Article · Wikipedia archive · Last revised Jul 24, 2026

Neoxaline

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. 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."

Last revised
Jul 24, 2026
Read time
≈ 1 min
Length
225 w
Citations
3
Source
Wikipedia ↗
Neoxaline
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Names
IUPAC name
(14E)-11-hydroxy-14-(1H-imidazol-5-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.01,13.03,8]hexadeca-3,5,7-triene-12,15-dione
Other names
Nedoxaline
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • InChI=1S/C23H25N5O4/c1-5-21(2,3)22-11-18(29)20(31)27-17(10-14-12-24-13-25-14)19(30)26-23(22,27)28(32-4)16-9-7-6-8-15(16)22/h5-10,12-13,18,29H,1,11H2,2-4H3,(H,24,25)(H,26,30)/b17-10+
    Key: HHLNXXASUKFCCX-LICLKQGHSA-N
  • 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.12 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

See also

References

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. Bibcode:2013JAChS.13512568I. doi:10.1021/ja406657v. PMID 23957424.