Azastene

Azastene

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Names
Other names Win-17625
Identifiers
CAS Number	13074-00-5
ChEMBL	ChEMBL2103987
ChemSpider	9900482
Jmol 3D model	Interactive image
PubChem	11725766
InChI InChI=1S/C23H33NO2/c1-20(2)18-7-6-15-16(21(18,3)12-14-13-24-26-19(14)20)8-10-22(4)17(15)9-11-23(22,5)25/h7,13,15-17,25H,6,8-12H2,1-5H3/t15-,16+,17+,21-,22+,23+/m1/s1 Key: AXLOCHLTNQDFFS-BESJYZOMSA-N
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC=C4[C@@]3(CC5=C(C4(C)C)ON=C5)C
Properties
Chemical formula	C23H33NO2
Molar mass	355.52 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Azastene is a chemical that modulates 3β-hydroxysteroid dehydrogenase activity.

Synthesis

File:Azastene synthesis.png

Azastene synthesis:

One synthesis of this compound involves initial alkylation of methyl testosterone by means of strong base and methyl iodide to afford the 4,4-dimethyl derivative. Formylation with alkoxide and methyl formate leads to the 2-hydroxymethyl derivative. Reaction of this last with hydroxylamine leads to formation of an isoxazole ring. There is then obtained azastene.