Synthesis and anticonvulsant activity of 4-(2-phenoxyphenyl)semicarbazones

Shafiee, Abbas; Rineh, Ardeshir; Kebriaeezadeh, Abbas; Foroumadi, Alireza; Sheibani, Vahid; Afarinesh, Mohammad Reza

doi:10.1007/s00044-009-9165-0

Cited by 12 publications

(5 citation statements)

References 19 publications

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“…e 1 H NMR and 13 C NMR spectra of the synthesized compounds were recorded in acetone-d 6 and DMSO-d 6 , respectively. In the 1 H NMR spectra of compounds 1-4, the signal of the HC�N proton appeared as a singlet at δ � 8.07-8.23, while the signal of the � N-NH appears as a broad singlet at δ � 9.13-10.04. ese results are similar with the chemical shifts reported for other benzaldehyde and phenoxyphenyl semicarbazone derivatives with the OH, CH 3 , Br, and NO 2 substituents at the phenyl ring [31,35]. e resonance lines of the protons corresponding to the indole ring were observed at δ � 6.83-8.37.…”

Section: Nmr Spectrasupporting

confidence: 87%

Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities

Carrasco-Solís

Hernández-Gorritti

Chupayo

et al. 2020

Journal of Chemistry

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Four indole-3-carbaldehyde semicarbazone derivatives, 2-((5-bromo-1H-indol-3-yl)methylene)hydrazinecarboxamide (1), 2-((5-chloro-1H-indol-3-yl)methylene)hydrazinecarboxamide (2), 2-((5-methoxy-1H-indol-3-yl)methylene)hydrazinecarboxamide (3), and 2-((4-nitro-1H-indol-3-yl)methylene)hydrazinecarboxamide (4) were synthesized and characterized by ESI-MS and spectroscopic (FT-IR, 1H NMR, and 13C NMR) techniques. The two-dimensional NMR (in acetone-d6) spectral data revealed that the molecules 1 and 2 in solution are in the cisE isomeric form. This evidence is supported by DFT calculations at the B3LYP/6-311++G(d,p) level of theory where it was shown that the corresponding most stable conformers of the synthesized compounds have a cisE geometrical configuration, in both the gas and liquid (acetone and DMSO) phases. The in vitro antibacterial activity of compounds 1–4 was determined against Gram-positive (Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Pseudomonas aeruginosa and Escherichia coli) bacteria. Among all the tested semicarbazones, 1 and 2 exhibited similar inhibitory activities against Staphylococcus aureus (MIC = 100 and 150 μg/mL, respectively) and Bacillus subtilis (MIC = 100 and 150 μg/mL, respectively). On the other hand, 3 and 4 were relatively less active against the tested bacterial strains compared with 1, 2, and tetracycline.

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Section: Nmr Spectrasupporting

confidence: 87%

Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities

Carrasco-Solís

Hernández-Gorritti

Chupayo

et al. 2020

Journal of Chemistry

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“…Arylalkylimidazoles [10], semicarbazones [11]a nd thiosemicarbazones [12]werethe compoundswhichattractinterest becauseoftheireasy preparation and good anticonvulsanteffect.The mechanismofactivity of arylsemicarbazonesw asdescribed byblocking of the voltage-gated sodiumi on channels [13].…”

Section: Introductionmentioning

confidence: 99%

“…Inthe lightof previous studies,wep lanned tocondensetwostructuresarylalkylimidazole and (thio)semicarbazone tog ain moree ffectiveanticonvulsantagents. Inthispaper,synthesisand anticonvulsantactivity of some novel 2-(1H -imidazole-1-yl)-1-aryl-substituted ethane-1-one N -substituted phenyl( thio)semicarbazones (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)werestudied.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anticonvulsant evaluation of some novel (thio)semicarbazone derivatives of arylalkylimidazole

Calis

Septioglu²,

Aytemir³

2011

Arzneimittelforschung

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A number of novel 2-(1H-imidazole-1-yl)-1-aryl-substituted ethane-1-one N-substi-tuted phenyl(thio)semicarbazones (1-14) were synthesized to test for their anticonvulsant activity against the two seizure models, maximal electroshock (MES) and subcutaneous pentylenetetrazol (scPTZ). Title compounds were prepared by the reaction of appropriate (thio)semicarba-zides with ketones. Neurotoxicity was screened by the rotarod test. The structure of compounds was confirmed by elemental analysis results and the spectroscopic techniques such as IR, 1H-NMR, 13C-NMR, ESI-MS and HRMS. As a result of activity studies, when the thiosemicar-bazone compounds were compared at different doses, 2-(1H-imidazole-1-yl)-1-(2-naphthyl)ethane-1-one N-(3-chloro-phenyl)thiosemicarbazone (3) and 2-(1H-imidazole-1-yl)-1-(2-biphenyl)ethane-1-one N-(4-fluorophenyl)thiosemicarba-zone (12) were found selective and highly active compounds against MES-induced seizures after 0.5 h and 4 h, respectively. Beside this, 2-(1H-imidazole-1-yl)-1-(1-biphenyl)ethane-1-one N-(4-methylphe-nyl)thiosemicarbazone (14) was the most active compound in the scPTZ-induced seizure test after 4 h. The 2,4-dichloro-phenyl (9) and 2-fluorophenyl (10) substituted biphenyl derivatives of thiosemi-carbazone compounds showed neurotoxicity at higher doses

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“…As a part of our ongoing research program to find novel anti-inflammatory, analgesic, and anticonvulsant compounds, herein, we describe the synthesis and analgesic activity of new analogues of compound 2 by bioisosteric replacement of NH with S and oxidation of S to SO and SO 2 in order to make this moiety as a real hydrogen bond acceptor similar to NH in compound 2 and in the hope of obtaining additional inhibitors of AA metabolism (Almasirad et al, 2005;Almasirad et al, 2006;Rineh et al, 2007;Shafiee et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and analgesic activity of new 1,3,4-oxadiazoles and 1,2,4-triazoles

et al. 2010

Self Cite

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A series of new 1,3,4-oxadiazoles and 1,2,4-triazoles were synthesized in order to obtain new compounds with potential analgesic activity. Compounds were evaluated for their analgesic activities by formalin-induced nociception test. Mefenamic acid (as the reference drug) did not show any activity in the early phase of the formalin test, while compounds 7b, 7c, 8c, and 9a significantly reduced the nociception in this phase. However in the late phase of formalin test all of the target compounds and mefenamic acid showed analgesic activity in comparison to control.

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Synthesis and anticonvulsant activity of 4-(2-phenoxyphenyl)semicarbazones

Cited by 12 publications

References 19 publications

Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities

Indole-3-carbaldehyde Semicarbazone Derivatives: Synthesis, Characterization, and Antibacterial Activities

Synthesis and anticonvulsant evaluation of some novel (thio)semicarbazone derivatives of arylalkylimidazole

Synthesis and analgesic activity of new 1,3,4-oxadiazoles and 1,2,4-triazoles

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