Preliminary Evaluation of Anticonvulsant Activity of Some Aminoalkanol and Amino Acid Cinnamic Acid Derivatives

Gunia, Agnieszka; Waszkielewicz, Anna M.; Cegła, Marek; Marona, Henryk

doi:10.2174/157018012798192982

Cited by 17 publications

(12 citation statements)

References 23 publications

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“…administration in maximal electroshock and 6-Hz test, respectively. 12,13 In the present article we report enantiomeric N-trans-cinnamoyl derivatives of 2-aminopropan-1-ols and 2-aminobutan-1-ols. We used crystallographic methods to evaluate the configuration of 2-aminopropan-1-ols derivatives.…”

mentioning

confidence: 86%

“…Compounds 1-4 were obtained by means of a previously published procedure of N-acylation. 12,13 In the reactions, enantiomeric aminoalkanols were used: R-2-aminopropan-1-ol for 1, S-2-aminopropan-1-ol for 2, R-2aminobutan-1-ol for 3, and S-2-aminobutan-1-ol for 4. Appropriate aminoalkanol was dissolved in 5.5% solution of K 2 CO 3 .…”

Section: Synthesis Of Compounds 1-4mentioning

confidence: 99%

“…), N‐trans ‐cinnamoyl derivative of R , S ‐2‐aminopropan‐1‐ol, showed ED 50 s of 86.6 and 60.9 mg/kg when tested in mice after intraperitoneal (i.p.) administration in maximal electroshock and 6‐Hz test, respectively …”

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confidence: 99%

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Anticonvulsant Activity of Enantiomeric N‐trans‐Cinnamoyl Derivatives of 2‐Aminopropan‐1‐ols and 2‐Aminobutan‐1‐ols

et al. 2016

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Epilepsy, one of the most frequent neurological disorders, is still insufficiently treated in about 30% of patients. As a consequence, identification of novel anticonvulsant agents is an important issue in medicinal chemistry. In the present article we report synthesis, physicochemical, and pharmacological evaluation of N-trans-cinnamoyl derivatives of R and S-2-aminopropan-1-ol, as well as R and S-2-aminobutan-1-ol. The structures were confirmed by spectroscopy and for derivatives of 2-aminopropan-1-ols the configuration was evaluated by means of crystallography. The investigated compounds were tested in rodent models of seizures: maximal electroshock (MES) and subcutaneous pentetrazol test (scPTZ), and also in a rodent model of epileptogenesis: pilocarpine-induced status prevention. Additionally, derivatives of 2-aminopropan-1-ols were tested in benzodiazepine-resistant electrographic status epilepticus rat model as well as in vitro for inhibition of isoenzymes of cytochrome P450. All of the tested compounds showed promising anticonvulsant activity in MES. For R(-)-(2E)-N-(1-hydroxypropan-2-yl)-3-phenylprop-2-enamide pharmacological parameters were found as follows: ED50 = 76.7 (68.2-81.3) mg/kg (MES, mice i.p., time = 0.5 h), ED50 = 127.2 (102.1-157.9) mg/kg (scPTZ, mice i.p., time = 0.25 h), TD50 = 208.3 (151.4-230.6) mg/kg (rotarod, mice i.p., time = 0.25 h). Evaluation in pilocarpine status prevention proved that all of the reported compounds reduced spontaneous seizure activity and act as antiepileptogenic agents. Both enantiomers of 2-aminopropan-1-ols did not influence cytochrome P450 isoenzymes activity in vitro and are likely not to interact with CYP substrates in vivo. Chirality 28:482-488, 2016. © 2016 Wiley Periodicals, Inc.

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confidence: 86%

Section: Synthesis Of Compounds 1-4mentioning

confidence: 99%

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Anticonvulsant Activity of Enantiomeric N‐trans‐Cinnamoyl Derivatives of 2‐Aminopropan‐1‐ols and 2‐Aminobutan‐1‐ols

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“…The preliminary evaluation of anticonvulsant activity and neurotoxicity of a series of aminoalkanol (21)(22)(23)(24) and amino acid (25-28) derivatives of trans-cinnamic acid as well as aminoalkanol derivatives of α-phenylcinnamic acid (29)(30). Compound 22 was formerly identified in Oxytropis pseudoglandulosa [62] and its anticancer in vitro activity was reported [63]. The flunarizine can protect rats and mice in controlling the seizure induced by MES test [64].…”

Section: No Cinnamic Acid Derivatives Pharmacological Activity Mechamentioning

confidence: 99%

Synthetic methods and pharmacological potential of some cinnamic acid analogues particularly against convulsions

Asif

Imran

2019

Prog. Chem. Biochem. Res.

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“…Antiepileptic drugs (AED) should be prescribed and used carefully as these drugs can cause severe side effects eventually affecting quality of life. Their use is associated with significant dose-related toxicity and adverse effects such as tremor, blurred vision, neurotoxicity and sometimes death due to either hepatic damage or from aplastic anaemia (Ghogare et al, 2010;Gunia et al, 2010;Hu et al, 2010).…”

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confidence: 99%

Studies on new substituted pyridazinones: synthesis and biological evaluation

Asif

Singh

Khan

et al. 2018

Braz. J. Pharm. Sci.

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We report herein the synthesis and pharmacological evaluation of a new series of 6-aryl-2-(imidazol-1-yl/1,2,4-triazol-1-yl)-2-methyl-4,5-dihydro-(2H)-pyridazin-3-one (3a-j) as potential anticonvulsant and antitubercular agents. The title compounds were prepared by reacting 6-aryl-4,5-dihydro-(2H)pyridazin-3-one (2a-e) with formaldehyde and secondary cyclic amine imidazole or 1,2,4-triazole as per Mannich reaction. Anticonvulsant activity of pyridazinone derivatives was tested at 50 mg.kg-1 dose level against maximal electroshock (MES), isoniazid (INH, 250 mg.kg-1) and pentylenetetrazole (PTZ at 80 mg.kg-1) induced seizure methods. Phenytoin sodium (25 mg.kg-1) and sodium valproate (100 mg. kg-1) were used as reference drugs for comparison purpose. In-vitro antitubercular activity was tested by Microplate Alamar Blue assay (MABA) method and the results were compared with clinically used antitubercular agents such as INH, Pyrazinamide (PZA) and Streptomycin (STM). None of the screened compounds were found to be neurotoxic at a dose level of 100 mg.kg-1. All the screened compounds (3a-j) significantly reduced the MES, INH and PTZ induced convulsions and thus showed good anticonvulsant activity. The minimum inhibitory concentration (MIC) of the title compounds against M. tuberculosis ranged from 1.6 µg/mL to 6.25 µg/mL in comparison to INH, PZA (3.125 µg/mL) and STM (6.25 µg/ mL) which indicated good antitubercular activity.

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Preliminary Evaluation of Anticonvulsant Activity of Some Aminoalkanol and Amino Acid Cinnamic Acid Derivatives

Cited by 17 publications

References 23 publications

Anticonvulsant Activity of Enantiomeric N‐trans‐Cinnamoyl Derivatives of 2‐Aminopropan‐1‐ols and 2‐Aminobutan‐1‐ols

Anticonvulsant Activity of Enantiomeric N‐trans‐Cinnamoyl Derivatives of 2‐Aminopropan‐1‐ols and 2‐Aminobutan‐1‐ols

Synthetic methods and pharmacological potential of some cinnamic acid analogues particularly against convulsions

Studies on new substituted pyridazinones: synthesis and biological evaluation

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