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Farinomalein

Farinomalein
Names
Preferred IUPAC name
3-[2,5-Dioxo-3-(propan-2-yl)-2,5-dihydro-1H-pyrrol-1-yl]propanoic acid
Other names
2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C10H13NO4/c1-6(2)7-5-8(12)11(10(7)15)4-3-9(13)14/h5-6H,3-4H2,1-2H3,(H,13,14)
    Key: UWAZSQUZHSRNTR-UHFFFAOYSA-N
  • CC(C)C1=CC(=O)N(C1=O)CCC(=O)O
Properties
C10H13NO4
Molar mass 211.217 g·mol−1
Appearance White powder
Melting point 75 to 77 °C (167 to 171 °F; 348 to 350 K)
Solubility CH2Cl2, acetone, toluene, CH3OH
Vapor pressure 0 mmHg (25 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Farinomalein is a natural maleimide with formula C10H13NO4 - was first isolated from the entomopathogenic fungus Isaria farinosa (Paecilomyces farinosus) - source H599 (Japan).[1]

Farinomalein has shown potent and selective inhibition (0.15-5 μg/disk) against eight isolates of plant pathogenic Phytophthora sojae.[2] These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of Phytophthora stem rot in soybean.[2]

Synthesis

A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(H)-furanone, has been reported.[3] Firstly, the furanone is oxidized to 3-isopropylfuran-2,5-dione by Dess–Martin periodinane, followed by acetic acid reflux with beta-alanine. The white powdered product has a melting point of 75-77 °C.

References

  1. ^ Putri, Sastia P; Kinoshita, Hiroshi; Ihara, Fumio; Igarashi, Yasuhiro; Nihira, Takuya (2009). "Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus". Journal of Natural Products. 72 (8): 1544–6. doi:10.1021/np9002806. PMID 19670877.
  2. ^ a b Sastia Prama Putri, Hiroshi Kinoshita, Masayasu Kato and Takuya Nihira. Antimicrobial and antioomycete activities of the novel antibiotic farinomalein. Poster Presentation 2P-2124, Annual Conference, The Society for Bioscience and Bioengineering, Japan, 28 October 2010.
  3. ^ Miles, William H; Yan, Ming (2010). "Synthesis of farinomalein". Tetrahedron Letters. 51 (13): 1710. doi:10.1016/j.tetlet.2010.01.083.

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