Synthesis and Stability Studies of a Simplified, Thiazole-Containing Macrocycle of the Anticancer Agent Salarin C.

ABSTRACT: While salarin C (SalaC) is a potent marine cytotoxin, Kashman demonstrated that congeners which had undergone Wasserman rearrangement exhibit little to no cytotoxicity. Given that thiazoles are known to undergo Wasserman rearrangement at a significantly reduced rate, we hypothesized that a thiazole-containing SalaC would exhibit greater stability without significantly altering the macrocyclic conformation. Herein, we describe the synthesis of a simplified, thiazole-containing macrocycle which demonstrates significantly improved stability under identical aerobic conditions.

SUBMITTER: Woods JE 

PROVIDER: S-EPMC9746118 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature