Anecortave Acetate Struktur

17-α,21-Dihydroxypregna-4,9(11)-dien-3,20-dion-21-acetat

Bezeichnung:17-α,21-Dihydroxypregna-4,9(11)-dien-3,20-dion-21-acetat

CAS-Nr7753-60-8

Englisch Name:Anecortave Acetate

CBNumberCB5501441

SummenformelC23H30O5

Molgewicht386.48

MOL-Datei7753-60-8.mol

Synonyma

17-α,21-Dihydroxypregna-4,9(11)-dien-3,20-dion-21-acetat

17-α,21-Dihydroxypregna-4,9(11)-dien-3,20-dion-21-acetat physikalisch-chemischer Eigenschaften

Schmelzpunkt	230-234°C
alpha	D +117° (c = 1.0 in CHCl3); D22 +124° (c = 1.04 in CHCl3).
Siedepunkt	551.8±50.0 °C(Predicted)
Dichte	1.23±0.1 g/cm3(Predicted)
storage temp.	-20°C Freezer
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	12.47±0.60(Predicted)
Farbe	Off-White to Beige

Anecortave Acetate Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Anecortave acetate, an angiogenesis inhibitor, was launched in Australia by Alcon for the treatment of age-related macular degeneration (AMD). AMD is the leading cause of untreatable blindness among people aged 65 to 74 years in the U.S. Worldwide, approximately 20 to 25 million people suffer from AMD, a disease that until recently was untreatable. Anecortave, an angiostatic steroid, down-regulates the expression MMP-2 and -9 to exert its antiangiogenic effects.
Chemische Eigenschaften
Off-White Solid
Verwenden
As an angiostatic steroid, Anecortave Acetate can be used in treatment of macular degeneration.
Definition
ChEBI: Anecortave acetate is an organic molecular entity.
Synthese
Anecortave has been synthesized by several different routes, and Pharmacia process patents are cited here. The synthesis is depicted in the scheme. Compound 1 was condensed with 2-chlorovinyl ethyl ether with n-BuLi in THF at low temperature to give a mixture of two isomeric aldehydes 2 in 91% yield. The mixture 2 was treated with acetic anhydride and anhydrous potassium acetate in DMF at 106??C to give acetate 3 which was reacted with RhCl(PPh3)3 and triethylsilane in methylene chloride at 45??C for 4 hours to yield the corresponding triethylsilane ether 4 as a solid after crystallization in hexane. Finally, compound 4 was oxidized with 40% peracetic acid in toluene at low temperature, and the reaction was quenched with SO2 in methanol (2M), and treated with TEA to give anecortave acetate
.
Enzyminhibitor
This novel angiogenesis pro-drug (FW = 386.48 g/mol; CAS 7753-60-8) is taken up and metabolically de-esterified to form the aqnecortave, a synthetic steroid that suppresses the development and elongation of neovascular sprouts and tip cell motility in a VEGF-treated retinal explant model in a dose-dependent manner. Whether used as monotherapy or in combination with sub-therapeutic doses of cisplatin, anecortave acetate significantly controlled tumor burden in a murine retinoblastoma model.

Anecortave Acetate Upstream-Materialien And Downstream Produkte

17-α,21-Dihydroxypregna-4,9(11)-dien-3,20-dion-21-acetat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

7753-60-8, Anecortave Acetate Verwandte Suche:

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