Antileishmanial effect of new indeno-1,5-naphthyridines, selective inhibitors of Leishmania infantum type IB DNA topoisomerase

Tejería, Ana; Pérez-Pertejo, Yolanda; Reguera, Rosa M.; Balaña‐Fouce, Rafael; Alonso, C.; Fuertes, Marı́a; González, M.; Rubiales, Gloria; Palacios, Francisco

doi:10.1016/j.ejmech.2016.09.017

Cited by 45 publications

(17 citation statements)

References 65 publications

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“…The first report for the synthesis of substituted 7 H -indeno[2,1- c ][1,5]naphthyridine derivatives was carried out by Palacios and colleagues [ 24 , 25 , 26 ].…”

Section: Synthesis Of Fused 15-naphthyridinesmentioning

confidence: 99%

“…The transformation of 1,2,3,4-tetrahydroindeno[1,5]naphthyridine 50 into dehydrogenated derivatives 51 was performed by our group [ 24 , 25 ] by dehydrogenation under microwave irradiation (150 W), with one equivalent of DDQ ( Scheme 45 ) with total conversion of starting material. Alternatively, dehydrogenation of tetrahydroindeno[1,5]naphthyridine 50 with a ethyl carboxylate group (R = CO 2 Et) was performed by using Mn(AcO) 3 as oxidant in acetic acid at room temperature and the corresponding 7 H -indeno[2,1- c ][1,5]naphthyridine 51 (R = CO 2 Et) was obtained.…”

Section: Reactivity Of Fused 15-naphthyridinesmentioning

confidence: 99%

“…It is worth noting that indeno[1,5]naphthyridine 51d ( Figure 9 ) showed a very high inhibition of TopI activity and the highest cytotoxic effect, with an IC 50 of 1.7 ± 0.1 µM, against the A549 cell line in vitro. The interesting biochemical and biological features found for these derivatives provide a promising basis for further development of biologically active fused naphthyridines [ 25 ].…”

Section: Biological Activity Of Fused 15-naphthyridinesmentioning

confidence: 99%

“…The inhibition of leishmania (LTopIB) and human TopIB (HTopIB) of tetrahydroindeno[1,5]naphthyridines 50 and indeno[1,5]naphthyridines 51 ( Scheme 15 , vide supra) were studied and their antileishmanial activity on promastigotes and amastigote-infected splenocytes of Leishmania infantum were evaluated [ 25 ]. Some of the prepared heterocycles showed selective inhibition of LtopIB, while no inhibition of hTopIB was observed at evaluated conditions.…”

Section: Biological Activity Of Fused 15-naphthyridinesmentioning

confidence: 99%

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Fused 1,5-Naphthyridines: Synthetic Tools and Applications

et al. 2020

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Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in the fields of synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. In this review, a wide range of synthetic protocols for the construction of this scaffold are presented. For example, Friedländer, Skraup, Semmlere-Wolff, and hetero-Diels-Alder, among others, are well known classical synthetic protocols used for the construction of the main 1,5-naphthyridine scaffold. These syntheses are classified according to the nature of the cycle fused to the 1,5-naphthyridine ring: carbocycles, nitrogen heterocycles, oxygen heterocycles, and sulphur heterocycles. In addition, taking into account the aforementioned versatility of these heterocycles, their reactivity is presented as well as their use as a ligand for metal complexes formation. Finally, those fused 1,5-naphthyridines that present biological activity and optical applications, among others, are indicated.

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“…The first report for the synthesis of substituted 7 H -indeno[2,1- c ][1,5]naphthyridine derivatives was carried out by Palacios and colleagues [ 24 , 25 , 26 ].…”

Section: Synthesis Of Fused 15-naphthyridinesmentioning

confidence: 99%

Section: Reactivity Of Fused 15-naphthyridinesmentioning

confidence: 99%

Section: Biological Activity Of Fused 15-naphthyridinesmentioning

confidence: 99%

Section: Biological Activity Of Fused 15-naphthyridinesmentioning

confidence: 99%

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Fused 1,5-Naphthyridines: Synthetic Tools and Applications

et al. 2020

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“…Thus, novel compounds and/or strategies are needed, including delivery systems [52] and new molecules, such as AMPs [53]. Membranes and DNA topoisomerases have attracted considerable interest as potential targets for novel antiparasitic therapeutics [54],[55].…”

Section: Measuring the Efficacy Of Antimicrobials Against Protozoamentioning

confidence: 99%

New and old tools to evaluate new antimicrobial peptides

et al. 2018

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The emergence of antimicrobial resistance due to the overuse of antimicrobials together with the existence of naturally untreatable infections well demonstrates the need for new instruments to fight microbes. Antimicrobial peptides (AMPs) are a promising family of molecules in this regard, because they abundantly occur in nature and the results of preliminary studies of their clinical potential have been encouraging. However, further progress will benefit from the standardization of research methods to assess the antimicrobial properties of AMPs. Here we review the diverse methods used to study the antimicrobial power of AMPs and recommend a pathway to explore new molecules. The use of new methodologies to quantitatively evaluate the physical effect on bacterial biofilms such as force spectroscopy and surface cell damage evaluation, constitute novel approaches to study new AMPs.

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Regioselective Synthesis of Benzo[h][1,6]‐naphthyridines and Chromenopyrazinones through Alkyne Cyclization

2017

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A regioselective approach to the synthesis of benzo[h][1,6]‐naphthyridine and chromenopyrazinone derivatives was developed. The synthetic route to benzo[h][1,6]‐naphthyridines involves the N‐propargylation of aromatic aminobenzaldehydes, followed by reaction with propargylamine in the presence of DBU (1,8‐diazabicyclo[5.4.0]undec‐7‐ene). For the synthesis of chromenopyrazine and chromenopyrazinone derivatives, the acetonitrile group was introduced to salicylaldehyde derivatives, and a DBU‐promoted cyclization reaction between aldehydes and propargylamine gave the chromenopyrazines. The intramolecular heterocycloaddition reaction between the triple bond and the azadiene, which is formed as an intermediate, gave the desired structures.

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Antileishmanial effect of new indeno-1,5-naphthyridines, selective inhibitors of Leishmania infantum type IB DNA topoisomerase

Cited by 45 publications

References 65 publications

Fused 1,5-Naphthyridines: Synthetic Tools and Applications

Fused 1,5-Naphthyridines: Synthetic Tools and Applications

New and old tools to evaluate new antimicrobial peptides

Regioselective Synthesis of Benzo[h][1,6]‐naphthyridines and Chromenopyrazinones through Alkyne Cyclization

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