Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series

Roussaki, Marina; Hall, Belinda S.; Lima, Sofia A. Costa; Cordeiro-da-Silva, Anabela; Wilkinson, Shane R.; Detsi, Anastasia

doi:10.1016/j.bmcl.2013.09.047

Cited by 48 publications

(14 citation statements)

References 33 publications

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“…As discussed before, chalcones represent an important class of compounds with trypanocidal activity. [33][34][35][36][37] Based on this previously determined biological activity, we prepared and evaluated the nor-b-lapachone-based chalcone hybrids 17-21.…”

Section: Biological and Electrochemical Analysismentioning

confidence: 99%

“…32 Chalcones can be readily synthesized by the Claisen-Schmidt condensation method, 33 and they represent a key moiety in medicinal chemistry, displaying a wide range of pharmacological activities. 34 Hybrids of chalcone with quinolinone, 35 paullone 36 and benzoxaborole 37 have shown signicant activity against pathogenic trypanosomatids and low cytotoxicity to mammalian cells (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

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On the investigation of hybrid quinones: synthesis, electrochemical studies and evaluation of trypanocidal activity

et al. 2015

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Section: Biological and Electrochemical Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

On the investigation of hybrid quinones: synthesis, electrochemical studies and evaluation of trypanocidal activity

et al. 2015

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“…Nevertheless, in situ generated hydrochloric acid (HCl) catalysis was unsuccessful when applied to the synthesis of diphenolic chalcone 18. Thus, it has been prepared under microwave (MW) irradiations in the presence of piperidine [23]. In this work two other synthetic chalcones 12 and 14, bearing a phenol function on the C-2 ' position, have been prepared through selective demethylation of the corresponding 2'-methoxychalcones 13 and 15 in the presence of aluminum chloride (AlCl 3 ) [24].…”

Section: Chemistry and Clogpmentioning

confidence: 99%

Novel Insights into the Mode of Action of Vasorelaxant Synthetic Polyoxygenated Chalcones

Legeay

Tran

Abatuci

et al. 2020

IJMS

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Polyphenols consumption has been associated with a lower risk of cardiovascular diseases (CVDs) notably through nitric oxide (NO)- and estrogen receptor α (ERα)-dependent pathways. Among polyphenolic compounds, chalcones have been suggested to prevent endothelial dysfunction and hypertension. However, the involvement of both the NO and the ERα pathways for the beneficial vascular effects of chalcones has never been demonstrated. In this study, we aimed to identify chalcones with high vasorelaxation potential and to characterize the signaling pathways in relation to ERα signaling and NO involvement. The evaluation of vasorelaxation potential was performed by myography on wild-type (WT) and ERα knock-out (ERα-KO) mice aorta in the presence or in absence of the eNOS inhibitor Nω-nitro-L-arginine methyl ester (L-NAME). Among the set of chalcones that were synthesized, four (3, 8, 13 and 15) exhibited a strong vasorelaxant effect (more than 80% vasorelaxation) while five compounds (6, 10, 11, 16, 17) have shown a 60% relief of the pre-contraction and four compounds (12, 14, 18, 20) led to a lower vasorelaxation. We were able to demonstrate that the vasorelaxant effect of two highly active chalcones was either ERα-dependent and NO-independent or ERα-independent and NO-dependent. Thus some structure-activity relationships (SAR) were discussed for an optimized vasorelaxant effect.

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“…Bichalcophenes were chosen as many studies and patents of synthetic and naturally occurring chalcone derivatives have reported their potential against Leishmania [53, [55][56][57][58][59][60]. In the first work by Tidwell et al…”

Section: Pentamidinementioning

confidence: 99%

New perspectives for leishmaniasis chemotherapy over current anti-leishmanial drugs: a patent landscape

Machado-Silva

Guimarães

Tavares

et al. 2014

Expert Opinion on Therapeutic Patents

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Most patents related to drugs for leishmaniasis have not been produced by the pharmaceutical industry but rather by public research institutes or by universities, and the majority of the inventions disclosed are still in preclinical phase. There is an urgent need to find new ways of funding research for leishmaniasis drugs, incentivizing product development partnerships and pushing forward innovation.

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Synthesis and anti-parasitic activity of a novel quinolinone–chalcone series

Cited by 48 publications

References 33 publications

On the investigation of hybrid quinones: synthesis, electrochemical studies and evaluation of trypanocidal activity

On the investigation of hybrid quinones: synthesis, electrochemical studies and evaluation of trypanocidal activity

Novel Insights into the Mode of Action of Vasorelaxant Synthetic Polyoxygenated Chalcones

New perspectives for leishmaniasis chemotherapy over current anti-leishmanial drugs: a patent landscape

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