Studies on long-acting aryl carboxylic acid esters of testosterone

A series of aryl carboxylic acid esters of testosterone have been synthesized as possible agents for long-acting steroid therapy. The solubilities, partition coefficients and hydrolysis rate constants of the compounds have been determined. The results show that the partition coefficients increase with increasing chain length and are in keeping with calculated values. The hydrolysis rates decrease with increasing chain length except for the first member of the series (benzoate ester) which exhibits the slowest rate, possibly due to the hydrolytic attack being hindered by steric and electronic effects.