Synthesis of potent neuroprotective butenolides based on plant smoke derived 3,4,5-Trimethylfuran-2(5H)-one and 3-methyl-2H-furo[2,3-c]pyrone-2-one
Language English Country England, Great Britain Media print-electronic
Document type Journal Article
PubMed
31014820
DOI
10.1016/j.phytochem.2019.03.014
PII: S0031-9422(18)30798-2
Knihovny.cz E-resources
- Keywords
- Acetylcholinesterase, Karrikinolide, Monoamine oxidase, Smoke, Synthesis, Trimethylbutenolide,
- MeSH
- Acetylcholinesterase metabolism MeSH
- Depressive Disorder drug therapy MeSH
- Furans chemical synthesis chemistry pharmacology MeSH
- 4-Butyrolactone analogs & derivatives chemical synthesis chemistry pharmacology MeSH
- Monoamine Oxidase Inhibitors chemical synthesis chemistry pharmacology MeSH
- Humans MeSH
- Molecular Structure MeSH
- Monoamine Oxidase metabolism MeSH
- Neurodegenerative Diseases drug therapy MeSH
- Neuroprotective Agents chemical synthesis chemistry pharmacology MeSH
- Pyrans chemical synthesis chemistry pharmacology MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- 3-methyl-2H-furo(2,3-c)pyran-2-one MeSH Browser
- 3,4,5-trimethylfuran-2(5H)-one MeSH Browser
- Acetylcholinesterase MeSH
- butenolide MeSH Browser
- Furans MeSH
- 4-Butyrolactone MeSH
- Monoamine Oxidase Inhibitors MeSH
- Monoamine Oxidase MeSH
- Neuroprotective Agents MeSH
- Pyrans MeSH
Smoke derived karrikinolide and trimethylbutenolide exerted neuroprotective effects against monoamine oxidase and acetylcholinesterase. Synthesis of potent analogs was achieved. Sulphur substitution in the bicyclic ring structure of KAR1 displayed the most encouraging activity returning IC50 values of 13.75 ± 0.001 μM and 0.03 ± 0.02 μM for monoamine oxidase A and B and 0.08 ± 0.006 μM for acetylcholinesterase. Neuroprotective butenolides may be particularly useful in the treatment of depressive disorders, Alzheimer's and Parkinson's diseases.
References provided by Crossref.org
Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives
