Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives.
Article Details
- CitationCopy to clipboard
Secci D, Carradori S, Bolasco A, Chimenti P, Yanez M, Ortuso F, Alcaro S
Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives.
Eur J Med Chem. 2011 Oct;46(10):4846-52. doi: 10.1016/j.ejmech.2011.07.017. Epub 2011 Jul 19.
- PubMed ID
- 21872365 [ View in PubMed]
- Abstract
Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC(50) values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Clorgiline Amine oxidase [flavin-containing] A IC 50 (nM) 4460 N/A N/A Details Iproniazid Amine oxidase [flavin-containing] B IC 50 (nM) 7540 N/A N/A Details Isatin Amine oxidase [flavin-containing] B IC 50 (nM) 18750 N/A N/A Details Moclobemide Amine oxidase [flavin-containing] A IC 50 (nM) 361380 N/A N/A Details Selegiline Amine oxidase [flavin-containing] A IC 50 (nM) 67.25 N/A N/A Details Selegiline Amine oxidase [flavin-containing] B IC 50 (nM) 19.6 N/A N/A Details