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Beilstein J. Org. Chem. 2023, 19, 91–99, doi:10.3762/bjoc.19.9
Graphical Abstract
Figure 1: Chemical structure of three isomeric cholesterols.
Figure 2: Selected previously described cholesterol derivatives with interesting antibacterial and cytotoxic ...
Scheme 1: Stereochemical outcome of OH/N3 transformations under different conditions.
Figure 3: Top: cholesterol (1) and the less polar product from the Appel reaction, cholesta-3,5-diene (9); bo...
Figure 4: Top: the more polar product from the Appel reaction 3β-bromocholest-5-ene (4); bottom: X-ray struct...
Figure 5: Top: 3α-azidocholest-5-ene (5) obtained by treatment of 4 with NaN3 in DMF; bottom: X-ray crystal s...
Scheme 2: Mechanistic interpretation of the conversion of cholesterol 1 into diene 9, bromide 4, and azides 5...
Figure 6: Compounds (next to 4, 5 and 9) to be corrected in refs. [10] and [11]. The respective bonds are highlighted...
Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208
Figure 1: Structure of ceragenin (CSA-8) and selected cholesterol conjugates.
Scheme 1: Reagents and conditions: (a) CBr4, PPh3, DCM (74%); (b) NaN3, DMF, 100 °C (63%); (c) CuSO4·5H2O, L-...
Scheme 2: Reagents and conditions: (a) NaN3, DMF, 100 °C (9b, 47%); (b) CuSO4·5H2O, L-AsAc, THF/H2O [11a, n =...
Scheme 3: Reagents and conditions: CuSO4·5H2O, L-AsAc, THF/H2O (96%).
Scheme 4: Reagents and conditions: (a) 1, TMSOTF, CH3CN, rt (74%); (b) NaOMe, MeOH (84%); (c) NaOH; HCl (pH 5...
Scheme 5: Reagents and conditions: (a) 9a, TMSOTF, DCM, rt (19%); (b) 10, CuSO4·5H2O, L-AsAc, THF/H2O (62%); ...
Scheme 6: Reagents & conditions: (a) Propargyl bromide, NaH, Et2O/DMF (quant. for both 26 and 30); (b) 3, CuSO...
Scheme 7: Reagents and conditions: (a) Bu2SnO, MeOH; propargyl bromide, TBAI, Tol (92%); (b) CuSO4·5H2O, L-As...
Figure 2: In vitro antimicrobial activity of some new cholesterol derivatives against E.coli, S. aureus. A. f...
Figure 3: Cytotoxicity effect of some new cholesterol derivatives on the PC3 cell line. Doxorubicin (Dox) was...