Synthesis and anti-HIV activity of oleanolic acid derivatives

Thirteen oleanolic acid derivatives were prepared and evaluated for anti-HIV activity in H9 lymphocytes. Saturating the C(12)-C(13) double bond and converting the C(17)-carboxyl group to an aminomethyl group led to compounds 13-15 and 19-20, respectively, which showed improved anti-HIV activity. Compound 15 was the most potent derivative with EC(50)=0.0039 microg/mL and TI=3570.