Fluorinated phenylcyclopropylamines. Part 4: effects of aryl substituents and stereochemistry on the inhibition of monoamine oxidases by 1-aryl-2-fluoro-cyclopropylamines.

doi:10.1016/J.BMC.2005.01.043

Paper

DOI: 10.1016/J.BMC.2005.01.043

Fluorinated phenylcyclopropylamines. Part 4: effects of aryl substituents and stereochemistry on the inhibition of monoamine oxidases by 1-aryl-2-fluoro-cyclopropylamines.

Published Apr 1, 2005 · Song Ye, S. Yoshida, R. Fröhlich

Bioorganic & medicinal chemistry

Q2 SJR score

Citations

Influential Citations

Full textSemantic Scholar

Abstract

Abstract hidden due to publisher request; this does not indicate any issues with the research. Click the full text link above to read the abstract and view the original source.

In Vitro Study

Study Snapshot

1-aryl-2-fluorocyclopropylamines are potent and selective inhibitors of MAO A, with both (E)- and (Z)-diastereomers showing equal potency, but no significant inhibition of tyramine oxidase.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Full text analysis coming soon...

References

DOI: 10.1021/JM049957T

Fluorinated phenylcyclopropylamines. 2. Effects of aromatic ring substitution and of absolute configuration on inhibition of microbial tyramine oxidase.

The activity of fluorinated phenylcyclopropylamines as inhibitors of microbial tyramine oxidase is influenced by the nature of para-substituents and absolute configuration, with the (1S,2S)-enantiomer being the most

2004·26citations·Thomas C. Rosen et al.·Journal of medicinal chemistry

Journal of medicinal chemistry

DOI: 10.2174/0929867043364784

Structure and mechanism of monoamine oxidase.

The crystal structure of MAO B reveals a polar nucleophilic mechanism for its catalytic activity, aiding in the development of more effective inhibitors for antidepressants and neuroprotective drugs.

2004·337citations·D. Edmondson et al.·Current medicinal chemistry

Current medicinal chemistry

DOI: 10.1016/J.BMC.2004.03.010

Fluorinated phenylcyclopropylamines. Part 3: Inhibition of monoamine oxidase A and B.

Fluorinated phenylcyclopropylamines show potent inhibitory activity against monoamine oxidase A and B, with some showing selective MAO A inhibition.

2004·51citations·S. Yoshida et al.·Bioorganic & medicinal chemistry

Bioorganic & medicinal chemistry

DOI: 10.1021/JM030398K

Fluorinated phenylcyclopropylamines. 1. Synthesis and effect of fluorine substitution at the cyclopropane ring on inhibition of microbial tyramine oxidase.

Fluorine substitution at the cyclopropane ring increases the inhibitory effect of microbial tyramine oxidase, with trans-2-fluoro-2-phenylcyclopropylamine being the most potent competitive inhibitor.

2004·29citations·S. Yoshida et al.·Journal of medicinal chemistry

Journal of medicinal chemistry

DOI: 10.1006/PREP.2001.1546

High-level expression of human liver monoamine oxidase A in Pichia pastoris: comparison with the enzyme expressed in Saccharomyces cerevisiae.

High-level expression of human MAO-A in Pichia pastoris compared to Saccharomyces cerevisiae results in higher expression levels (329 mg/L) and higher homogeneity of the isolated enzyme.

2002·78citations·Min Li et al.·Protein expression and purification

Protein expression and purification

DOI: 10.1016/S0960-894X(01)00302-X

Inactivation of monoamine oxidase B by 1-phenylcyclopropylamine: mass spectral evidence for the flavin adduct.

1-phenylcyclopropylamine inactivates monoamine oxidase B, producing a flavin adduct structure that can be studied using mass spectrometry.

2001·10citations·Deanna J. Mitchell et al.·Bioorganic & medicinal chemistry letters

Bioorganic & medicinal chemistry letters

DOI: 10.1021/BI010388Q

Spectrometric evidence for the flavin-1-phenylcyclopropylamine inactivator adduct with monoamine oxidase N.

1-PCPA is an inactivator of the fungal monoamine oxidase MAO N, with spectral evidence supporting covalent attachment to the cofactor as N(5)-3-oxo-3-phenylpropyl-FAD.

2001·19citations·D. Mitchell et al.·Biochemistry

Biochemistry

DOI: 10.1107/S0108767390000277

Phase annealing in SHELX-90: direct methods for larger structures

The phase annealing method in SHELX-90 can improve the chances of solving large structures at atomic resolution, potentially increasing the chances of solving crystallographic phase problems.

1990·12814citations·G. Sheldrick·Acta Crystallographica Section A

Acta Crystallographica Section A

Citations

DOI: 10.1021/acs.joc.3c02890

Regio- and Diastereoselective Hydrophosphination and Hydroamidation of gem-Difluorocyclopropenes.

This study demonstrates a mild, transition-metal-free method for producing phosphorus and nitrogen-containing gem-difluorocyclopropanes with excellent regio- and diastereoselectivity, useful for various synthetic applications.

2024·0citations·Yuanshuo Zhang et al.·The Journal of organic chemistry

The Journal of organic chemistry

DOI: 10.3390/molecules27248757

Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids

Carbon monoxide-catalyzed carbonylation of polyfluorinated alcohols and diols produces mono- and dicarboxylic acids or lactones, with FSO3H-SbF5 showing the best results in most transformations.

2022·0citations·Siqi Wang et al.·Molecules

Molecules

DOI: 10.1021/ACSMEDCHEMLETT.0C00220

trans-Fluorine Effect in Cyclopropane: Diastereoselective Synthesis of Fluorocyclopropyl Cabozantinib Analogs.

The fluorocyclopropyl analog of cabozantinib shows improved in vitro profile compared to the parent nonfluorinated structure, offering valuable fine-tuning options for lead optimization in drug discovery.

2020·6citations·Janis Veliks et al.·ACS medicinal chemistry letters

ACS medicinal chemistry letters

DOI: 10.1016/j.bmc.2020.115726

Fluorinated 2-Arylcyclopropan-1-amines - A new class of sigma receptor ligands.

Fluorinated 2-aryl-fluoro-cyclopropan-1-amines show different selectivity for 1 and 2 receptors, with 4-substituted isomers being more active than 3-substituted isomers.

2020·2citations·Benjamin Schinor et al.·Bioorganic & medicinal chemistry

Bioorganic & medicinal chemistry

DOI: 10.1039/c9cc05749h

Fluorine containing cyclopropanes: synthesis of aryl substituted all-cis 1,2,3-trifluorocyclopropanes, a facially polar motif.

Substituted all-cis 1,2,3-trifluorocyclopropanes show potential as a polar, conformationally rigid, and low-log P substituent for pharmaceuticals and agrochemicals research.

2019·14citations·Zeguo Fang et al.·Chemical communications

Chemical communications

DOI: 10.1016/J.JFLUCHEM.2017.09.008

Diastereoselectivity of cyclopropanation of substituted α-fluorostyrenes versus styrenes by different methods

Cyclopropanation of styrene and -fluorostyrenes with diazoacetate yields different diastereoselectivity depending on the catalyst used and the presence or absence of fluorine substituent.

2017·6citations·Katharina Bartels et al.·Journal of Fluorine Chemistry

Journal of Fluorine Chemistry