Selective Inhibitors of Monoamine Oxidase. 2. Arylamide SAR

Harfenist, M.; Joyner, Charles T.; Mize, Patrick D.; White, Helen L.

doi:10.1021/jm00039a021

Cited by 26 publications

(18 citation statements)

References 1 publication

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“…The pharmacophore model included four features: two hydrophobic (aromatic rings), one donor atom (nitrogen in the pyrrole) and one acceptor atom (substituent in the nitrogen of the pyrrole). This data is consistent with previous publications where aromatic rings were important elements in the MAO inhibitors structure [120,121]. According to the QSAR model for MAO-A inhibitors, steric fields near the aromatic substituents in C 2 of the indole could increase the activity (Fig.…”

Section: D Qsar Comfa Modelssupporting

confidence: 92%

“…8). The dataset of 65 compounds previously published [121,147,148] was divided in training set (52 compounds were used to generate the pharmacophoric model) and test set (13 compounds). Pharmacophore modeling was developed with the help of Maestro software [149] through Phase module [150] that combines conformational sampling with different scoring methods to identify pharmacophoric hypothesis.…”

Section: D Pharmacophoric Modelsmentioning

confidence: 99%

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Predicting Monoamine Oxidase Inhibitory Activity Through Ligand-Based Models

Vilar¹,

Ferino²,

Quezada³

et al. 2013

CTMC

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The evolution of bio-and cheminformatics associated with the development of specialized software and increasing computer power has produced a great interest in theoretical in silico methods applied in drug rational design. These techniques apply the concept that "similar molecules have similar biological properties" that has been exploited in Medicinal Chemistry for years to design new molecules with desirable pharmacological profiles. Ligand-based methods are not dependent on receptor structural data and take into account two and three-dimensional molecular properties to assess similarity of new compounds in regards to the set of molecules with the biological property under study. Depending on the complexity of the calculation, there are different types of ligand-based methods, such as QSAR (Quantitative Structure-Activity Relationship) with 2D and 3D descriptors, CoMFA (Comparative Molecular Field Analysis) or pharmacophoric approaches. This work provides a description of a series of ligand-based models applied in the prediction of the inhibitory activity of monoamine oxidase (MAO) enzymes. The controlled regulation of the enzymes' function through the use of MAO inhibitors is used as a treatment in many psychiatric and neurological disorders, such as depression, anxiety, Alzheimer's and Parkinson's disease. For this reason, multiple scaffolds, such as substituted coumarins, indolylmethylamine or pyridazine derivatives were synthesized and assayed toward MAO-A and MAO-B inhibition. Our intention is to focus on the description of ligand-based models to provide new insights in the relationship between the MAO inhibitory activity and the molecular structure of the different inhibitors, and further study enzyme selectivity and possible mechanisms of action.

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Section: D Qsar Comfa Modelssupporting

confidence: 92%

Section: D Pharmacophoric Modelsmentioning

confidence: 99%

Predicting Monoamine Oxidase Inhibitory Activity Through Ligand-Based Models

Vilar¹,

Ferino²,

Quezada³

et al. 2013

CTMC

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“…[12][13][14][15][16][17] In a previous paper we have described the synthesis and properties of fluorescent 2-(α-aryloxyacetyl)-phenoxathiin derivatives on treating alkali aroxides with 2-(α-bromoacetyl)-phenoxathiin (3) in the presence of crown ethers.…”

Section: Introductionmentioning

confidence: 99%

Reaction of 2-(α-bromoacetyl)-phenoxathiin with substituted o-, m-, or p-formyl-aroxides

Radutiu¹,

Baciu²,

Cãproiu³

et al. 2007

Arkivoc

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Solid sodium-or potassium aroxides with formyl and alkoxy substituents were reacted with 2-(α-bromoacetyl)-phenoxathiin 3 in the presence of crown ethers (15C5 or 18C6, respectively). When the formyl and hydroxy groups were in meta-or para-positions the resulting fluorescent compounds were 2-(α-formylaryloxyacetyl)-phenoxathiins 4a-d; however, when these substituents were in the ortho position, the fluorescent products were benzo[b]furyl 2-phenoxathiinyl ketones 5e-h, or naphtho[3,2-b]furyl 2-phenoxathiinyl ketone 8. The chromatographic behavior of compounds 4a-d, 5e-h, and 8 was investigated by TLC and reverse-phase-TLC (RP-TLC) for the hydrophobicity properties.

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“…This observation prompted us to synthesise some new aryl amides (6,7), sulphonamides (8,9) and 5-oxo-imidazolines (10,11) derivatives bearing benzimidazole moiety, with a view to studying their pharmacological profile. This observation prompted us to synthesise some new aryl amides (6,7), sulphonamides (8,9) and 5-oxo-imidazolines (10,11) derivatives bearing benzimidazole moiety, with a view to studying their pharmacological profile.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Arylamides, Sulphonamides and 5-Oxo-Imidazolines as Novel Bioactive Compounds Derived From Benzimidazole

Kagthara¹,

Shah²,

Doshi³

et al. 1998

Heterocyclic Communications

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A number of new arylamides (2a-o), sulphonamides (3a-p) and 5-oxo imidazolines (4a-o) have been synthesised by the condensation of acid hydrazide of o-benzoylene-2,1-benzimidazole 1 with different aromatic acid chlorides, aryl carboxy sulphonylchlorides and azlactones in dry pyridine. All the productswere evaluated invitro for their antimicrobial activity against several microbes and antitubercular activity against Mycobacterium tuberculosis H37Rv.

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Selective Inhibitors of Monoamine Oxidase. 2. Arylamide SAR

Cited by 26 publications

References 1 publication

Predicting Monoamine Oxidase Inhibitory Activity Through Ligand-Based Models

Predicting Monoamine Oxidase Inhibitory Activity Through Ligand-Based Models

Reaction of 2-(α-bromoacetyl)-phenoxathiin with substituted o-, m-, or p-formyl-aroxides

Synthesis of Some Arylamides, Sulphonamides and 5-Oxo-Imidazolines as Novel Bioactive Compounds Derived From Benzimidazole

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