Synthesis, in silico, in vitro and in vivo evaluations of isatin aroylhydrazones as highly potent anticonvulsant agents
[Display omitted] •(Z)-Isatin aroylhydrazones (5a-e and 6a-e) were synthesized as anticonvulsant agents.•Most of compounds were effective against MES-induced seizures.•Compounds 6a and 6e showed 100% protection at the dose of 5 mg/kg.•Pharmacokinetics properties of 6a and 6e were evaluated computati...
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| Published in | Bioorganic chemistry Vol. 112; p. 104943 |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
Elsevier Inc
01.07.2021
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| Subjects | |
| Online Access | Get full text |
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| Abstract | [Display omitted]
•(Z)-Isatin aroylhydrazones (5a-e and 6a-e) were synthesized as anticonvulsant agents.•Most of compounds were effective against MES-induced seizures.•Compounds 6a and 6e showed 100% protection at the dose of 5 mg/kg.•Pharmacokinetics properties of 6a and 6e were evaluated computationally and experimentally.•6a and 6e had no significant cytotoxicity against neuronal and hepatic cells at conventional doses.
In this study, a series of new isatin aroylhydrazones (5a-e and 6a-e) was synthesized and evaluated for their anticonvulsant activities. The (Z)-configuration of compounds was confirmed by 1H NMR. In vivo studies using maximal electroshock (MES) and pentylenetetrazole (PTZ) models of epilepsy in mice revealed that while most of compounds had no effect on chemically-induced seizures at the higher dose of 100 mg/kg but showed significant protection against electrically-induced seizures at the lower dose of 5 mg/kg. Certainly, N-methyl analogs 6a and 6e were found to be the most effective compounds, displaying 100% protection at the dose of 5 mg/kg. Protein binding and lipophilicity(logP) of the selected compounds (6a and 6e) were also determined experimentally. In silico evaluations of title compounds showed acceptable ADME parameters, and drug-likeness properties. Distance mapping and docking of the selected compounds with different targets proposed the possible action of them on VGSCs and GABAA receptors. The cytotoxicity evaluation of 6a and 6e against SH-SY5Y and Hep-G2 cell lines indicated safety profile of compounds on the neuronal and hepatic cells. |
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| AbstractList | [Display omitted]
•(Z)-Isatin aroylhydrazones (5a-e and 6a-e) were synthesized as anticonvulsant agents.•Most of compounds were effective against MES-induced seizures.•Compounds 6a and 6e showed 100% protection at the dose of 5 mg/kg.•Pharmacokinetics properties of 6a and 6e were evaluated computationally and experimentally.•6a and 6e had no significant cytotoxicity against neuronal and hepatic cells at conventional doses.
In this study, a series of new isatin aroylhydrazones (5a-e and 6a-e) was synthesized and evaluated for their anticonvulsant activities. The (Z)-configuration of compounds was confirmed by 1H NMR. In vivo studies using maximal electroshock (MES) and pentylenetetrazole (PTZ) models of epilepsy in mice revealed that while most of compounds had no effect on chemically-induced seizures at the higher dose of 100 mg/kg but showed significant protection against electrically-induced seizures at the lower dose of 5 mg/kg. Certainly, N-methyl analogs 6a and 6e were found to be the most effective compounds, displaying 100% protection at the dose of 5 mg/kg. Protein binding and lipophilicity(logP) of the selected compounds (6a and 6e) were also determined experimentally. In silico evaluations of title compounds showed acceptable ADME parameters, and drug-likeness properties. Distance mapping and docking of the selected compounds with different targets proposed the possible action of them on VGSCs and GABAA receptors. The cytotoxicity evaluation of 6a and 6e against SH-SY5Y and Hep-G2 cell lines indicated safety profile of compounds on the neuronal and hepatic cells. In this study, a series of new isatin aroylhydrazones (5a-e and 6a-e) was synthesized and evaluated for their anticonvulsant activities. The (Z)-configuration of compounds was confirmed by H NMR. In vivo studies using maximal electroshock (MES) and pentylenetetrazole (PTZ) models of epilepsy in mice revealed that while most of compounds had no effect on chemically-induced seizures at the higher dose of 100 mg/kg but showed significant protection against electrically-induced seizures at the lower dose of 5 mg/kg. Certainly, N-methyl analogs 6a and 6e were found to be the most effective compounds, displaying 100% protection at the dose of 5 mg/kg. Protein binding and lipophilicity(logP) of the selected compounds (6a and 6e) were also determined experimentally. In silico evaluations of title compounds showed acceptable ADME parameters, and drug-likeness properties. Distance mapping and docking of the selected compounds with different targets proposed the possible action of them on VGSCs and GABA receptors. The cytotoxicity evaluation of 6a and 6e against SH-SY5Y and Hep-G2 cell lines indicated safety profile of compounds on the neuronal and hepatic cells. |
| ArticleNumber | 104943 |
| Author | Valipour, Mehdi Honarchian Masihi, Patrick Ahangar, Nematollah Sadati-Ashrafi, Fatemehsadat Kazemi Komishani, Fatemeh Ghasemian, Majid Irannejad, Hamid Shakiba, Aidin Tajbakhsh, Mahmood Emami, Saeed Rasoulian, Maria |
| Author_xml | – sequence: 1 givenname: Saeed surname: Emami fullname: Emami, Saeed email: semami@mazums.ac.ir organization: Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran – sequence: 2 givenname: Mehdi surname: Valipour fullname: Valipour, Mehdi organization: Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran – sequence: 3 givenname: Fatemeh surname: Kazemi Komishani fullname: Kazemi Komishani, Fatemeh organization: Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran – sequence: 4 givenname: Fatemehsadat surname: Sadati-Ashrafi fullname: Sadati-Ashrafi, Fatemehsadat organization: Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran – sequence: 5 givenname: Maria surname: Rasoulian fullname: Rasoulian, Maria organization: Student Research Committee, Ramsar Campus, Mazandaran University of Medical Sciences, Ramsar, Iran – sequence: 6 givenname: Majid surname: Ghasemian fullname: Ghasemian, Majid organization: Department of Clinical Biochemistry, School of Medicine, Shahid Beheshti University of Medical Sciences (SBMU), Tehran, Iran – sequence: 7 givenname: Mahmood surname: Tajbakhsh fullname: Tajbakhsh, Mahmood organization: Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar, Iran – sequence: 8 givenname: Patrick surname: Honarchian Masihi fullname: Honarchian Masihi, Patrick organization: Student Research Committee, Ramsar Campus, Mazandaran University of Medical Sciences, Ramsar, Iran – sequence: 9 givenname: Aidin surname: Shakiba fullname: Shakiba, Aidin organization: Student Research Committee, Ramsar Campus, Mazandaran University of Medical Sciences, Ramsar, Iran – sequence: 10 givenname: Hamid surname: Irannejad fullname: Irannejad, Hamid organization: Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran – sequence: 11 givenname: Nematollah surname: Ahangar fullname: Ahangar, Nematollah email: n.ahangar@gums.ac.ir organization: Department of Pharmacology, School of Medicine, Guilan University of Medical Sciences, Rasht, Iran |
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| Keywords | MES Anticonvulsant agents Epilepsy PTZ Hydrazide-hydrazones |
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•(Z)-Isatin aroylhydrazones (5a-e and 6a-e) were synthesized as anticonvulsant agents.•Most of compounds were effective against MES-induced... In this study, a series of new isatin aroylhydrazones (5a-e and 6a-e) was synthesized and evaluated for their anticonvulsant activities. The (Z)-configuration... |
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| SubjectTerms | Anticonvulsant agents Epilepsy Hydrazide-hydrazones MES PTZ |
| Title | Synthesis, in silico, in vitro and in vivo evaluations of isatin aroylhydrazones as highly potent anticonvulsant agents |
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