dc.contributor.author | Loughlin, Wendy A | |
dc.contributor.author | Schweiker, Stephanie S | |
dc.contributor.author | Jenkins, Ian D | |
dc.contributor.author | Henderson, Luke C | |
dc.date.accessioned | 2017-05-03T12:22:37Z | |
dc.date.available | 2017-05-03T12:22:37Z | |
dc.date.issued | 2013 | |
dc.date.modified | 2014-06-11T03:12:16Z | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.doi | 10.1016/j.tet.2012.12.004 | |
dc.identifier.uri | http://hdl.handle.net/10072/52568 | |
dc.description.abstract | An effective synthesis of 4.5-spiro lactams 28/29, has been completed in nine steps with an overall yield of 5.8%. The 4.5-spiro lactams were made from 2-allyl-Cbz-Pro-OMe 21, which was converted into the corresponding alcohol 22 via a hindered borane reaction with (2-methylbutyl)2borane. Subsequent Swern oxidation of 22 gave novel aldehyde 23. Aldehyde 23 was treated under Bucherer-Bergs reaction conditions to give hydantoin 26, which was opened to the corresponding amino acid 30 using di-tert-butyl dicarbonate and DMAP followed by hydrolysis. Treatment of amino acid 30 with acidic methanol gave 4.5-spiro lactams 28/29. Only 4.5-spiro lactam 29 displayed moderate activity against GPa with an IC50 of 241 卮 | |
dc.description.peerreviewed | Yes | |
dc.description.publicationstatus | Yes | |
dc.format.extent | 352350 bytes | |
dc.format.mimetype | application/pdf | |
dc.language | English | |
dc.language.iso | eng | |
dc.publisher | Elsevier | |
dc.publisher.place | United Kingdom | |
dc.relation.ispartofstudentpublication | N | |
dc.relation.ispartofpagefrom | 1576 | |
dc.relation.ispartofpageto | 1582 | |
dc.relation.ispartofissue | 5 | |
dc.relation.ispartofjournal | Tetrahedron | |
dc.relation.ispartofvolume | 69 | |
dc.rights.retention | Y | |
dc.subject.fieldofresearch | Medicinal and biomolecular chemistry | |
dc.subject.fieldofresearch | Medicinal and biomolecular chemistry not elsewhere classified | |
dc.subject.fieldofresearch | Organic chemistry | |
dc.subject.fieldofresearch | Organic chemical synthesis | |
dc.subject.fieldofresearchcode | 3404 | |
dc.subject.fieldofresearchcode | 340499 | |
dc.subject.fieldofresearchcode | 3405 | |
dc.subject.fieldofresearchcode | 340503 | |
dc.title | Synthesis and evaluation of C8-substituted 4.5-spiro lactams as Glycogen Phosphorylase a inhibitors | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
gro.rights.copyright | © 2013 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version. | |
gro.date.issued | 2013 | |
gro.hasfulltext | Full Text | |
gro.griffith.author | Jenkins, Ian D. | |
gro.griffith.author | Loughlin, Wendy A. | |