title: Design, synthesis and fungicidal activity of novel sclerotiorin derivatives.
abstract: Sclerotiorin, a chlorine-containing azaphilone-type natural product, was first isolated from Penicillium sclerotiorum and has been reported to exhibit weak fungicidal activity. Optimization of the substituents at the 3- and 5-positions of the sclerotiorin framework was investigated with the aim of discovering novel fungicides with improved activity. The design of sclerotiorin analogues involved replacing the diene side chain with a phenyl group or an aromatic- or heteroaromatic-containing aliphatic side chain. The designed compounds were synthesized by cycloisomerization and subsequent oxidation of suitable 2-alkynylbenzaldehydes, in which a variety of substituents were introduced using a Sonogashira coupling reaction. The structures of these newly prepared compounds were confirmed by 1H and 13C NMR spectroscopy, HRMS and single-crystal X-ray analysis. The antifungal activity of the synthesized compounds was evaluated against seven phytopathogenic species. Compounds 3, 9g and 9h were found to have a broad spectrum of fungicidal activity, and these structurally simpler products can be recognized as lead compounds for further optimization.
authors: Key Laboratory of Pesticide & Chemical Biology, College of Chemistry, Central China Normal University, Ministry of Education, Wuhan 430079, China.
authors: Long
authors: L
authors: Lin
authors: Nick
authors: N
authors: Mulholland
authors: Shao-Wei
authors: SW
authors: Huang
authors: David
authors: D
authors: Beattie
authors: Dianne
authors: D
authors: Irwin
authors: Yu-Cheng
authors: YC
authors: Gu
authors: John
authors: J
authors: Clough
authors: Qiong-You
authors: QY
authors: Wu
authors: Guang-Fu
authors: GF
authors: Yang
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008958:Models, Molecular; D010407:Penicillium / Q000737:chemistry; D010935:Plant Diseases / Q000382:microbiology*; D010944:Plants / Q000382:microbiology*
chemical_list: D001578:Benzopyrans; D005659:Fungicides, Industrial; C101449:sclerotiorin