N-[(2,6-Dimethylphenoxy)alkyl]aminoalkanols—their physicochemical and anticonvulsant properties

Waszkielewicz, Anna M.; Cegła, Marek; Żesławska, Ewa; Nitek, Wojciech; Słoczyńska, Karolina; Marona, Henryk

doi:10.1016/j.bmc.2015.06.045

Cited by 19 publications

(49 citation statements)

References 23 publications

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“…As long as the linker between xanthonoxy and aminoalkanol moiety is concerned, among the used ethylene and propylene—propylene is more beneficial, on the basis of comparison between compounds 9 and 12 . This result is another surprise contrary to our findings in other aroxyalkylaminoalkanol derivatives, where ethylene is superior to propylene (structures I and II) …”

Section: Discussioncontrasting

confidence: 99%

“…The results of 9 and 12 suggest activity rather not of the compound itself, but of a metabolite. These results vary significantly from phenoxyalkylaminoalkanols, which exhibit activity immediately after administration and time of peak effect is usually 0.25 h or 0.5 h after administration . The results are presented in Table .…”

Section: Resultsmentioning

confidence: 89%

“…into mice. The preliminary evaluation was a qualitative assay which used small groups of animals and included three tests: maximal electroshock seizure (MES), subcutaneous pentylenetetrazol (ScMet), and neurotoxicity (rotarod), noted at 30 min and 4 h after administration…”

Section: Methodsmentioning

confidence: 99%

“…Aminoalkanol derivatives and their anticonvulsant activity have been subjected our research for many years, with variously substituted aroxyalkyl or aroxyacyl moiety. Such aroxy group formerly constituted 2,3‐dimethyl‐, 2,4‐dimethyl, 2,5‐dimethyl‐, 2,6‐dimethyl‐, as well as 2‐chloro‐5‐methyl‐, 4‐chloro‐2‐methyl, 4‐chloro‐3‐methyl, or 2‐chloro‐6‐methylphenol . Among the published results, the most active compounds were found ( R )‐2‐{[2‐(2,6‐dimethylphenoxy)ethyl]amino}propan‐1‐ol (I) (6) and ( S )‐2‐{[2‐(2,6‐dimethylphenoxy)ethyl]amino}butan‐1‐ol hydrochloride (II) (Figure ) …”

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confidence: 99%

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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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Section: Discussioncontrasting

confidence: 99%

Section: Resultsmentioning

confidence: 89%

Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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

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“…Epilepsy is caused by multiple factors such as genes, trauma, neurodegeneration and intoxication [2]. Previous investigations have proved that individuals with epilepsy have higher mortality rates than the general population [3][4].…”

Section: Introductionmentioning

confidence: 99%

Anticonvulsant and sedative effect of <i>Fufang Changniu</i> pills and probable mechanism of action in mice

Zhang¹,

Lu²,

Zhang³

et al. 2016

Trop. J. Pharm Res

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Synthesis of N‐(phenoxyalkyl)‐, N‐{2‐[2‐(phenoxy)ethoxy]ethyl}‐ or N‐(phenoxyacetyl)piperazine Derivatives and Their Activity Within the Central Nervous System

et al. 2019

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Depression, anxiety and epilepsy share some etiology factors, causing frequently observed multimodal activity of centrally active compounds. This might raise the risk of central adverse effects of potential drugs, but on the other hand ‐ in a light of common comorbidity of these diseases ‐ also make an opportunity for avoiding polypragmasy. The presented study combines rational drug design methods, chemical synthesis, receptor studies and in vivo pharmacological screening (mice, i. p.) in order to obtain new centrally active piperazine derivatives in a context of their potential multimodality, investigate the mechanism of their activity and establish relationship between their structure, molecular mechanism and in vivo central activity(‐ies). The most promising pharmacological profile showed 1‐(2‐(2,5‐dimethylphenoxy)ethyl)‐4‐phenylpiperazine dihydrochloride (1), which was active in the four‐plate test (anxiolytic‐like activity) at 1.25 mg/kg b.w. and possessed high affinities towards several tested molecular targets (5‐HT1A Ki=35 nM ‐ weak antagonist, 5‐HT2A Ki=121 nM, 5‐HT7 Ki=130 nM ‐ weak antagonist, α1 Ki=82 nM, μ Ki=240 nM).

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N-[(2,6-Dimethylphenoxy)alkyl]aminoalkanols—their physicochemical and anticonvulsant properties

Cited by 19 publications

References 23 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

Anticonvulsant and sedative effect of <i>Fufang Changniu</i> pills and probable mechanism of action in mice

Synthesis of N‐(phenoxyalkyl)‐, N‐{2‐[2‐(phenoxy)ethoxy]ethyl}‐ or N‐(phenoxyacetyl)piperazine Derivatives and Their Activity Within the Central Nervous System

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