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| Content Provider | Royal Society of Chemistry (RSC) |
|---|---|
| Author | Rose, Patricia A. Nyangulu, James M. Nelson, Ken M. Gai, Yuanzhu Lougheed, Brenda Quail, J. Wilson Cutler, Adrian J. Abrams, Suzanne R. Loewen, Mary |
| Copyright Year | 2006 |
| Abstract | Bicyclic analogues of the plant hormone abscisic acid (ABA) were designed to incorporate the structural elements and functional groups of the parent molecule that are required for biological activity. The resulting tetralone analogues were predicted to have enhanced biological activity in plants, in part because oxidized products would not cyclize to forms corresponding to the inactive catabolite phaseic acid. The tetralone analogues were synthesized in seven steps from 1-tetralone and a range of analogues were accessible through a second route starting with 2-methyl-1-naphthol. Tetralone ABA 8 was found to have greater activity than ABA in two bioassays. The absolute configuration of (+)-8 was established by X-ray crystallography of a RAMP hydrazone derivative. The hydroxymethyl compounds 10 and 11, analogues for studying the roles of 8′- and 9′-hydroxy ABA 3 and 6, were also synthesized and found to be active. |
| Starting Page | 1400 |
| Ending Page | 1412 |
| Page Count | 13 |
| File Format | HTM / HTML PDF |
| ISSN | 14770520 |
| Volume Number | 4 |
| Issue Number | 7 |
| Journal | Organic & Biomolecular Chemistry |
| DOI | 10.1039/b509193d |
| Language | English |
| Publisher | Royal Society of Chemistry |
| Access Restriction | Open |
| Subject Keyword | ABA Hormone X-ray crystallography 1-Naphthol Carboxylic acid Absolute configuration Eight foot pitch Hydrazone Tetralone |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Biochemistry Physical and Theoretical Chemistry |
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