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
CAS Number	113507-74-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:185814
ChEMBL	ChEMBL572129
ChemSpider	8742081
PubChem CID	10566693
InChI 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
SMILES CCCCCCCCCCCCCC=CC(=N1)[C@H]1C(=O)OC
Properties
Chemical formula	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

^ ^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.

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