7753-60-8 Usage
Description
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.
Chemical Properties
Off-White Solid
Uses
As an angiostatic steroid, Anecortave Acetate can be used in treatment of macular degeneration.
Synthesis
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.
Enzyme inhibitor
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.
Check Digit Verification of cas no
The CAS Registry Mumber 7753-60-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,7,5 and 3 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 7753-60:
(6*7)+(5*7)+(4*5)+(3*3)+(2*6)+(1*0)=118
118 % 10 = 8
So 7753-60-8 is a valid CAS Registry Number.
InChI:InChI=1/C23H30O5/c1-14(24)28-13-20(26)23(27)11-8-19-17-5-4-15-12-16(25)6-9-21(15,2)18(17)7-10-22(19,23)3/h7,12,17,19,27H,4-6,8-11,13H2,1-3H3/t17-,19+,21+,22+,23+/m1/s1
7753-60-8Relevant articles and documents
Graber et al.
, p. 4722 (1953)
Non-hormonal steroid modulators of NF-κβ for treatment of disease
-
Page/Page column 38-39, (2019/11/18)
The present invention relates to compounds and methods which may be useful as treatments of diseases.
Anecortave acetate preparation method
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Paragraph 0032; 0034; 0038; 0039; 0041; 0045; 0048; 0050, (2018/07/30)
The invention discloses an anecortave acetate preparation method which includes, in protection of nitrogen gas, suspending 17-hydroxy-4,9(11)-diene-3,20-diketone-21-halide in a specific solvent, carrying out substitution reaction on presence of acetate and a phase transfer catalyst, and carrying out elutriation and solvent refining to obtain anecortave acetate. With the phase transfer catalyst, reaction time of the conventional process is shortened, and production cost is lowered. Besides, the anecortave acetate preparation method achieves high reaction yield, needs mild reaction condition, has high operability, and is a convenient industrial preparation process.
