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Synthesis of Novel Macrolactam and Macroketone Analogues of Migrastatin from D ‐Glucal and Comparison with Macrolactone and Acyclic Analogues: A Dorrigocin A Congener Is a Potent Inhibitor of Gastric Cancer Cell Migration
Author(s) -
Anquetin Guillaume,
Horgan Gareth,
Rawe Sarah,
Murray David,
Madden Aideen,
MacMathuna Padraic,
Doran Peter,
Murphy Paul V.
Publication year - 2008
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.200701192
Subject(s) - chemistry , stereochemistry , metathesis , glucal , congener , pharmacology , biochemistry , organic chemistry , catalysis , polymer , polymerization , medicine
Novel macrolactam and macroketone analogues of the migrastatin macrolide core have been synthesised from tri‐ O ‐acetyl‐ D ‐glucal in order to facilitate structure‐activity studies. The Horner olefination, followed by ring‐closing metathesis were key steps in the synthesis of the macroketone. The ability of the macroketone and macrolactam derivatives to inhibit the migration of gastric tumour cells as determined using a transwell migration assay were compared with macrolactone analogues and dorrigocin A analogues. One dorrigocin A congener was the most potent inhibitor of gastric cancer cell migration.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)