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farinomalein : ウィキペディア英語版 | farinomalein
Farinomalein - a natural maleimide with formula C10H13NO4 - was first isolated from the entomopathogenic fungus ''Isaria farinosa'' (''Paecilomyces farinosus'') - source H599 (Japan).〔Sastia P. Putri, Hiroshi Kinoshita, Fumio Ihara, Yasuhiro Igarashi and Takuya Nihira. ''Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus''. J. Nat. Prod., 2009, 72 (8), pp 1544-1546 〕 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.〔William H. Miles and Ming Yan. ''Synthesis of farinomalein''. Tetrahedron Letters, 2010, 51 (13), pp 1710-1712 〕 Firstly, 5-hydroxy-4-methyl-2-5(H)-furanone is oxidised 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.
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