Azastene

Azastene
Names
	Other names Win-17625
Identifiers
CAS Number	13074-00-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2103987;
ChemSpider	9900482;
PubChem CID	11725766;
CompTox Dashboard (EPA)	DTXSID801180403 ;
	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	355.522 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

Azastene is a chemical that modulates 3β-hydroxysteroid dehydrogenase activity.^[1]

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.

References

^ Liu, CG; Dai, MZ; Li, WK; Liu, GM; Lin, ZM; Ma, RH (1987). "Interceptive action of azastene and its effects on plasma progesterone in pregnant rats and rabbits". Zhongguo yao li xue bao = Acta pharmacologica Sinica. 8 (6): 540–3. PMID 3451668.
^ Gordon O. Potts, Sterling Drug Inc. U.S. patent 3,966,926 (1976).

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[1] Liu, CG; Dai, MZ; Li, WK; Liu, GM; Lin, ZM; Ma, RH (1987). "Interceptive action of azastene and its effects on plasma progesterone in pregnant rats and rabbits". Zhongguo yao li xue bao = Acta pharmacologica Sinica. 8 (6): 540–3. PMID 3451668.

[2] Gordon O. Potts, Sterling Drug Inc. U.S. patent 3,966,926 (1976).

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