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
Anquetin, G; Horgan, G; Rawe, S; Murray, D; Madden, A; Macmathuna, P; Doran, P; Murphy, PV
| HERO ID | 4947771 |
|---|---|
| In Press | No |
| Year | 2008 |
| Title | 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 |
| Authors | Anquetin, G; Horgan, G; Rawe, S; Murray, D; Madden, A; Macmathuna, P; Doran, P; Murphy, PV |
| Journal | European Journal of Organic Chemistry |
| Issue | 11 |
| Page Numbers | 1953-1958 |
| Abstract | 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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008). |
| Doi | 10.1002/ejoc.200701192 |
| Wosid | WOS:000255144100013 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | carbohydrates; tumour cell migration inhibitor; cancer; Horner olefination; migrastatin; dorrigocin A natural products |