Chemistry:Dysidazirine
From HandWiki
Short description: Natural chemical compound
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| Names | |
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| IUPAC name
Methyl (2S)-3-[(E)-pentadec-1-enyl]-2H-azirine-2-carboxylate
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| Other names
(R)-Dysidazirine; (R)-(-)-dysidazirine
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
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| ChemSpider | |
PubChem CID
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| Properties | |
| C19H33NO2 | |
| Molar mass | 307.478 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 | |
Dysidazirine is a organic compound with formula C19H33NO2. It was discovered as a natural product in 1988 in the marine sponge Dysidea fragilis.[1] Chemically, it is a 2H-azirine derivative.
Dysidazirine synthesis was reported for the first time in 1995.[2]
Dysidazirine kills the yeasts Candida albicans and Sacharamyces cerevisiae in vitro.[3] It also stops HCT-116 human colon cancer cells from growing.[1]
References
- ↑ 1.0 1.1 "Despite my high ring strain, I'm pretty stable. What molecule am I?". American Chemical Society. https://www.acs.org/content/acs/en/molecule-of-the-week/archive/d/r-dysidazirine.html.
- ↑ Davis, Franklin A.; Reddy, G. Venkat; Liu, Hu (1995). "Asymmetric Synthesis of 2H-Azirines: First Enantioselective Synthesis of the Cytotoxic Antibiotic (R)-(-)-Dysidazirine". Journal of the American Chemical Society 117 (12): 3651–3652. doi:10.1021/ja00117a050.
- ↑ Skepper, Colin K.; Dalisay, Doralyn S.; Molinski, Tadeusz F. (2008). "Synthesis and Antifungal Activity of (−)-(Z)-Dysidazirine". Organic Letters 10 (22): 5269–5271. doi:10.1021/ol802065d. PMID 18937483.
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