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Synthesis of a Focused Chemical Library Based on Derivatives of Embelin, a Natural Product with Proapoptotic and Anticancer Properties
Author(s) -
Viault Guillaume,
Grée Danielle,
Das Saibal,
Yadav Jhillu Singh,
Grée René
Publication year - 2011
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.201001627
Subject(s) - chemistry , xiap , natural product , combinatorial chemistry , flexibility (engineering) , molecule , small molecule , benzoquinone , stereochemistry , organic chemistry , apoptosis , biochemistry , caspase , statistics , mathematics , programmed cell death
The synthesis of new derivatives of embelin, a natural inhibitor of X‐linked inhibitor of apoptosis protein (XIAP) is described. The design of these new molecules involved introduction of aromatic groups directly linked to the benzoquinone core. To allow a large flexibility in the nature and the length of the added chain, the strategy involves first aSuzuki–Miyaura reaction with functionalized aromatics, yielding a first generation of molecules. Then, by appropriate use of the functional groups, a second generation of representative embelin derivatives was prepared.