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An Intramolecular Heck Approach To Obtain 17‐Membered Macrocyclic Diversity and the Identification of an Antiangiogenesis Agent from a Zebrafish Assay
Author(s) -
Aeluri Madhu,
Gaddam Jagan,
Trinath Devarakonda V. K. S.,
Chandrasekar Gayathri,
Kitambi Satish Srinivas,
Arya Prabhat
Publication year - 2013
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.201300408
Subject(s) - chemistry , moiety , intramolecular force , stereocenter , stereochemistry , heck reaction , zebrafish , ring (chemistry) , combinatorial chemistry , enantioselective synthesis , biochemistry , organic chemistry , palladium , gene , catalysis
We report a practical and modular approach to obtain two different types of 17‐membered ring macrocyclic compounds through an intramolecular Heck reaction. These macrocyclic compounds are functionalized, that is, they contain two contiguous stereogenic hydroxy functional groups and an amino acid moiety in the macrocyclic ring skeleton. The macrocycles were then screened against a zebrafish assay to determine the antiangiogenesis activity of these small molecules. Macrocyclic compound 2.2a was identified as a potent inhibitor at 2.5 μ M , whereas its acyclic precursor and the other related macrocyclic compounds did not show any effect.