Neoxaline

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| ImageFile = Neoxaline.svg

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| IUPACName = (14E)-11-hydroxy-14-(1H-imidazol-5-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.0^1,13.0^3,8]hexadeca-3,5,7-triene-12,15-dione

| OtherNames = Nedoxaline

|Section1={{Chembox Identifiers

| CASNo = 71812-10-7

| ChemSpiderID = 4944751

| KEGG = C22172

| PubChem = 6440491

| StdInChI=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+

| StdInChIKey = HHLNXXASUKFCCX-LICLKQGHSA-N

| SMILES = CC(C)(C=C)C12CC(C(=O)N\3C1(NC(=O)/C3=C\C4=CN=CN4)N(C5=CC=CC=C25)OC)O

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|Section2={{Chembox Properties

| C=23 | H=25 | N=5 | O=4

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|Section3={{Chembox Hazards

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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.[http://biolinks.co.jp/pdf/Neoxaline.pdf Neoxaline an antimiotic agent]{{cite journal |last1=Hirano |first1=A. |last2=Iwai |first2=Y. |last3=Masuma |first3=R. |last4=Tei |first4=K. |last5=Omura |first5=S. |title=Neoxaline, a new alkaloid produced by Aspergillus japonicus. Production, isolation and properties. |journal=The Journal of Antibiotics |date=August 1979 |volume=32 |issue=8 |pages=781–785 |doi=10.7164/antibiotics.32.781 |pmid=500498|doi-access=free }} 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."{{cite journal |last1=Ideguchi |first1=Tetsuya |last2=Yamada |first2=Takeshi |last3=Shirahata |first3=Tatsuya |last4=Hirose |first4=Tomoyasu |last5=Sugawara |first5=Akihiro |last6=Kobayashi |first6=Yoshinori |last7=O̅mura |first7=Satoshi |last8=Sunazuka |first8=Toshiaki |title=Asymmetric Total Synthesis of Neoxaline |journal=Journal of the American Chemical Society |date=19 August 2013 |volume=135 |issue=34 |pages=12568–12571 |doi=10.1021/ja406657v |pmid=23957424|bibcode=2013JAChS.13512568I }}