期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2017, 期 43, 页码 6408-6412出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701235
关键词
3-Amino cyanoacrylates; Cyanoacrylates; Configuration determination; Isomers; Inhibitors
资金
- Independent Research Fund Denmark\Technology and Production Sciences [4005-00204B]
- Obel foundation
- SparNord foundation
- Carlsberg foundation
- Danish Ministry of Higher Education and Science [AU-2010-612-181]
Potent and selective myosin inhibitors are of vast scientific interest in the development of treatments for diseases involving myosin dysfunction or overactivity. A novel fungicide, ethyl 2-cyano-3-amino-3-phenylacrylate (commercialized as phenamacril), was recently identified as an inhibitor of myosin-5 in F. graminearum. Although the compound has been known since 1900, a general confusion concerning the stereochemical configuration at the exocyclic double bond persists in the literature, thus restricting further drug development of this compound and derivatives. By using NMR and quantum mechanical calculations, this work establishes the stereoconfiguration as the (Z) form and that the effect of a single hydrogen bond is crucial in keeping these types of molecules in a single configuration.
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