Chemistry:Aurantiamine
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-Aurantiamine.png)
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| Names | |
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| Preferred IUPAC name
(3Z,6S)-3-{[5-(2-Methylbut-3-en-2-yl)-1H-imidazol-4-yl]methylidene}-6-(propan-2-yl)piperazine-2,5-dione | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C16H22N4O2 | |
| Molar mass | 302.378 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
(−)-Aurantiamine is a blue fluorescence metabolite produced by the fungus Penicillium aurantiogriseum, the most common fungi found in cereals.[2] (−)-Aurantiamine belongs to a class of naturally occurring 2,5-diketopiperazines featuring a dehydrohistidine residue that exhibit important biological activities, such as anti-cancer or neurotoxic effects.[3] It is the isopropyl analog of the microtubule binding agent (−)-phenylahistin but is 40 times less active than the latter on P388 cell proliferation.[4] The total asymmetric synthesis of (−)-aurantiamine has been described.[5]
References
- ↑ "KNApSAcK Metabolite Information - C00011252". http://www.knapsackfamily.com/knapsack_core/information.php?word=C00011252.
- ↑ "Terverticillate penicillia: chemotaxonomy and mycotoxin production.". Mycologia 81 (6): 837–861. 1989. doi:10.2307/3760103.
- ↑ Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
- ↑ "Aurantiamine, a diketopiperazine from two varieties of Penicillium aurantiogriseum". Phytochemistry 31 (5): 1613–1615. 1992. doi:10.1016/0031-9422(92)83116-G.
- ↑ "Total asymmetric synthesis of (–)-Phenylhistine, (–)-Aurantiamine and related compounds. Part I". Molecular Diversity 9 (1–3): 99–109. 2005. doi:10.1007/s11030-005-1294-x. PMID 15789557.
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