Design and development of trifluoromethylated enaminone derivatives as potential anticonvulsants

Amaye, Isis J.; Harper, Tawes; Jackson-Ayotunde, Patrice L.

doi:10.1016/j.jfluchem.2021.109886

Cited by 9 publications

(1 citation statement)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Enaminones are recognized for their high reactivity related to their special structure containing the conjugated system N-C=C-C=O that combines both the nucleophilicity of the enamine group with two electron-rich sites and the electrophilicity of the 1 3 α,β-unsaturated ketone with two electron-deficient sites. That is what made them very useful as intermediates in the synthesis of acyclic, cyclic, and heterocyclic systems [2][3][4][5][6]. Besides their use as precursors, β-enaminone-containing molecules have also been employed for medical purposes and remained very useful, showing several activities such as antibacterial [7], antitubercular [8], anti-inflammatory [9], anticonvulsant [10], antitumoral [11], antinociceptive [12], and antidepressant activities [13].…”

Section: Introductionmentioning

confidence: 99%

New efficient synthesis, spectroscopic characterization, and X-ray analysis of novel β-enaminocarboxamide derivatives

et al. 2023

View full text Add to dashboard Cite

A new series of β-enaminocarboxamide was synthesized via the addition of chlorosulfonyl isocyanate to β-enaminones. The prepared intermediates were converted to corresponding β-enaminocarboxamides by removal of the chlorosulfonyl group using methanol. The resulting compounds were obtained in excellent yields in the range of (80-92%) and were characterized by 1 H, 13 C, HMBC, HSQC NMR spectroscopy, and IR spectroscopy as well as elemental analysis. 1 H-NMR spectrum showed a non-equivalence of the primary amide protons which was due to H-bonding. β-enaminocarboxamide 5h was obtained as a crystal and was subjected to X-ray analysis. Results showed that 5h crystallizes in the monoclinic crystal system with C2/c space group and the ORTEP confirmed the presence of intramolecular H-bonds.

show abstract

Section: Introductionmentioning

confidence: 99%

New efficient synthesis, spectroscopic characterization, and X-ray analysis of novel β-enaminocarboxamide derivatives

et al. 2023

View full text Add to dashboard Cite

show abstract

Design and synthesis of novel cycloalkanecarboxamide parabanic acid hybrids as anticonvulsants

Abd-Allah,

Abd El-Maksoud,

Elbaset

et al. 2023

Med Chem Res

View full text Add to dashboard Cite

Aiming to develop novel anticonvulsant agents a new series of novel cycloalkanecarboxamide parabanic acid hybrids series 8, 9 and 10 possessing the essential structure requirements for anticonvulsant activity was synthesized starting from cycloalkanones. All final target compounds were primary screened for chemically and electrically induced seizures using pentylenetetrazole “scPTZ” and maximal electroshock seizure “MES” models. In phase I anticonvulsant evaluation compounds 8b and 10b exhibited the highest potency among all the target compounds with 100% protection towards chemically induced seizures. Results of phase II anticonvulsant screening showed that compounds 8b and 10b are more potent than standard drug ethosuximide by about 11 and 9 fold, respectively. Regarding MES test, compounds 8b and 9a-d exhibited 100% protection with ED50 values ranged between 0.107–0.177 mmol/Kg. All final compounds did not display any signs of motor impairment in the neurotoxicity screening test. Also, compounds 8a, 9a-d and 10b were devoid of hepatotoxicity as shown by measurement of serum levels of liver enzymes, albumin as well as total protein. Moreover, the cyclohexyl derivative 10b produced a significant increase of Gamma-aminobutyric acid “GABA” brain’s content of mice compared to control group confirmed its GABAergic modulating activity. Molecular docking, physicochemical and pharmacokinetic properties were carried out for all compounds as well. These outcomes support that cycloalkanecarboxamide parabanic acid hybrid is a promising scaffold to pave the way towards further development of novel class of antiepileptic drugs.

show abstract

2D polymeric lanthanide(III) compounds based on novel bright green emitting enaminone ligand

Smirnova

Ivanova

Pozdnyakov

et al. 2022

Inorganica Chimica Acta

View full text Add to dashboard Cite

Design and development of trifluoromethylated enaminone derivatives as potential anticonvulsants

Cited by 9 publications

References 36 publications

New efficient synthesis, spectroscopic characterization, and X-ray analysis of novel β-enaminocarboxamide derivatives

New efficient synthesis, spectroscopic characterization, and X-ray analysis of novel β-enaminocarboxamide derivatives

Design and synthesis of novel cycloalkanecarboxamide parabanic acid hybrids as anticonvulsants

2D polymeric lanthanide(III) compounds based on novel bright green emitting enaminone ligand

Contact Info

Product

Resources

About