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Berkelic Acid: Straightforward Analogue Synthesis and Studies of Activity Against Selected Cancer Cell Lines
Author(s) -
Arto Tamara,
de SantaMaría Inés Sáenz,
Chiara MaríaDolores,
Fañanás Francisco J.,
Rodríguez Félix
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601194
Subject(s) - chemistry , natural product , cancer cell lines , combinatorial chemistry , cytotoxicity , secondary metabolite , metabolite , stereochemistry , cell culture , cascade , computational biology , cancer cell , biochemistry , cancer , in vitro , chromatography , medicine , genetics , biology , gene
(–)‐Berkelic acid is an architecturally unique secondary metabolite isolated from an extremophilic Penicillium species. In this paper, we describe a very simple protocol to construct the central core of this natural product. Using this strategy, not only (–)‐berkelic acid, but also a small library of analogues has been accessed. The key point of our protocol is a remarkable silver‐catalysed cascade reaction that allows the assembly of the core of the natural product in a single step and from two simple starting materials, a 4‐pentynol derivative and an ortho ‐alkynylsalicylaldehyde. The cytotoxicity of our synthetic (–)‐berkelic acid and some analogues against two cancer cell lines, OVCAR‐3 and SSCC38, was evaluated.