farinomalein
{{Chembox
| Name = Farinomalein
| ImageFile =Farinomalein.svg
| ImageSize = 120px
| PIN = 3-[2,5-Dioxo-3-(propan-2-yl)-2,5-dihydro-1H-pyrrol-1-yl]propanoic acid
| OtherNames = 2,5-Dihydro-3-(1-methylethyl)-2,5-dioxo-1H-pyrrole-1-propanoic acid
|Section1={{Chembox Identifiers
| CASNo = 1175521-35-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X32ZX6P3ZV
| PubChem = 44254797
| ChemSpiderID = 24674945
| SMILES = CC(C)C1=CC(=O)N(C1=O)CCC(=O)O
| StdInChI = 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)
| StdInChIKey = UWAZSQUZHSRNTR-UHFFFAOYSA-N
| ChEMBL = 1082049
}}
|Section2={{Chembox Properties
| C=10|H=13|N=1|O=4
| Appearance = White powder
| MeltingPtC = 75 to 77
| SolubleOther = CH2Cl2, acetone, toluene, CH3OH
| VaporPressure = 0 mmHg (25 °C)
}}
|Section7={{Chembox Hazards
| GHSPictograms =
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| HPhrases = {{HPhrases|}}
| PPhrases = {{PPhrases|}}
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Farinomalein is a natural maleimide with formula C10H13NO4 - was first isolated from the entomopathogenic fungus Isaria farinosa (Paecilomyces farinosus) - source H599 (Japan).{{cite journal | doi = 10.1021/np9002806| pmid = 19670877| title = Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus| journal = Journal of Natural Products| volume = 72| issue = 8| pages = 1544–6| year = 2009| last1 = Putri| first1 = Sastia P| last2 = Kinoshita| first2 = Hiroshi| last3 = Ihara| first3 = Fumio| last4 = Igarashi| first4 = Yasuhiro| last5 = Nihira| first5 = Takuya}}
Farinomalein has shown potent and selective inhibition (0.15-5 μg/disk) against eight isolates of plant pathogenic Phytophthora sojae.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. These results suggest that farinomalein might be useful as a candidate pesticide for the treatment of Phytophthora stem rot in soybean.
Synthesis
A simple two-stage synthesis from the γ-hydroxybutenolide compound, 5-hydroxy-4-methyl-2-5(H)-furanone, has been reported.{{cite journal | doi = 10.1016/j.tetlet.2010.01.083| title = Synthesis of farinomalein| journal = Tetrahedron Letters| volume = 51| issue = 13| pages = 1710| year = 2010| last1 = Miles| first1 = William H| last2 = Yan| first2 = Ming}} 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.