1477-19-6 Usage
Chemical Properties
Pale Yellow Solid
Originator
Fragivix,Labaz
Uses
Benzarone is an EYA (Eyes Absents), multifunctional protein involved in organogenesis, inhibitor which makes it a potent anticancer agent. EYA’s are over expressed in ovarian and breast cancers. As well it is involved in the synthesis of Human Uric Acid Transporter 1 inhibitors which may be used to treat kidney diseases.
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.
Brand name
Benzarin;Fragivix (r) forte;Vasco.
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.
Industrial production method of benzarone
-
Paragraph 0016-0030, (2018/09/12)
The invention relates to an industrial production method of benzarone. The method comprises the following steps: (1) 2-ethylbenzofuran, 4-methoxybenzoyl chloride and an inert solvent are added to a reactor and subjected to a reaction at 15-30 DEG C for 0.5-1 h, Lewis acid is added in batches, a thermal insulated reaction is performed for 3-4 h, then quenching, acidification, water washing, distillation, crystallization and filtering are performed, and a benzarone intermediate is obtained; (2) the benzarone intermediate, Lewis acid and the inert solvent are added to another reactor and subjected to a reaction at 15-30 DEG C for 0.5-1 h, the temperature is increased to 100 DEG C or lower, a thermal insulated reaction is performed for 2-3 h, the same postprocessing is performed, and benzaroneis obtained. Friedel-Crafts acylation is adopted, reaction conditions are relatively mild, high temperature and high energy consumption are avoided, so that the problems of high temperature and low yield in production in the prior art are solved, and the method has good application prospect.
