Abstract
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.
Item Type: | Journal article |
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Faculties: | Chemistry and Pharmacy > Department of Pharmacy |
Subjects: | 500 Science > 540 Chemistry |
ISSN: | 1434-193X |
Language: | English |
Item ID: | 89777 |
Date Deposited: | 25. Jan 2022, 09:32 |
Last Modified: | 25. Jan 2022, 09:32 |