scholarly journals Application of Green Chemistry Principle in Synthesis of Phenytoin and Its Biogical Evaluation as Anticonvulsant Agents

2011 ◽  
Vol 8 (s1) ◽  
pp. S47-S52 ◽  
Author(s):  
Abhijit Kadam ◽  
Sampada Jangam ◽  
Rajesh Oswal
Keyword(s):  
Green Chemistry ◽  
Anticonvulsant Activity ◽  
Extra Cost ◽  
Green Solvent ◽  
Anticonvulsant Agents ◽  
H Nmr ◽  
Nmr Data ◽  
Anticonvulsant Agent ◽  
Seizure Models ◽  
Cns Stimulant

Phenytoin (5,5'-dipenylimidazolidine-2,4-dione) is the prime example of anticonvulsant agent. According to reported procedure, it is synthesized by condensation of benzil and urea in presence of base (30% w/v NaOH) using ethanol as solvent which itself acts as CNS stimulant. Removal of solvent after synthesis is most difficult and non-assured process. In case of phenytoin transformation in polymorphism plays an important role when solvent other than water is used. About 30% extra cost is calculated if solvent other than water is used. Therefore by application of green chemistry principle phenytoin was synthesized by condensation of benzil and urea in presence of base (30% NaOH) and water as green solvent. This compound was characterized on the basis of its spectral (IR,1H NMR) data and evaluated for anticonvulsant activity using MES induced and PTZ induced seizure models in Swiss albino mice. Significant anticonvulsant activity was found by using 25 mg/kg and 50 mg/kg of phenytoin compared with standard phenytoin at 25 mg/kg dose.

scholarly journals SYNTHESIS AND ANTICONVULSANT ACTIVITY (CHEMO SHOCK) OF N-1(SUBSTITUTED-N-4[(4-OXO-3-PHENYL-3, 4-DIHYDRO-QUINAZOLINE-2-YLMETHYL) SEMICARBAZONES

2017 ◽  
Vol 10 (4) ◽  
pp. 359 ◽  
Author(s):  
Meena K Yadav ◽  
Laxmi Tripathi ◽  
Diptendu Goswami
Keyword(s):  
Glutamate Receptor ◽  
Elemental Analysis ◽  
Anticonvulsant Activity ◽  
Chemical Structure ◽  
Shock Model ◽  
Analysis Techniques ◽  
H Nmr ◽  
Electronic Environment ◽  
Seizure Models ◽  
Anticonvulsant Activities

Objective: This work is designed at finding new structure leads with potential anticonvulsant activities of 4(3H)-quinazolinone pharmacophore scaffold.Methods: A new series of 4(3H)-quinazolinone pharmacophore was designed with substituted moieties possesses different electronic environment in the hope of developing potent and safe new effective compounds. In such fashion, in this paper, we report the synthesis and anticonvulsant activity (Chemo shock) of N-1(substituted-N-4[(4-oxo-3-phenyl-3, 4-dihydro-quinazoline-2-ylmethyl) semicarbazones 3A-d (1-7), 3B-d (1-7), 3C-d (1-7), their chemical structure were characterized using IR,  H-H NMR, and elemental analysis techniques. Their anticonvulsant activity was evaluated using chemicals strychnine, thiosemicarbazide and 4-aminopyridine induced seizure models at a dose of 30, 100, 300 mg/kg unto 2 hrs tests in mice. The rotarod assay was performed in mice to evaluate the neurotoxicity of the compounds. 1Results: Compounds 3C (d-4), 3B (d-4), and 3A (d-4) were observed to be most feasible to act against glutamate receptor for anticonvulsant activity.Conclusions: The results obtained revealed that numbers of novel quinazolinone semicarbazone derivatives are effective in chemical to induce (chemo shock) model and showing good anticonvulsant activity.Keywords: Quinazolinone, Semicarbazones, Strychnine, Thiosemicarbazide, 4-aminopyridine, Anticonvulsant activity, Chemo shock.

Design, Synthesis, Anticonvulsant Activity, Preclinical Study and Pharmacokinetic Performance of N-{[3-(4-chlorophenyl)-4-oxo-3, 4-dihydroquinazolin- 2-yl] methyl}, 2-[(2-isopropyl-5-methyl) 1-cyclo Hexylidene] Hydrazinecarboxamide

2019 ◽  
Vol 19 (1) ◽  
pp. 31-45
Author(s):  
Meena K. Yadav ◽  
Laxmi Tripathi
Keyword(s):  
Anticonvulsant Activity ◽  
Computational Study ◽  
Plasma Concentrations ◽  
Elimination Rate ◽  
Area Under The Curve ◽  
Preclinical Study ◽  
In Vivo Studies ◽  
Maximum Plasma ◽  
Seizure Models

Background: N-{[3-(4-chlorophenyl)-4-oxo-3, 4-dihydroquinazolin-2-yl] methyl}, 2-[(2- isopropyl-5-methyl) 1-cyclohexylidene] hydrazinecarboxamide QS11 was designed by computational study. It possessed essential pharmacophoric features for anticonvulsant activity and showed good docking with iGluRs (Kainate) glutamate receptor. Methods: QSAR and ADMET screening results suggested that QS11 would possess good potency for anticonvulsant activity. QS11 was synthesised and evaluated for its anticonvulsant activity and neurotoxicity. QS11 showed protection in strychnine, thiosemicarbazide, 4-aminopyridine and scPTZ induced seizure models and MES seizure model. QS11 showed higher ED50, TD50 and PI values as compared to the standard drugs in both MES and scPTZ screen. A high safety profile (HD50/ED50 values) was noted and hypnosis, analgesia, and anaesthesia were only observed at higher doses. No considerable increase or decrease in the concentration of liver enzymes was observed. Optimized QS11 was subjected to preclinical (in-vivo) studies and the pharmacokinetic performance of the sample was investigated. The result revealed that the pharmacokinetic performance of QS11 achieved maximum plasma concentrations (Cmax) of 0.315 ± 0.011 µg/mL at Tmax of 2.0 ± 0.13 h, area under the curve (AUC0-∞) value 4.591 ± 0.163 µg/ml x h, elimination half-life (T1/2) 6.28 ± 0.71 h and elimination rate constant was found 0.110 ± 0.013 h-1. Results and Conclusion: Above evidences indicate that QS11 could serve as a lead for development of new antiepileptic drugs.

Inhibited rotation of amide group around C N bond of nicotinamide in different solvents by 1 H NMR data

2017 ◽  
Vol 231 ◽  
pp. 238-241 ◽  
Author(s):  
G.A. Gamov ◽  
V.V. Aleksandriiskii ◽  
V.A. Sharnin
Keyword(s):  
Amide Group ◽  
H Nmr ◽  
Nmr Data

scholarly journals Synthesis and Pharmacological Evaluation of 2-(4-Halosubstituted phenyl)-4,5-diphenyl-1H-imidazoles

2008 ◽  
Vol 5 (3) ◽  
pp. 447-452 ◽  
Author(s):  
G. Nagalakshmi
Keyword(s):  
Anticonvulsant Activity ◽  
Glacial Acetic Acid ◽  
Ammonium Acetate ◽  
Antiinflammatory Activity ◽  
Aromatic Aldehydes ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
H Nmr ◽  
Structural Assignment ◽  
Paw Oedema

In the present study, 2-(4-halosubstituted phenyl)-4,5-diphenyl-1Himidazoles have been synthesized by refluxing benzil and ammonium acetate with different 4-halosubstituted aromatic aldehydes in glacial acetic acid. The structural assignment of this compound has been made on the basis of elemental analysis, UV, IR,1H NMR and Mass spectral data. Toxicity of the compound has been determined. The synthesized compound was evaluated for antiinflammatory activity against carrageenan induced paw oedema and anticonvulsant activity against maximal electro-shock-induced convulsions in rats.

SYNTHESIS OF NOVEL QUINAZOLIN-4(3H)-ONYL AZETIDINONES AS POTENTIAL ANTICONVULSANT AGENTS

INDIAN DRUGS ◽  
2017 ◽  
Vol 54 (11) ◽  
pp. 22-27
Author(s):  
A. Singh ◽  
Keyword(s):  
Magnetic Resonance ◽  
Acute Toxicity ◽  
Anticonvulsant Activity ◽  
Proton Magnetic Resonance ◽  
Acetyl Chloride ◽  
Mass Analysis ◽  
Substituted Anilines ◽  
Anticonvulsant Agents

A series of 4-(substituted aryl)- 1- [2’- methyl-6’- substituted anilino quinazolinon-4’-(3’H)-onyl ] -3- chloroazetidin- 2-ones 14-25 have been synthesized by addition of substituted anilines to 4-(substituted aryl)- 1- [2’- methyl-6’- bromoquinazolinon-4’-(3’H)-onyl ] -3- chloro- azetidin-2-ones 8-13 which in turn were prepared by the cycloaddition of triethylamine in dioxane to 3-(N-substituted benzylidene amino phenyl amido )-2-methyl-6-bromoquinazolin-4(3H)-ones 2-7 in presence of acetyl chloride. These compounds were screened for anticonvulsant activity and acute toxicity. Compound 4-(substituted aryl)- 1- [2’- methyl-6’- substituted anilino quinazolinon-4’-(3’H) – onyl ] -3- chloro-azetidinone showed most potent activity. The structure of all the synthesized compounds were delineated by elemental (C, H, N ) and spectra (IR, proton magnetic resonance and mass ) analysis.

scholarly journals Synthesis, Anticonvulsant Evaluation and Molecular Docking Studies of Novel Benzo[1,3]dioxol-5-yloxy-N′-(4-substituted benzylidene)acetohydrazide Derivatives

2019 ◽  
Vol 32 (1) ◽  
pp. 199-204
Author(s):  
Shailesh Kumar Singh ◽  
Laxmi Tripathi
Keyword(s):  
Molecular Docking ◽  
Mechanism Of Action ◽  
Anticonvulsant Activity ◽  
Docking Studies ◽  
Probable Mechanism ◽  
Aminobutyric Acid ◽  
Docking Score ◽  
Acid Receptor ◽  
Seizure Models ◽  
Gabaergic Activity

Novel (benzo[1,3]dioxol-5-yloxy)-N′-(4-substituted benzylidene)acetohydrazide derivatives were synthesized and their anticonvulsant activity evaluated by MES and scMET seizure models. Compound 2-(benzo[d][1,3]dioxol-5-yloxy)-N′-benzylideneacetohydrazide (4a) was found to be most potent in MES seizure test and showed no neurotoxicity at the highest administered dose. All the compounds showed high docking score with γ-aminobutyric acid receptor, GABAAR-β3 homopentamer (PDB ID: 4COF). Thus, the probable mechanism of action of benzo[1,3]dioxol-5-yloxy-N′-(4-substituted benzylidene)acetohydrazide derivatives (4a-h) may be augmentation of GABAergic activity.

scholarly journals STUDY OF CONFORMATIONAL PREFERENCES OF ERYTHRO-CAROLIGNAN E ASSESSED BY THE COUPLING BETWEEN H7'-H8' IN DIFFERENT NMR SOLVENTS

2016 ◽  
Vol 11 (1) ◽  
pp. 1
Author(s):  
Rudiyansyah Rudiyansyah ◽  
Ajuk Sapar ◽  
Masriani Masriani
Keyword(s):  
Ethanol Extract ◽  
Coupling Constant ◽  
Relative Configuration ◽  
H Nmr ◽  
Nmr Data ◽  
Conformational Preferences ◽  
Wood Bark

<p><em>Erythro</em>-carolignan E (<strong>1</strong>) has been obtained from the ethanol extract of the wood bark of <em>Durio affinis</em> Becc. This research was conducted in order to prove that conformational preferences of compound <strong>1</strong> were solvent dependent. On the basis of <sup>1</sup>H-NMR data, the relative configuration of compound <strong>1</strong> was characterized by a coupling constant (<sup>3</sup><em>J</em><sub>HH</sub>) value of 3.3 Hz at H-7' in CDCl<sub>3</sub>. The coupling constant (<sup>3</sup><em>J</em><sub>HH</sub>) values of H-7' in compound <strong>1</strong> has changed to 4.1 Hz and 5.3 Hz in pyridine-<em>d</em><sub>5</sub> and acetonitrile-<em>d</em><sub>3</sub> respectively. As a result, the conformation of compound <strong>1</strong> at C7'-C8' has changed in different NMR solvents.  In conclusion, structure of<em>erythro</em>-carolignan E that contains a dihydroxy group at C7'-C8' is able to change in different NMR solvent.</p>

scholarly journals Synthesis of Some Novel Fused Imidazo [2, 1-b] [1, 3] Thiazole and Imidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole Derivatives

2012 ◽  
Vol 9 (3) ◽  
pp. 1518-1525 ◽  
Author(s):  
Hamid Reza Jaberi ◽  
Hadi Noorizadeh
Keyword(s):  
Acetic Acid ◽  
Sodium Acetate ◽  
Carbon Disulphide ◽  
Thiazole Derivatives ◽  
H Nmr ◽  
Nmr Data ◽  
Elemental Analyses ◽  
New Compounds ◽  
Isoxazole Derivatives ◽  
C Nmr

In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR,1H NMR and13C NMR data.

Ein [1,3,4]Thiazaphospholidin, Darstellung und NMR-Daten / A [1,3,4]Thiazaphospholidine, Preparation and NMR Data

1987 ◽  
Vol 42 (1) ◽  
pp. 115-117 ◽  
Author(s):  
Gernot Heckmann ◽  
Ekkehard Fluck ◽  
Peter Kuhm
Keyword(s):  
Nmr Spectra ◽  
Resonance Mode ◽  
Triple Resonance ◽  
H Nmr ◽  
Nmr Data

Abstract Preparation and properties of a [1,3,4]thiazaphospholidine are described. The 31P. 13C and 1H NMR spectra in double and triple resonance mode are recorded and discussed in detail.

Preparation and characterization of some ruthenium(II) porphyrins containing tertiary phosphine axial ligands, including the crystal structure of (octaethylporphinato)bis(triphenylphosphine)ruthenium(II)

1984 ◽  
Vol 62 (4) ◽  
pp. 755-762 ◽  
Author(s):  
Sara Ariel ◽  
David Dolphin ◽  
George Domazetis ◽  
Brian R. James ◽  
Tak W. Leung ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Phosphine Ligands ◽  
Tertiary Phosphine ◽  
X Ray ◽  
Porphyrin Complex ◽  
H Nmr ◽  
Axial Ligands ◽  
Nmr Data ◽  
Phosphine Complex

The ruthenium(II) porphyrin complex Ru(OEP)(PPh3)2 (OEP = the dianion of octaethylporphyrin) has been prepared from Ru(OEP)(CO)EtOH, and the X-ray crystal structure determined; as expected, the six-coordinate ruthenium is situated in the porphyrin plane and has two axial phosphine ligands. Synthesized also from the carbonyl(ethanol) precursors were the corresponding tris(p-methoxyphenyl)phosphine complex, and the Ru(TPP)L2 (TPP = the dianion of tetraphenylporphyrin, L = PPh3, P(p-CH3OC6H4)3, P″Bu3) and Ru(TPP)(CO)PPh3 complexes. Optical and 1H nmr data are presented for the complexes in solution. In some cases dissociation of a phosphine ligand to generate five-coordinate species occurs and this has been studied quantitatively in toluene at 20 °C for the Ru(OEP)L2 and Ru(TPP)L2 systems.

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