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An Array of Bengamide E Analogues Modified at the Terminal Olefinic Position: Synthesis and Antitumor Properties
Author(s) -
MartínGálvez Francisca,
GarcíaRuiz Cristina,
SánchezRuiz Antonio,
Valeriote Frederick A.,
Sarabia Francisco
Publication year - 2013
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201300033
Subject(s) - natural product , stereochemistry , chemistry , terminal (telecommunication) , total synthesis , structure–activity relationship , potency , biological activity , position (finance) , combinatorial chemistry , computational biology , biochemistry , biology , in vitro , computer science , telecommunications , finance , economics
Based on our previously described synthetic strategy for bengamide E, a natural product of marine origin with antitumor activity, a small library of analogues modified at the terminal olefinic position was generated with the objective of investigating the effect of structural modifications on antitumor properties. Biological evaluation of these analogues, consisting of IC 50 determinations against various tumor cell lines, revealed important aspects with respect to the structural requirements of this olefinic position for activity. Interestingly, the analogue possessing a cyclopentyl group displayed greater potency than the parent bengamide E, representing a key finding upon which to base further investigations into the design of new analogues with promising biological activities.