Neoxaline

Neoxaline
Names
Other names
Nedoxaline
Identifiers
3D model (JSmol)
  • CC(C)(C=C)C12CC(C(=O)N\3C1(NC(=O)/C3=C\C4=CN=CN4)N(C5=CC=CC=C25)OC)O
Properties
C23H25N5O4
Molar mass 435.484 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Neoxaline is a bio-active Aspergillus japonicus isolate. It is an antimitotic agent and shows weak inhibitory activity of blood platelet aggregation. It stimulates the central nervous system.[1][2] It has been synthesized through the "highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (−)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline."[3]

See also

References

  1. ^ Neoxaline an antimiotic agent
  2. ^ Hirano, A.; Iwai, Y.; Masuma, R.; Tei, K.; Omura, S. (August 1979). "Neoxaline, a new alkaloid produced by Aspergillus japonicus. Production, isolation and properties". The Journal of Antibiotics. 32 (8): 781–785. doi:10.7164/antibiotics.32.781. PMID 500498.
  3. ^ Ideguchi, Tetsuya; Yamada, Takeshi; Shirahata, Tatsuya; Hirose, Tomoyasu; Sugawara, Akihiro; Kobayashi, Yoshinori; O̅mura, Satoshi; Sunazuka, Toshiaki (19 August 2013). "Asymmetric Total Synthesis of Neoxaline". Journal of the American Chemical Society. 135 (34): 12568–12571. doi:10.1021/ja406657v. PMID 23957424.


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