Synthesis and Evaluation of a 2,11‐Cembranoid‐Inspired Library
نویسندگان
چکیده
The 2,11-cembranoid family of natural products has been used as inspiration for the synthesis of a structurally simplified, functionally diverse library of octahydroisobenzofuran-based compounds designed to augment a typical medicinal chemistry library screen. Ring-closing metathesis, lactonisation and SmI2 -mediated methods were exemplified and applied to the installation of a third ring to mimic the nine-membered ring of the 2,11-cembranoids. The library was assessed for aqueous solubility and permeability, with a chemical-space analysis performed for comparison to the family of cembranoid natural products and a sample set of a screening library. Preliminary investigations in cancer cells showed that the simpler scaffolds could recapitulate the reported anti-migratory activity of the natural products.
منابع مشابه
An Improved Synthesis of 7, 8-Epoxy-1,3,11-cembratriene- 15R(α), 16-diol, a Cembranoid of Marine Origin with a Potent Cancer Chemopreventive Activity
An effective method for the synthesis of 7,8-epoxy-1,3,11-cembratriene15R(α),16-diol and its in vitro Epstein-Barr Virus Early Antigen (EBV-EA) Activation Chemopreventive Assay are reported. This semisynthetic product is a new cembranoid with a potent tumor inhibitory activity that is expected to be a lead compound for a new class of chemopreventive agents of marine origin.
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