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.

References