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Heerdegen, Desiree; Reuter, Doreen; Kornmayer, Moritz M.; Kriegler, Katharina N.; Müller, Christoph; Mayer, Peter; Bracher, Franz (2020): Synthesis ofSeco-Analogues of the DHCR24 Inhibitor SH-42. In: European Journal of Organic Chemistry, Vol. 2020, No. 39: pp. 6270-6288
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In a project aimed at the further development of the potent steroidal anti-inflammatory Delta(24)-dehydrocholesterol reductase (DHCR24) inhibitor SH-42 we worked out routes to ring B seco-steroidal analogues. The required building blocks, bearing rings C and D of the parent steroidal structure, were synthesised starting from ergocalciferol. The novelseco-analogues carry aromatic residues as ring A equivalents at C-4 position with variation of the linker length resulting in 4-aryl-, 4-benzyl- and 4-(arylethyl)perhydroindanes. As saturated analogues of the latter 4-(cyclohexylethyl)perhydroindanes were prepared. Moreover, aromatic and aliphatic residues were attached to C-5 position of the perhydroindane scaffold. Unfortunately, none of these structurally diverseseco-analogues of SH-42 showed noteworthy inhibition of target enzyme DHCR24, indicating the relevance of the intact steroidal structure for the development of potent inhibitors of this enzyme.