Synthesis and antiprotozoal activity of furanchalcone–quinoline, furanchalcone–chromone and furanchalcone–imidazole hybrids

García, Elisa; Coa, Juan Carlos; Otero, Elver; Cardá, Miguel; Vélez, Iván Darío; Robledo, Sara M.; Cardona, Wilson

doi:10.1007/s00044-017-2076-6

Cited by 38 publications

(27 citation statements)

References 35 publications

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“…This could be due to the presence of the α,β‐unsaturated moiety of the chalcone that easily reacts with thiol and amino groups. [ 7 ] Also, 2‐pyrazolines (nitrogen‐containing heterocyclic compound) could form hydrogen bonding [ 60 ] in the active site of the enzymes of Leishmania .…”

Section: Resultsmentioning

confidence: 99%

“…[ 4 ] Neglected tropical diseases are an important cause of mortality in tropical and subtropical regions from 149 countries, [ 5,6 ] affecting more than one billion people [ 6 ] with malaria, leishmaniasis, and Chagas disease, among others, which require toxic and expensive chemotherapy agents, such as pentavalent antimonials, miltefosine, amphotericin B, benznidazole, and nifurtimox. [ 5,7 ] Unfortunately, these treatments are contraindicated and in some cases are not effective in the chronic phase due to parasite resistance. [ 7 ] However, these emerging resistances could be overcome by the synthesis and modification of new biologically active molecules.…”

Section: Introductionmentioning

confidence: 99%

“…[ 5,7 ] Unfortunately, these treatments are contraindicated and in some cases are not effective in the chronic phase due to parasite resistance. [ 7 ] However, these emerging resistances could be overcome by the synthesis and modification of new biologically active molecules. Several researchers have demonstrated a broad spectrum of biological activities of the 2‐aminothiazole (2‐AT) derivatives as antibacterial, [ 8 ] antifungal, [ 9 ] antitumoral, [ 10 ] antimalarial, [ 11–13 ] antidiabetic, [ 14 ] anti‐inflammatory, [ 15 ] and antiviral [ 16 ] agents (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Cuartas

Robledo

Vélez

et al. 2020

Archiv der Pharmazie

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A new series of N-substituted pyrazoline derivatives 6a-g, 7a-g, 8a-g, and 9a-g was synthetized by reaction of hydrazine derivatives and chalcone-thiazole hybrids bearing nitrogen mustard 5a-g. The chalcones 5a-g were obtained by Claisen-Schmidt condensation of thiazole-2-nitrogen mustard 3 and selected acetophenones 4a-g. These new compounds 6/7/8/9a-g were screened for their antifungal activity against Cryptococcus neoformans, with IC 50 values of 3.9-7.8 µg/ml for the N-3, 5-dichlorophenyl pyrazolines 9e-g. Interestingly, those compounds show low cytotoxic effects toward erythrocytes (RBC). In addition, N-acetyl (6a,b) and N-formyl pyrazolines (7a, 7b, 7c, and 7g) showed inhibitory activity against methicillinsusceptible Staphylococcus aureus, methicillin-resistant S. aureus, and vancomycinintermediate S. aureus, with the most important minimum inhibitory concentration values ranging from 31.25 to 125 µg/ml. Regarding the antiprotozoal activity, thiazolyl-pyrazolines 9g, 8f, and 7c display high activity against Plasmodium falciparum, Leishmania (V) panamensis, and Trypanosoma cruzi, with EC 50 values of 11.80, 6.46, and 4.98 μM, respectively, and with 7c being approximately 2.6-fold more potent than benznidazole with a selectivity index of 1.61 on U-937 human cells, showing promising potential as a novel antitrypanosomal agent. K E Y W O R D S antibacterial activity, antifungal activity, antiprotozoal activity, chalcone, pyrazoline

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Cuartas

Robledo

Vélez

et al. 2020

Archiv der Pharmazie

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“…The methylation of the hydroxyl group ( 4 c ) leads to the loss of activity. These results agree with other reports for several chalcones, coumarins, cinnamic esters and triclosan‐caffeic acid hybrids . The effect of the hydroxyl groups may be due to a better molecular recognition ability towards target bioreceptors upon hydrogen bond formation .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, In Silico Studies, Antiprotozoal and Cytotoxic Activities of Quinoline‐Biphenyl Hybrids

et al. 2020

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The synthesis, in silico studies, antiprotozoal and cytotoxic activities of eleven quinoline‐biphenyl hybrids are described herein. The structure of the synthesized products was elucidated by a combination of spectrometric analyses. The synthesized compounds were evaluated against Plasmodium falciparum, and amastigotes forms both Leishmania (V) panamensis and Trypanosoma cruzi. Cytotoxicity was evaluated against human U‐937 macrophages. 8‐phenylquinoline (4 a) showed similar activity than meglumine antimoniate and 4‐(quinolin‐8‐yl)phenol (4 b) exhibited an activity similar to that of benznidazole. 8‐(3,4‐dimethoxyphenyl) quinoline (4 k) showed the best activity against P. falciparum. Although these compounds were toxic for mammalian U‐937 cells, however they may still have potential to be considered as candidates for drug development because of their antiparasite activity. Molecular docking was used to determine the in silico inhibition of some of the designed compounds against PfLDH and cruzipain, two important pharmacological targets involved in antiparasitic diseases. All hybrids were docked to the three‐dimensional structures of PfLDH and T. cruzi cruzipain as enzymes using AutoDock Vina. Notably, the docking results showed that the most active compounds 4‐(quinolin‐8‐yl)phenol (4 b, CE50: 11.33 μg/mL for T. cruzi) and 8‐(3,4‐dimethoxyphenyl) quinoline (4 k, CE50: 8.84 μg/mL for P. falciparum) exhibited the highest scoring pose (−7.5 and −7.7 kcal/mol, respectively). This result shows a good correlation between the predicted scores with the experimental data profile, suggesting that these ligands could act as competitive inhibitors of PfLDH or T. cruzi cruzipain enzymes, respectively. Finally, in silico ADME studies of the quinoline hybrids showed that these novel compounds have suitable drug‐like properties, making them potentially promising agents for antiprotozoal therapy.

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“…Nitrogen-heterocycles play a predominant role in medicinal chemistry due to their pharmacological activities. The quinoline derivatives play various biological activates such as anticancer [1], anti-HIV [2], antimicrobial [3], antituberculosis [4], antiviral [5], antimalarial [6], antioxidant [7], anti-inflammatory [8], antiprotozoal [9] and some of the quinoline derivatives found in marked drugs including as chloroquine, piperaquine, pyronaridine, ciprofloxacin, lenvatinib and tipifamib. In addition, morpholine core moiety is also important in pharmacological industry due to its antimicrobial [10] and anti-inflammatory [11] activities.…”

Section: Introductionmentioning

confidence: 99%

Green Synthetic Protocol for (E)-1-Aryl-3-(2-morpholinoquinolin- 3-yl)prop-2-en-1-ones and Their Antimicrobial Activity

Subrahmanyam

Anna

2019

Asian J. Chem.

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We report here an easy, efficient and green synthetic protocol for the (E)-1-aryl-3-(2-morpholinoquinolin-3-yl)prop-2-en-1-ones by the Claisen-Schmidt condensation of 2-morpholinoquinoline-3-carbaldehyde and different substituted acetophenones by using 1-butyl-3-methylimidazolium tetrafluoroborate (Bmim)BF4. The compounds were characterized by using 1H NMR, 13C NMR and mass spectral data and screened there in vitro antimicrobial activity against different bacterial and fungal organisms.

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Synthesis and antiprotozoal activity of furanchalcone–quinoline, furanchalcone–chromone and furanchalcone–imidazole hybrids

Cited by 38 publications

References 35 publications

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Synthesis, In Silico Studies, Antiprotozoal and Cytotoxic Activities of Quinoline‐Biphenyl Hybrids

Green Synthetic Protocol for (E)-1-Aryl-3-(2-morpholinoquinolin- 3-yl)prop-2-en-1-ones and Their Antimicrobial Activity

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