SPF32629A and SPF32629B: Enantioselective synthesis, determination of absolute configuration, cytotoxicity and antibacterial evaluation

We report herein an efficient enantioselective synthesis of SPF32629A and SPF32629B through one-pot enantioselective reduction and protecting-group-free regioselective O-acylation strategy. The absolute configuration of the enantiomerically pure isomers was established by Mosher ester analysis. The inhibitory potencies of the synthesized compounds were assayed in vitro against a panel of microorganisms and against A549 human lung adenocarcinoma cell line. Compounds 2, 11 and 12 displayed moderate to potent antibacterial activity against all the tested strains and compounds 7, 8, 2, 11 and 12 exhibited significant cytotoxicity in a dose-dependent manner with an IC50 values ranging from 2.92 to 4.14 μg/ml and 8–11 μM.

Graphical abstractWe report herein an efficient enantioselective synthesis, absolute configuration elucidation, cytotoxicity and antibacterial evaluation of SPF32629A and SPF32629B, which resulted in the identification of potent antimicrobial and anticancer agents.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► We report the first enantioselective synthesis of SPF32629A and SPF32629B. ► The absolute configuration of SPF32629A and B was established by Mosher ester analysis. ► Synthesized compounds were assayed in vitro for their antimicrobial and cytotoxicity activity. ► Compounds 2, 11 and 12 displayed potent anti-bacterial activity. ► Compounds 7, 8, 2, 11 and 12 displayed significant cytotoxicity in a dose-dependent manner.