Cholesterol-Mimetic Pyrene Probes

Synthesis method for the compounds of formula (I) according to one of claims 1 to 3, characterized in that it comprises the following stages:

• a) reacting the pregnenolone of formula (a) and the pyrene derivative of formula (b) wherein n is an integer from 2 to 10, in particular from 2 to 6, in the presence of EtOK, EtOH, in CH2Cl2 at a temperature between 5° C. and 20° C. and for a duration comprised between 10 and 72 hours, which produces the following compound of formula (1):
• b) reacting the compound of formula (1) obtained in the previous stage in the presence of 1.5 equivalents of Ac2O, 10 mol % of DMAP, 1 equivalent of Et3N, in CH2Cl2 for 3 hours, which produces the following compound of formula (2):
• c) reacting the compound of formula (2) obtained in the previous stage in the presence of 2 equivalents of TiCl4, 1.5 equivalents of Et3SiH, in CH2Cl2 for 45 minutes at ambient temperature, which produces the following compound of formula (3):
• d) reacting the compound of formula (3) obtained in the previous stage in the presence of MeONa, in CH2Cl2 for 4 hours at ambient temperature, leads to the following compound of formula (4):
• e) if appropriate, reacting the compound of formula (4) obtained in the previous stage in the presence of TBDMSCl, imidazole, CH2Cl2 for 12 hours at ambient temperature, which produces the following compound of formula (5):
• f) reacting the compound of formula (5) obtained in the previous stage in the presence of 2 equivalents of CH2=PPh3, in a THF/DMSO mixture, for 12 hours at 75° C., which produces the following compound of formula (6):
• g) reacting the compound of formula (6) obtained in the previous stage in the presence of 5 equivalents of TBAF, in THF, for 12 hours at 65° C., produces the following compound of formula (7):