Synthesis of potential pregnenolone and progesterone spin probes for biomembranes and immunoassays

Article abstract of DOI:10.1016/S0040-4020(98)01187-9

The synthesis and characterization of four new steroidal spin labels, viz., 3'-[[(pregn-5-en-3β-ol-20S-yl)methyl]oate]-2',2',5',5'- tetramethylpyrrolidine-1'-oxyl,3'-[[(pregn-4-en-3-one-20S-yl)methyl]oate]- 2',2',5',5'-tetra methyl pyrrolidine-1'-oxyl, 3'-[(3β-acetoxypregn-5-en-20- one-16α-yl)prop-2'ξ-ol-3'ξ-oate]-2',2',5',5'-tetramethyl pyrrolidine-1_- oxyl and 3_-[(pregn-5-en-3,20-dione-16α-yl)prop-2'ξ-ol-3'ξ-oate]- 2',2',5',5'-tetramethylpyrrolidine-1'-oxyl has been described which involves functionalization of the parent hormone at C-20 and C-16. The key step to all the products was the condensation of 3-carboxyproxyl with the derivatized synthons.