dc.contributor.author |
Radcliff, Fiona |
en |
dc.contributor.author |
Fraser, John |
en |
dc.contributor.author |
Wilson, Zoe |
en |
dc.contributor.author |
Heapy, Amanda |
en |
dc.contributor.author |
Robinson, James |
en |
dc.contributor.author |
Bryant, Christina |
en |
dc.contributor.author |
Flowers, Christopher |
en |
dc.contributor.author |
Brimble, Margaret |
en |
dc.date.accessioned |
2011-09-19T01:34:15Z |
en |
dc.date.issued |
2008 |
en |
dc.identifier.citation |
Bioorg Med Chem 16(11):6179-6185 01 Jun 2008 |
en |
dc.identifier.issn |
0968-0896 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/8057 |
en |
dc.description.abstract |
The naturally occurring phthalide-containing antibiotics spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,015, CJ-13,102, CJ-13,103, CJ-13,104 and CJ-13,108, have been reported to exhibit anti-H. pylori activity. However, the exact stereochemistry of spirolaxine methyl ether, CJ-12,954 or CJ-13,013, contributing to this observed activity has not been confirmed. The anti-H. pylori activity of several analogues of spirolaxine methyl ether, CJ-12,954 and CJ-13,013 of defined stereochemistry together with the anti-H. pylori activity of several indole analogues of the simpler phthalide-containing antibiotics CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015 is reported herein. A 1:1 mixture of spiroacetals 5b and 6b in which the phthalide substituent exhibited (3R)-stereochemistry was sixty times more active than the corresponding 1:1 mixture of spiroacetals with (3S)-stereochemistry. Notably, the unnatural (2″S)-diastereomer of spirolaxine methyl ether exhibited more potent anti-H. pylori activity than the natural product spirolaxine methyl ether. The 4,6-dimethoxyindoles 9, 10, 11 and 13 were all found to be less active than their parent compounds 1, 2, 3 and 4, respectively. Chain-shortened 4,6-dimethoxyindole analogue 12 of CJ-13,108 3 and 4,6-dimethoxyindole-spiroacetal 13 exhibited weak anti-H. pylori activity thus providing future opportunity for drug discovery programs. |
en |
dc.language |
EN |
en |
dc.publisher |
PERGAMON-ELSEVIER SCIENCE LTD |
en |
dc.relation.ispartofseries |
Bioorganic & Medicinal Chemistry |
en |
dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0968-0896/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.subject |
anti-Helicobacter pylori agents |
en |
dc.subject |
phthalide |
en |
dc.subject |
indole |
en |
dc.title |
anti-Helicobacter Pylori Activity of Derivatives of the Phthalide-Containing Antibacterial Agents Spirolaxane Methyl Ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015 |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1016/j.bmc.2008.04.037 |
en |
pubs.issue |
11 |
en |
pubs.begin-page |
6179 |
en |
pubs.volume |
16 |
en |
dc.rights.holder |
Copyright: 2008 Elsevier Ltd. |
en |
dc.identifier.pmid |
18457954 |
en |
pubs.end-page |
6185 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
80843 |
en |
pubs.org-id |
Medical and Health Sciences |
en |
pubs.org-id |
Medical Sciences |
en |
pubs.org-id |
Molecular Medicine |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Chemistry |
en |
pubs.org-id |
Science Research |
en |
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
en |
pubs.record-created-at-source-date |
2010-09-01 |
en |
pubs.dimensions-id |
18457954 |
en |