Synthesis of novel migrastatin and dorrigocin A analogues from D-glucal
Anquetin, G; Rawe, SL; Mcmahon, K; Murphy, EP; Murphy, PV
| HERO ID | 4943269 |
|---|---|
| In Press | No |
| Year | 2008 |
| Title | Synthesis of novel migrastatin and dorrigocin A analogues from D-glucal |
| Authors | Anquetin, G; Rawe, SL; Mcmahon, K; Murphy, EP; Murphy, PV |
| Journal | Chemistry: A European Journal |
| Volume | 14 |
| Issue | 5 |
| Page Numbers | 1592-1600 |
| Abstract | The synthesis of a range of analogues of the migrastatin macrolide core has been achieved from tri-O-acetyl-D-glucal in order to facilitate structure-activity studies. Efficient macrolactone formation was achieved in the presence of a reactive olefin, by increasing steric hindrance in the olefin environment. Acyclic analogues of migrastatin, structurally related to dorrigocin A, have also been prepared from D-glucal. The dorrigocin A analogues were prepared using the combination of the cross metathesis of ethyl 6-heptenoate with a glycal derivative and a subsequent allylic rearrangement-alkene isomerisation reaction (Perlin reaction). A synthetic route is thus provided that will enable dorrigocin A analogues to be prepared in parallel to migrastatin analogues in the search for novel anti-cancer and anti-arthritic therapeutics. Biological evaluation of one migrastatin and one dorrigocin A sugar derived analogue show that they inhibit proliferation and serum-induced migration of tumour and synovial cells at higher concentrations than evodiamine. Dorrigocin A analogues displayed similar potency to analogues of the migrastatin core. |
| Doi | 10.1002/chem.200701033 |
| Pmid | 18038383 |
| Wosid | WOS:000253326200023 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |