Synthesis and Study of the Structure-Activity Relationship of Antiproliferative N-Substituted Isosteviol-Based 1,3-Aminoalcohols.

ABSTRACT: Starting from isosteviol, a series of diterpenoid 1,3-aminoalcohol derivatives were prepared via stereoselective transformations. The acid-catalysed hydrolysis and rearrangement of natural stevioside produced isosteviol, which was transformed into the key intermediate methyl ester. In the next step, an 1,3-aminoalcohol library was prepared by the reductive amination of the intermediate 3-hydroxyaldehyde obtained from isosteviol in a two-step synthesis. To study the effect of the carboxylate ester function at position 4, the free carboxylic acid, benzyl ester and acryloyl ester analogues were prepared as elongated derivatives in comparison with our earlier results in this field. The antiproliferative activity of compounds against human tumour cell lines (A2780, HeLa, MCF-7 and MDA-MB-231) w

SUBMITTER: Ozsvar D 

PROVIDER: S-EPMC10893060 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature