, Plínio C.,Santana, Marcos V.,Resende, Jackson A. L. C.,Castro, Helena C.,Cunha, Anna C.
, p. 18311 - 18320 (2017/04/06)
Pathogenic bacteria may cause serious infections, such as pneumonia, which can be fatal especially to immunosuppressed individuals. Hospitalized patients are particularly susceptible to antibiotic-resistant infections, which are worsened when caused by resistant Gram-negative pathogens due to there being few therapeutic options available. Thus, this work describes the synthesis and in vitro antimicrobial profile of 7-arylamino-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylates and their halogenated aminoquinones against Gram-positive and Gram-negative bacteria. Interestingly, these bioactive substances have shown promising activity against Gram-negative pathogenic strains. Among these derivatives, two non-halogenated amino compounds exhibited promising MIC and MBC values (MIC = MBC = 1-2 μg mL?1) against Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853, two Gram-negative strains of clinical importance. In addition, mono- and di-brominated aminoquinones were also effective in preventing the growth of E. coli (MIC = MBC = 2-4 μg mL?1). The in vitro hemocompatibility evaluation showed a low toxicity profile for the active aminoquinones in hemolysis assays. These results suggest that these substances have potential for exploring the design of new antimicrobial prototypes against Gram-negative bacteria.
On-water reactivity and regioselectivity of quinones in C-N coupling with amines: Experimental and theoretical study
Martinez-Cifuentes, Maximiliano,Clavijo-Allancan, Graciela,Di Vaggio-Conejeros, Carolina,Weiss-Lopez, Boris,Araya-Maturana, Ramiro
, p. 217 - 224 (2014/03/21)
A study about the oxidative coupling of some representative carbo-and heterocyclic non-symmetrical quinones with aryl-and alkylamines, was carried out comparing dichloromethane and water as reaction mediums. We found that the on-water reactions gave better or, at worst, the same results as a conventional organic medium like dichloromethane. Descriptors derived from conceptual density functional theory and approaches of electrostatic nature, such as the molecular electrostatic potential, were used to explain the observed chemical reactivity and regioselectivity. Further, the on-water conditions were used to obtain 24 new aminoquinones with potential biological activity.
Studies on quinones. Part 45: Novel 7-aminoisoquinoline-5,8-quinone derivatives with antitumor properties on cancer cell lines
Valderrama, Jaime A.,Andrea Ibacache,Arancibia, Veronica,Rodriguez, Jaime,Theoduloz, Cristina
experimental part, p. 2894 - 2901 (2009/09/06)
A variety of 7-aminoisoquinoline-5,8-quinone derivatives were prepared from 2,5-dihydroxyacetophenone, methyl aminocrotonate, and the corresponding amines, through a highly efficient three-step sequence. The members of this series were tested on normal hu
