Design, synthesis, and anticonvulsant activity of some derivatives of xanthone with aminoalkanol moieties

Waszkielewicz, Anna M.; Słoczyńska, Karolina; Pękala, Elżbieta; Żmudzki, Paweł; Siwek, Agata; Gryboś, Anna; Marona, Henryk

doi:10.1111/cbdd.12842

Cited by 25 publications

(27 citation statements)

References 33 publications

(44 reference statements)

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“…Waszkielewicz et al [156] proposed also a series of novel xanthone derivatives. All compounds were obtained using 2-hydroxyxanthone as the starting reagent, which was subjected to aminolysis in toluene in the presence of K 2 CO 3 , or in DMF with a catalytic amount of KI.…”

Section: Synthetic Routesmentioning

confidence: 99%

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Klein‐Júnior

Campos

Niero

et al. 2020

Chemistry & Biodiversity

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Xanthones are a class of heterocyclic natural products that have been widely studied for their pharmacological potential. In fact, they have been serving as scaffolds for the design of derivatives focusing on drug development. One of the main study targets of xanthones is their anticancer activity. Several compounds belonging to this class have already demonstrated cytotoxic and antitumor effects, making it a promising group for further exploration. This review therefore focuses on recently published studies, emphasizing their natural and synthetic sources and describing the main mechanisms of action responsible for the anticancer effect of promising xanthones.

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Section: Synthetic Routesmentioning

confidence: 99%

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Klein‐Júnior

Campos

Niero

et al. 2020

Chemistry & Biodiversity

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“…The synthesis and physicochemical properties of the compounds 1-3, 8-11, 13 and 14 have already been reported (references are given in Table 1). 13 [21] with thionyl chloride in toluene according to a published procedure. [22] After termination of the reaction, the solvent and unreacted thionyl chloride were distilled in vacuo and the dry residue was recrystallized from the mixture of acetone:EtOH .…”

Section: Chemistrymentioning

confidence: 99%

“…Of the new compounds with possible antifungal activity, chlorine derivatives of 9 H ‐xanthen‐9‐one and phenoxyethyl amines attracted our special attention. Xanthones are known for their multifocal biological properties including antibacterial and antifungal activities. The antimycobacterial, anti‐ Helicobacter and antifungal activities of some of these compounds have been already confirmed.…”

Section: Introductionmentioning

confidence: 99%

Preliminary antifungal activity assay of selected chlorine‐containing derivatives of xanthone and phenoxyethyl amines

et al. 2018

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The aim of this study was to evaluate antifungal activity in a diverse group of chlorine-containing xanthone and phenoxyethyl amine derivatives - and to select the most promising compounds for further studies. The antifungal efficacy of 16 compounds was tested with qualitative and quantitative methods against both reference and clinical strains of dermatophytes, moulds and yeasts. The disc-diffusion method has demonstrated that from 16 tested compounds, 7 possess good antifungal activity against dermatophytes and/or moulds while none of them has shown good efficacy against yeasts or bacterial strains. The most active compounds (2, 4, 10, 11, 12, 15, 16) were tested quantitatively by broth dilution method to obtain MIC values. The MIC values against dermatophytes ranged from 8 to 64 μg/ml. Compound 2 was the most active one against dermatophytes (MIC and MIC were 8 μg/ml). The MIC values for moulds ranged from 16 to 256 μg/ml. Compound 4 was the most active one against moulds, with MIC and MIC values amounting to 32 μg/ml. Among the tested compounds, compound 4 (derivative of xanthone) was the most active one and expressed good antifungal efficacy against clinical strains of dermatophytes and moulds. However, another xanthone derivative (compound 2) was the most active and selective against dermatophytes.

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“…Epilepsy is a common and chronic brain disorder characterized by unpredictable recurrent seizures (Abd‐Allah, Aboutabl, Aboul‐Enein, & El‐Azzouny, ). Despite the presence of many antiepileptic drugs (AEDs), approximately 30% of patients still suffer from uncontrolled episodes (Abd‐Allah et al, ; Abram et al, ; Siddiqui et al, ; Waszkielewicz et al, ). Moreover, AEDs have numerous undesirable side effects including neurotoxicity, which is very common and dose‐dependent (Edayadulla & Ramesh, ; Sangh Partap, Akhtar, Yar, Hassan, & Siddiqui, ; Rybka et al, ; St Louis, ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in vivo and in silico evaluation of novel 2,3‐dihydroquinazolin‐4(1H)‐one derivatives as potential anticonvulsant agents

Kothayer

Ibrahim

Soltan

et al. 2018

Drug Development Research

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In light of the pharmacophoric structural requirements for achieving anticonvulsant activity, a series of N‐(1‐methyl‐4‐oxo‐2‐un/substituted‐1,2‐dihydroquinazolin‐3[4H]‐yl)benzamide (4a‐g) and N‐(1‐methyl‐4‐oxo‐2‐un/substituted‐1,2‐dihydroquinazolin‐3[4H]‐yl)‐2‐phenylacetamide (4h‐n) derivatives were synthesized in two steps starting from the reaction of N‐methyl isatoic anhydride with the appropriate hydrazide and followed by condensation with the appropriate aldehyde. The anticonvulsant activities of the synthesized compounds were evaluated according to the anticonvulsant drug development (ADD) programme protocol. Among the synthesized compounds, 4n showed promising activity in both the maximal electroshock (MES) and pentylenetetrazole (PTZ) tests with median effective dose (ED50) values of 40.7 and 6 mg/kg, respectively. The six most promising derivatives, 4b, 4a, 4c, 4f, 4j, and 4i, showed very low ED50 values in the PTZ test (3.1, 4.96, 8.68, 9.89, 12, and 13.53 mg/kg, respectively). All the tested compounds showed no to low neurotoxicity in the rotarod test with a wide therapeutic index. Docking studies of compound 4n suggested that GABAA binding could be the mechanism of action of these derivatives. The in silico drug likeliness parameters indicated that none of the designed compounds violate Lipinski's rule of five and that they are able to cross the blood–brain barrier. Hit, Lead & Candidate Discovery

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Design, synthesis, and anticonvulsant activity of some derivatives of xanthone with aminoalkanol moieties

Cited by 25 publications

References 33 publications

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Preliminary antifungal activity assay of selected chlorine‐containing derivatives of xanthone and phenoxyethyl amines

Synthesis, in vivo and in silico evaluation of novel 2,3‐dihydroquinazolin‐4(1H)‐one derivatives as potential anticonvulsant agents

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