Dysidazirine
Appearance
![]() | |
Names | |
---|---|
IUPAC name
Methyl (2S)-3-[(E)-pentadec-1-enyl]-2H-azirine-2-carboxylate
| |
Other names
(R)-Dysidazirine; (R)-(-)-dysidazirine
| |
Identifiers | |
3D model (JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem CID
|
|
| |
| |
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).
|
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
[edit]- ^ a b "Despite my high ring strain, I'm pretty stable. What molecule am I?". ACS.org. American Chemical Society. Retrieved 18 November 2022.
- ^ 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. PMC 2635126. PMID 18937483.