cortivazol Struktur

Cortivazol

Bezeichnung:Cortivazol

CAS-Nr1110-40-3

Englisch Name:cortivazol

CBNumberCB9922514

SummenformelC32H38N2O5

Molgewicht530.661

MOL-Datei1110-40-3.mol

Synonyma

Cortivazol

Cortivazol physikalisch-chemischer Eigenschaften

Schmelzpunkt	160-165° and 229-230°
alpha	D23 +14° (CHCl3)
Siedepunkt	686.0±55.0 °C(Predicted)
Dichte	1.33±0.1 g/cm3(Predicted)
pka	12.43±0.70(Predicted)

Gefahreninformationscode (GHS)

cortivazol Chemische Eigenschaften,Einsatz,Produktion Methoden

Originator
Diaster,Diamant,France,1972
Verwenden
Glucocorticoid.
Definition
ChEBI: Cortivazol is a steroid. It derives from a hydride of a pregnane.
Manufacturing Process
To a suspension of 25.0 g of 11β,17α,21-trihydroxy-6,16α-dimethyl-4,6- pregnadiene-3,20-dione in 1.5 liters of alcohol-free chloroform cooled to about 5°C in an ice bath is added with constant stirring 750 ml of cold, concentrated hydrochloric acid and then 750 ml of formalin (low in methanol). The mixture is removed from the ice bath and stirred at room temperature for 7 hours.
The layers are separated and the aqueous phase is back-extracted twice with chloroform. The combined organic layers are washed twice with a 5% solution of sodium bicarbonate, and twice with a saturated salt solution. The solution is dried over magnesium sulfate and evaporated to dryness under reduced pressure.The layers are separated and the aqueous phase is back-extracted twice with chloroform. The combined organic layers are washed twice with a 5% solution of sodium bicarbonate, and twice with a saturated salt solution. The solution is dried over magnesium sulfate and evaporated to dryness under reduced pressure.
The residue is triturated with methanol to afford a crystalline solid. This material contains no detectable amount of starting material by paperstrip chromatography but shows two UV absorbing spots near the solvent front (methanol-formamide 2:1 vs benzene-n-hexane 1:1). An aliquot is recrystallized three times from a mixture of benzene and n-hexane to give 17α,20,20,21-bis(methylenedioxy)-11β-hydroxy-6,16α-dimethyl-4,6- pregnadiene-3-one which is used in the subsequent step of the synthesis without further purification. 17α,20,20,21-bis(methylenedioxy)-11β-hydroxy-6,16α-dimethyl-4,6- pregnadiene-3-one (500 mg) is dissolved in 25 cc of benzene and then about 5 cc of benzene is removed by distillation at normal pressure. The resulting solution is cooled to room temperature. Then 0.75 cc of freshly distilled ethyl formate is added. The air in the system is replaced with nitrogen and 150 mg of sodium hydride (as a 57% dispersion in mineral oil) is added. The mixture is stirred under nitrogen at room temperature for three hours. Then 15 cc of a saturated aqueous solution of sodium dihydrogen phosphate is added and the product is extracted into ether
. The ether extracts are extracted with 2 N sodium hydroxide and the sodium hydroxide extracts are acidified with sodium dihydrogen phosphate and extracted again into ether. The ether extract is evaporated to dryness to give about 500 mg of a crude product. From the ether solution there is obtained about 290 mg of yellow crystals, MP 220° to 236°C which is 17α,20,20,21- bis(methylenedioxy)-11β-formyloxy-2-hydroxy-methylene-6,16α-dimethyl-4,6- pregnadiene-3-one. The analytical sample is recrystallized from ethyl acetate and has a melting point of 249° to 255°C, [α]D27 -217°, I R 5.81 and 8.37 μm. From the mother liquor is obtained about 127 mg of 17α,20,20-21- bis(methylenedioxy)-11β-hydroxy-2-hydroxymethylene-6,16α-dimethyl-4,6- pregnadiene-3-one. The analytical sample is recrystallized from ether and has a melting point of 200° to 204°C, [α]D27 -197°, IR 6.05 to 6.2 and 6.4 μ. The 17α,20,20,21-bis(methylenedioxy)-11β-hydroxy-2-hydroxymethylene- 6,16α-dimethyl-4,6-pregnadiene-3-one (1.19 g) is dissolved in 25 cc of ethanol. 300 mg of phenyl hydrazine is added and the mixture is refluxed under nitrogen for one hour. About 25 cc of water is added. The product is then extracted into 150 cc of ether. The extracts are washed with 2N HCl, with saturated sodium bicarbonate, water and saturated sodium chloride solution, and then dried over sodium sulfate and evaporated to dryness to give about 1.2 g of crude product. On crystallization from ether there is obtained as a major component the 17α,20,20,21-bis(methylenedioxy)-11β-hydroxy-6,16α- dimethyl-2'-phenyl-4,6-pregnadieno-[3,2-c] pyrazole.
17α,20,20,21-bis(methylenedioxy)-11β-hydroxy-6,16α-dimethyl-2'-phenyl- 4,6-pregnadieno[3,2-c] pyrazole (430 mg), is heated on a steam bath under nitrogen with 40 cc of a 60% aqueous solution of formic aci
Therapeutic Function
Glucocorticoid

cortivazol Upstream-Materialien And Downstream Produkte

Cortivazol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

1110-40-3, cortivazol Verwandte Suche:

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