516-37-0Relevant articles and documents
Oxidation products of ergosterin. 1. Chromatographic separation of oxidation products, isolation of new radiation products of ergosterin under the influence of oxygen
Fürst
, p. 795 - 804 (1965)
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Fieser et al.
, p. 4066,4070 (1953)
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Discoveries and Challenges en Route to Swinhoeisterol A
Duecker, Fenja L.,Heinze, Robert C.,Steinhauer, Simon,Heretsch, Philipp
, p. 9971 - 9981 (2020/07/06)
In this work, a full account of the authors’ synthetic studies is reported that culminated in the first synthesis of 13(14→8),14(8→7)diabeo-steroid swinhoeisterol A as well as the related dankasterones A and B, 13(14→8)abeo-steroids, and periconiastone A, a 13(14→8)abeo-4,14-cyclo-steroid. Experiments are described in detail that provided further insight into the mechanism of the switchable radical framework reconstruction approach. By discussing failed strategies and tactics towards swinhoeisterol A, the successful route that also allowed an access to structurally closely related analogues, such as Δ22-24-epi-swinhoeisterol A, is eventually presented.
Synthesis and bioevaluation of Δ7-5-desaturase inhibitors, an enzyme late in the biosynthesis of the fungal sterol ergosterol
Goldstein, Alex S.
, p. 5092 - 5099 (2007/10/03)
Ergosterol, the predominant sterol of fungi, is postulated to have many cellular functions which include a bulk membrane role and a regulatory role. Studies with sterol auxotrophs show that, even in the presence of sterols which can fulfill the bulk membrane requirements, a small concentration of ergosterol is absolutely necessary for growth. The Δ5-double bond appears to be required for the regulatory role of ergosterol; therefore, development of inhibitors of the enzyme that introduce this double bond, Δ7-sterol 5- desaturase (5-desaturase), may lead to effective antifungal agents. Within is the first reported synthesis of inhibitors of fungal 5-desaturase and the development of an in vitro tritium efficacy radioassay. The inhibitors were of the general structure 7,22(E)-ergostadien-3β-ol with α-face heteroatom substituents in the vicinity of C-5. They exhibited IC50 values of 47-149 μM.