Anticonvulsant evaluation of aminoalkanol derivatives of 2- and 4-methylxanthone

Szkaradek, Natalia; Gunia, Agnieszka; Waszkielewicz, Anna M.; Antkiewicz-Michaluk, Lucyna; Cegła, Marek; Szneler, Edward; Marona, Henryk

doi:10.1016/j.bmc.2012.12.051

Cited by 21 publications

(15 citation statements)

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“…We also have published derivatives of xanthone exhibiting anticonvulsant activity in maximal electroshock (MES) seizures in mice or rats, with aminoalkanol moieties such as R,S ‐6‐chloro‐2‐{[(1‐hydroxypropan‐2‐yl)amino]methyl}‐9 H‐ xanthen‐9‐one (III), ( S )‐6‐chloro‐2‐{[(1‐hydroxybutan‐2‐yl)amino]methyl}‐9 H‐ xanthen‐9‐one (IV), and without aminoalkanol moieties, such as 2‐[(4‐benzylpiperazin‐1‐yl)methyl]‐6‐methoxy‐9 H‐ xanthen‐9‐one (V) (Figure ) . So far, according to our experience, position of substituents in the xanthone rings plays crucial role and the most active compounds III–V contain substituents at positions C2 and C6 of the xanthone structure.…”

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

et al. 2016

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A series of new xanthone derivatives have been synthesized and evaluated for their anticonvulsant properties in the maximal electroshock, subcutaneous metrazole tests and for neurotoxicity in the rotarod in mice, i.p. and rats, p.o. Compound 9: R,S-2-{2-[(1-hydroxybutan-2-yl]amino)ethoxy}-9H-xanthen-9-one and compound 12: R,S-2-{3-[(1-hydroxybutan-2-yl)amino]propoxy}-9H-xanthen-9-one exerted activity in rats, p.o. 2 and 4 h after administration, respectively. Therefore, metabolic stability of the compounds was evaluated with use of rat microsomes, resulting in half-life t 136 and 108 min, respectively, indicating that either the metabolites are very active or the parent compounds exert ADME properties other than metabolism which influence the late onset of activity.

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

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“…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. In our previous work, we focused on searching for xanthones with antimicrobial activity.…”

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confidence: 89%

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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“…This work was supported financially by grants from the National Natural Science Foundation of PRC (21002015) Xanthone, also named as dibenzo-γ-pyrone, is a fundamental structural framework of active ingredients in many medicinal plants, which derivatives have broad pharmacological activities, such as antioxidant (Cheng et al, 2011), antitumor (Sousa et al, 2009), anticonvulsant (Szkaradek et al, 2013) and inhibition of neuraminidase activity (Dao et al, 2012). The title compound in this study is a new xanthone derivative, which was synthesized by bromination of 1,3dihydroxy-xanthen-9-one (Liu et al, 2006) with NBS.…”

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2,4-Dibromo-1,3-dihydroxy-9H-xanthen-9-one

Huang¹,

Yang²,

Huang³

et al. 2013

Acta Crystallogr E Struct Rep Online

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The title compound, C13H6Br2O4, derived from xanthone, a fundamental structural framework of active ingredients in many medicinal plants, and was synthesized by bromination of 1,3-dihydroxyxanthen-9-one with N-bromosuccinimide. The molecular conformation is essentially planar, the dihedral angle between the benzene rings being 1.1 (4)°. This conformation is favorable for the formation of an intramolecular O—H⋯O hydrogen bond between a hydroxy group and the xanthone carbonyl group. In the crystal, molecules are associated into chains along the b-axis direction via C=O⋯H—O hydrogen bonds involving the other hydroxy group.

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Anticonvulsant evaluation of aminoalkanol derivatives of 2- and 4-methylxanthone

Cited by 21 publications

References 17 publications

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

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

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

2,4-Dibromo-1,3-dihydroxy-9H-xanthen-9-one

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