1477-19-6 Usage
Description
Benzarone, also known by its brand names Benzarin, Fragivix (r) forte, and Vasco, is a pale yellow solid with multifunctional properties. It is an EYA (Eyes Absents) protein inhibitor, which plays a significant role in organogenesis and has been identified as a potent anticancer agent. Benzarone is particularly effective against ovarian and breast cancers, where EYA proteins are overexpressed. Additionally, it is involved in the synthesis of Human Uric Acid Transporter 1 inhibitors, which may be used to treat kidney diseases.
Uses
Used in Anticancer Applications:
Benzarone is used as an anticancer agent for its ability to inhibit the EYA protein, which is overexpressed in ovarian and breast cancers. This inhibition helps in controlling tumor growth and progression, making it a valuable compound in the fight against these specific types of cancer.
Used in Pharmaceutical Industry:
Benzarone is used as a key component in the synthesis of Human Uric Acid Transporter 1 inhibitors. These inhibitors are essential for the development of treatments targeting kidney diseases, where the regulation of uric acid transport is crucial for managing the condition and improving patient outcomes.
Used in Research and Development:
As a multifunctional protein inhibitor, Benzarone is also utilized in research and development for its potential applications in understanding the role of EYA proteins in organogenesis and other biological processes. This knowledge can lead to the discovery of new therapeutic approaches and treatments for various diseases and conditions.
Originator
Fragivix,Labaz
Manufacturing Process
The process of preparation of the 2-ethyl-3-(4'-hydroxybenzoyl)benzofurane includes the next steps:
1. To 1 mol of potassium hydroxide in absolute ethanol is added 1 mole of
salicylic aldehyde. The mixture is brought to boiling point in water bath until
the potassium salt formed is dissolved. One mole of coloroacetone is gradually
added and the solution boiled in a reflux condenser for 2 hours. On cooling
the potassium chloride precipitate is separated off by filtration. The residue is
distilled to give 2-acetyl-1-benzofurane, BP: 135°C/15 mm Hg.
2. It was reduced by hydrazine hydrate in an alkaline medium (by process of
Hyuang-Minlon, J.A.C.S., 1946, 68, 2487) to give 2-ethyl-1-benzofurane BP:
211°-212°C.
3. 2-Ethyl-1-benzofurane is condensed with 2-metoxybenzoyl chloride in the
presence of tin tetrachloride (according to the process described by Bisagni,
J.C.S., 1955, 3694). Thus 2-ethyl-3-(4-methoxybenzoyl)-1-benzofyrane is
obtained. BP: 226°C/15 mm Hg.
4. 1 part of 2-ethyl-3-(4-methoxybenzoyl)-1-benzofyrane is mixed with 2
parts of pyridine hydrochloride and heated at an oil bath at 210°C in N2
current for 1 hour. On cooling 10 parts of 0.5 N HCl are added. A water layer
is mixed with 20 parts of 1% NaOH. The alkaline layer is separated, acidified
with diluted HCl. The dropped precipitate (2-ethyl-3-(4'-hydroxybenzoyl)
benzofurane) is recrystallized from acetic acid. MP: 124.3°C.
Therapeutic Function
Antihemorrhagic
World Health Organization (WHO)
Benzarone is given by mouth and applied topically for treatment
of various vascular peripheral disorders.The decision to suspend the marketing
authorization results from several reports of toxic hepatitis, including one fatal
case from within Germany. The product remains registered in Italy and France.
Safety Profile
Poison by
intraperitoneal route. An experimental
teratogen. Other experimental reproductive
effects. A flammable liquid. When heated to
decomposition it emits acrid and irritating
smoke and fumes. See also KETONES.
Check Digit Verification of cas no
The CAS Registry Mumber 1477-19-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,7 and 7 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1477-19:
(6*1)+(5*4)+(4*7)+(3*7)+(2*1)+(1*9)=86
86 % 10 = 6
So 1477-19-6 is a valid CAS Registry Number.
InChI:InChI=1/C17H14O3/c1-2-14-16(13-5-3-4-6-15(13)20-14)17(19)11-7-9-12(18)10-8-11/h3-10,18H,2H2,1H3
1477-19-6Relevant articles and documents
Preparation method of benzbromarone
-
, (2021/03/11)
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of benzbromarone. According to the method disclosed by the invention, polystyrene-loaded aluminum trichloride is used as a catalyst to carry out Friedel-Crafts acylation reaction, so that the catalytic effect is good, and the catalyst can be recycled, in the demethylation reaction process, aluminum trichloride is adopted to replace common pyridine hydrochloride, so that the reaction temperature can be reduced, and the yield can be increased, in the bromination reaction, sodium sulfide and hydrogen peroxide are adopted to replace bromine, so that the technical problems of strong corrosivity of bromine, great harm to human bodies and environmental pollution are solved, and meanwhile, the yield can be further improved.
Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds
Huang, Wenbo,Xu, Jing,Liu, Changhui,Chen, Zhiyan,Gu, Yanlong
, p. 2941 - 2950 (2019/02/26)
2,3-Disubstituted benzofurans were synthesized from acrolein dimer and 1,3-dicarbonyl compounds by using N-bromosuccinimide as an oxidizing agent. The method was used to synthesize two commercial drug molecules, benzbromarone and amiodarone. The proposed mechanism of the reaction involves a N-bromosuccinimide (NBS)-assisted autotandem catalysis with Lewis acid catalyst. To proof the proposed mechanism, an intermediate was isolated successfully, which can be converted to 4,5,6,7-tetrahydrobenzofurans.
Preparation method of 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran
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Paragraph 0030; 0036; 0039; 0042-0044; 0048, (2018/11/04)
The invention discloses a preparation method of 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran. According to the preparation method, at first, 1-(4-methoxyphenyl)-1,3-pentanedione and acrolein dimer are taken as raw materials to carry out reactions in the presence of an acid catalyst and a halogenation reagent to prepare 2-ethyl-3-(4-methoxyphenyl) benzofuran; then 2-ethyl-3-(4-methoxyphenyl) benzofuranis processed in an organic solvent containing an acid catalyst, and after de-methylation reactions, 2-ethyl-3-(4-hydroxylbenzoyl) benzofuran is obtained. The whole process of key preparation technologies and parameters of each reaction step are optimized; and compared with a conventional synthesis method, the provided preparation method has the advantages of good economy, high selectivity, littleenvironmental pollution, and large industrial application value.