Synthesis and Evaluation of Human Monoamine Oxidase Inhibitory Activities of Some 3,5‐Diaryl‐<i>N</i>‐substituted‐4,5‐dihydro‐1<i>H</i>‐pyrazole‐1‐carbothioamide Derivatives

Şentürk, Kerem; Tan, Oya Ünsal; Ciftci, Samiye Yabanoglu; Uçar, Gülberk; Palaska, Erhan

doi:10.1002/ardp.201100448

Cited by 8 publications

(3 citation statements)

References 26 publications

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“…1 H-NMR: δ 3.10 (1H, dd, H A ), 3.18 (3H, s, NH-CH 3 ), 3.78 (1H, dd, H B ), 6.02 (1H, dd, H X ) (J AB : 17.6, J AX : 4.0, J BX : 12.0 Hz), 7.08-7.73 (8H, m, aromatic prot. 3-(4-Fluorophenyl)-5-(4-methylphenyl)-N-methyl-4,5dihydro-1 H -pyrazole-1-carbothioamide (11) Yield: 45.8 %, mp 149 °C. IR (cm − 1 ): 3 362 (N-H), 1 602 (C = N), 1 348 (C 4 -H), 1 320 (C = S), 1 004 (C 5 -N 1 ).…”

Section: -(4-mentioning

confidence: 99%

“…The docking study was performed by using MOE software to understand the orientations of the most active ligand in MAO-A enzyme. The S enantiomer of 9 was preferred for docking studies according to our previous study [ 11 ] . In the binding pose with the lowest energy, it was observed that the 4-Cl phenyl ring at C5 of pyrazole located into the hydrophobic pocket formed by Tyr 444, Tyr 407 and FAD.…”

Section: Molecular Modelingmentioning

confidence: 99%

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Synthesis and Monoamine Oxidase Inhibitory Activities of some 3-(4-Fluorophenyl)-5-aryl-N-substituted-4,5-dihydro-(1H)-pyrazole-1-carbothioamide Derivatives

et al. 2014

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28 new 3-(4-fluorophenyl)-5-aryl-N-substituted-4,5-dihydro-1H-pyrazole-1-carbothioamide derivatives were synthesized and evaluated in vitro for their monoamine oxidase (MAO) A and B inhibitory activity and selectivity. The derivatives substituted by halogen on the fifth position of pyrazole ring, inhibited MAO-A enzyme with a high selectivity index. On the other hand, compounds substituted with 2-naphthyl inhibited MAO-B enzyme with a moderate selectivity index. Docking studies were done to highlight the interactions of the most active derivative with the active site of MAO-A. In addition, in vivo antidepressant and anxiolytic activities of the compounds having selective MAO-A inhibitory effects, were investigated by using Porsolt forced swimming and elevated plus-maze tests respectively. 3-(4-Fluorophenyl)-5-(4-chloro-phenyl)-N-allyl-4,5-dihydro-1H-pyrazole-1-carbothio-amide has antidepressant, 3-(4-fluorophenyl)-5-(4-chlorophenyl)-N-methyl-4,5-dihydro-1H-pyrazole-1-carbothioamide and 3-(4-fluoro-phenyl)-5-(4-bromophenyl)-N-ethyl-4,5-dihydro-1H-pyrazole-1-carbothioamide have anxiolytic activity.

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Section: -(4-mentioning

confidence: 99%

Section: Molecular Modelingmentioning

confidence: 99%

Synthesis and Monoamine Oxidase Inhibitory Activities of some 3-(4-Fluorophenyl)-5-aryl-N-substituted-4,5-dihydro-(1H)-pyrazole-1-carbothioamide Derivatives

et al. 2014

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“…Successively, sixteen new 3-aryl-5-(4-fluorophenyl)-Nsubstituted-4,5-dihydro-1H-pyrazole-1-carbothioamide derivatives were synthesized and their structure were fully characterized as reported in Fig. ( 17) [43]. The compounds were evaluated in vitro for their human monoamine oxidase inhibitory activities and selectivity.…”

Section: Pyrazoline Derivatives As Potent Mao Inhibitorsmentioning

confidence: 99%

Discovery and Optimization of Pyrazoline Derivatives As Promising Monoamine Oxidase Inhibitors

Secci¹,

Carradori²,

Bolasco³

et al. 2012

Current Topics in Medicinal Chemistry

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Among different heterocyclic chemotypes incorporating two nitrogen atoms, pyrazolines could be considered a valid pharmacophore for the synthesis of selective monoamine oxidase (MAO) inhibitors because they were developed by the cyclization of the early hydrazine derivatives such as isocarboxazid. Substituted pyrazolines, decorated with different functional groups, are important lead compounds endowed with a large amount of biological activities. As a matter of this, most of them were also evaluated as dual inhibitors with a synergistic action towards different classes of enzymes (ciclooxygenase, acetylcholinesterase, butyrylcholinesterase). Moreover due to the direct correlation with the recognized MAO inhibition, this scaffold displayed antidepressant and anticonvulsant properties in animal models.

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Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents

Monga

Goyal²,

Steindel

et al. 2013

Med Chem Res

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Synthesis and Evaluation of Human Monoamine Oxidase Inhibitory Activities of Some 3,5‐Diaryl‐N‐substituted‐4,5‐dihydro‐1H‐pyrazole‐1‐carbothioamide Derivatives

Cited by 8 publications

References 26 publications

Synthesis and Monoamine Oxidase Inhibitory Activities of some 3-(4-Fluorophenyl)-5-aryl-N-substituted-4,5-dihydro-(1H)-pyrazole-1-carbothioamide Derivatives

Synthesis and Monoamine Oxidase Inhibitory Activities of some 3-(4-Fluorophenyl)-5-aryl-N-substituted-4,5-dihydro-(1H)-pyrazole-1-carbothioamide Derivatives

Discovery and Optimization of Pyrazoline Derivatives As Promising Monoamine Oxidase Inhibitors

Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents

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