A series of novel azasterols 8a―8h and 10a―10c were synthesized from the key intermediate 6 by acylation and deprotection.Compound 6 was obtained through a series of reactions including Wittig reaction,etherification,ene reaction,oxidation,oximation and reduction.Structures of the synthesized compounds were confirmed by IR,MS and 1H NMR.Furthermore,all of these compounds were screened for in vitro antiparasitic activity against L.donovani.Among them,compounds 8h,10a and 10b showed a fair inhibition of leishmania promastigotes growth at 25 μg/mL,with potencies close to that of the reference drug,amphotericin B.The results provide a starting point for the development of novel drugs to treat leishmaniasis.
A series of novel 7-amide substituted-4-androstene-3,17-dione derivatives(8αa "8αh or 8βa "8βh) was synthesized from the important intermediates 5 by N-acylation and acidic hydrolysis.Compounds 5α and 5β were obtained through the reaction sequence including acetalization,allylic oxidation,oximation and reduction.The structures of the target compounds were characterized by MS,1H NMR,13C NMR and HRMS spectra and their stereo configurations were identified through DEPT(distortionless enhancement by polarization transfer),HMQC(hetero-nuclear multiple quantum coherence) and NOE(nuclear overhauser effect) correlation.
