Dysidazirine

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
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
  • InChI=1S/C19H33NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(20-17)19(21)22-2/h15-16,18H,3-14H2,1-2H3/b16-15+/t18-/m0/s1
    Key: UOLCWKPNWDZCIP-ZPICJPFVSA-N
  • CCCCCCCCCCCCCC=CC(=N1)[C@H]1C(=O)OC
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 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. "Despite my high ring strain, I'm pretty stable. What molecule am I?". ACS.org. American Chemical Society. Retrieved 18 November 2022.
  2. 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.
  3. 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.