title: Synthesis and fungistatic activity of bicyclic lactones and lactams against Botrytis cinerea, Penicillium citrinum, and Aspergillus glaucus.
abstract: Six analogues of natural trans-4-butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and three derivatives, 11, 12, and 13, of Vince lactam (10) were synthesized and tested as fungistatic agents against Botrytis cinerea AM235, Penicillium citrinum AM354, and six strains of Aspergillus. Moreover, bioresolution carried out by means of whole cell microorganisms and commercially available enzymes afforded opposite enantiomerically enriched (-) and (+) isomers of Vince lactam (10), respectively. The effect of compound structures and stereogenic centers on biological activity has been discussed. The highest fungistatic activity was observed for four lactones: 3, 4, 7, and 8 (IC50 = 104.6-115.2 μg/mL) toward B. cinerea AM235. cis-5,6-Epoxy-2-aza[2.2.1]heptan-3-one (13) indicated significant fungistatic activity (IC50 = 107.1 μg/mL) against Aspergillus glaucus AM211. trans-4-Butyl-cis-3-oxabicyclo[4.3.0]nonan-2-one (3) and trans-4-butyl-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (7) exhibited high fungistatic activity (IC50 = 143.2 and 110.2 μg/mL, respectively) against P. citrinum AM354 as well.
authors.affiliation: Department of Chemistry, Wrocław University of Environmental and Life Sciences , Norwida 25, 50-375 Wrocław, Poland.
authors.forename: Paulina
authors.initials: P
authors.lastname: Walczak
authors.forename: Jakub
authors.initials: J
authors.lastname: Pannek
authors.forename: Filip
authors.initials: F
authors.lastname: Boratyński
authors.forename: Agata
authors.initials: A
authors.lastname: Janik-Polanowicz
authors.forename: Teresa
authors.initials: T
authors.lastname: Olejniczak
mesh_terms: D001230:Aspergillus / Q000187:drug effects*; D020171:Botrytis / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010407:Penicillium / Q000187:drug effects*
chemical_list: D005659:Fungicides, Industrial; D007769:Lactams; D007783:Lactones