Synthesis of some novel hydrazone and 2-pyrazoline derivatives: Monoamine oxidase inhibitory activities and docking studies

Evranos-Aksöz, Begüm; Yabanoğlu-Çiftçi, Samiye; Uçar, Gülberk; Yelekçi, Kemal; Ertan, Rahmiye

doi:10.1016/j.bmcl.2014.06.015

Cited by 54 publications

(34 citation statements)

References 27 publications

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“…Recent reports have shown that chalcones are more potent inhibitors of MAO‐A than of MAO‐B. This selectivity may be due to steric hindrance and the nature and orientation of functional groups on the phenyl ring of chalcones . The presence of lipophilic groups such as ethyl, methyl, dimethylamino, bromo, chloro, fluoro, and trifluoromethyl groups at the para position of ring B increases MAO‐B inhibitory activity.…”

Section: Figurementioning

confidence: 78%

Monoamine Oxidase Inhibitory Activity: Methyl‐ versus Chlorochalcone Derivatives

Mathew

Uçar

Mathew³

et al. 2016

ChemMedChem

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Numerous studies have shown that chalcones are promising scaffolds for the development of new monoamine oxidase-B (MAO-B) inhibitors. As a continuation of our ongoing research into the development of reversible human MAO-B (hMAO-B) inhibitors, two series of twenty chalcones containing electron-donating and electron-withdrawing substituents were synthesized. All compounds were found to be competitive, selective, and reversible inhibitors of hMAO-B except (2E)-1-(4-methylphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (P7) and (2E)-1-(4-chlorophenyl)-3-(4-nitrophenyl)prop-2-en-1-one (P17), which were found to be selective inhibitors of hMAO-A. The most potent hMAO-B inhibitor, (2E)-1-(4-chlorophenyl)-3-(4-ethylphenyl)prop-2-en-1-one (P16), showed a K value of 0.11±0.01 μm. Molecular docking simulations were carried out to identify the hypothetical binding mode for the most potent compounds in the active sites of hMAO-A and B. The ability of the compounds to cross the blood-brain barrier was assessed by parallel artificial membrane permeability assay (PAMPA). Additionally, the most potent hMAO-B inhibitor P16 showed no toxicity in cultured hepatic cells at concentrations of 5 and 25 μm.

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Section: Figurementioning

confidence: 78%

Monoamine Oxidase Inhibitory Activity: Methyl‐ versus Chlorochalcone Derivatives

Mathew

Uçar

Mathew³

et al. 2016

ChemMedChem

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“…of two aromatic nucleus of A and B between the open chain of a, b-unsaturated system [7]. The MAO inhibitory activities of chalcones have however, only been determined in a few instances for naturally occurring chalcones using rat, bovine and hamster monoamine oxidases, while some synthetic chalcone derivatives were screened against human MAO (hMAO) [8][9][10][11][12][13][14][15][16]. The gathered results suggested that chalcone derivatives displayed a selective inhibitory activity towards hMAO-B in the micro to nanomolar range.…”

Section: Introductionmentioning

confidence: 99%

Development of fluorinated methoxylated chalcones as selective monoamine oxidase-B inhibitors: Synthesis, biochemistry and molecular docking studies

Mathew

Mathew²,

Uçar

et al. 2015

Bioorganic Chemistry

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“…The ensuing chalcone derivatives 3a-3j were then reacted with hydrazide compounds to furnish hydrazone and 2-pyrazoline derivatives, 5a-5j and 6a-6i (Scheme 1). Synthesis details, physicochemical and spectral characterization of the synthesized compounds have been reported earlier for all compounds except 3i, 3j [29]. The last-mentioned compounds were prepared analogously from acetophenone derivatives and 3-thiophenecarboxaldehyde.…”

Section: Chemistrymentioning

confidence: 99%

Antibacterial, antifungal and antimycobacterial activities of some pyrazoline, hydrazone and chalcone derivatives

Evranos-Aksöz

Onurdağ

Özgacar

2015

Zeitschrift Für Naturforschung C

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Twenty-seven previously reported chalcones and their pyrazoline and hydrazone derivatives as well as two further chalcones have been screened for their antimicrobial, antifungal and antimycobacterial activities against standard microbial strains and drug resistant isolates. The minimum inhibitory concentration (MIC) value of each compound was determined by a two-fold serial microdilution technique. The compounds were found to possess a broad spectrum of antimicrobial activities with MIC values of 8-128 μg/mL. One compound [(E)-1-(4-hydroxyphenyl)-3-p-tolylprop-2-en-1-one] had equal activity with gentamycin (8 μg/mL) against Enterococcus faecalis. Chalcones were found to be more active than their hydrazone and 2-pyrazoline derivatives against Staphylococcus aureus ATCC 29213 and E. faecalis ATCC 29212.

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Synthesis of some novel hydrazone and 2-pyrazoline derivatives: Monoamine oxidase inhibitory activities and docking studies

Cited by 54 publications

References 27 publications

Monoamine Oxidase Inhibitory Activity: Methyl‐ versus Chlorochalcone Derivatives

Monoamine Oxidase Inhibitory Activity: Methyl‐ versus Chlorochalcone Derivatives

Development of fluorinated methoxylated chalcones as selective monoamine oxidase-B inhibitors: Synthesis, biochemistry and molecular docking studies

Antibacterial, antifungal and antimycobacterial activities of some pyrazoline, hydrazone and chalcone derivatives

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