4506-53-0 Usage
Description
4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, which includes a benzene ring fused to a cyclohepta[1,2-b]thiophene ring, with a ketone group at the 4-position. 4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one plays a significant role in the development of new and potent drugs targeting specific receptors.
Uses
Used in Pharmaceutical Industry:
4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one is used as a key intermediate in the synthesis of 10-Deoxo-9,10-dehydro Ketotifen (D231580), which is an impurity of Ketotifen (K315100). 4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one is of interest due to its potential as a new and potent 5-HT2A receptor agonist. The 5-HT2A receptor is a target for various therapeutic applications, including the treatment of psychiatric disorders, such as schizophrenia, and other conditions related to serotonin signaling.
In the synthesis of 10-Deoxo-9,10-dehydro Ketotifen, 4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one serves as a building block that contributes to the formation of the final product. The development of this compound as a potent 5-HT2A receptor agonist highlights its importance in the pharmaceutical industry, where it can be used to create new drugs with improved efficacy and reduced side effects.
Furthermore, the compound's role as an intermediate in the synthesis of other pharmaceutical compounds suggests that it may have additional applications in the development of novel therapeutic agents. As research progresses, it is possible that 4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one will be utilized in the creation of drugs targeting a variety of receptors and pathways, contributing to the advancement of medical treatments for numerous conditions.
Check Digit Verification of cas no
The CAS Registry Mumber 4506-53-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,5,0 and 6 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4506-53:
(6*4)+(5*5)+(4*0)+(3*6)+(2*5)+(1*3)=80
80 % 10 = 0
So 4506-53-0 is a valid CAS Registry Number.
4506-53-0Relevant articles and documents
4H-BENZOCYLOHEPTATHIOPHENES AND 9,10-DIHYDRO DERIVATIVES-SULFONIUM ANALOGUES OF PIZOTIFEN AND KETOTIFEN; CHIRALITY OF KETOTIFEN: SYNTHESIS OF THE 2-BROMO DERIVATIVE OF KETOTIFEN
Polivka, Zdenek,Budesinsky, Milos,Holubek, Jiri,Schneider, Bohdan,Sediva, Zdenek,et al.
, p. 2443 - 2469 (2007/10/02)
Reaction of ketone IX with 4-tetrahydrothiopyranylmagnesium bromide and the following dehydration with thionyl chloride afforded the sulfide III which was transformed to the methiodide II (sulfonium analogue of pizotifen).Similar sequence starting from ketone XXIV and concluded by dehydration of the alcohol XX, cleavage of the enol ether, and by treatment with methyl iodide resulted in the formation of the sulfonium analogue of ketotifen (V).Three modified routes leading to ketotifen (IV) are being described.The chirality of ketotifen was proven by (1)H NMR spectrscopy with the help of,optically active NMR shift reagent.The resolution of racemic ketotifen (IV) was achieved by crystallization of salts with optically active O,O'-diacyltartaric acids and homogenous anantiomers were obtained.The X-ray crystallographic analysis of (+)-IV-O,O'-di(p-toluoyl)-(R)-tartrate led to the three- dimensional structure of the molecule of (+)-ketotifen which enabled to determine its absolute configuration to be (R).One of the products of bromination of the ketone IX, the following methanolysis and dehydrobromonation, identified as XXVII, was transformed by reaction with 1-methyl-4-piperidylmagnesium chloride, by the following acid-catalyzed dehydration, and cleavage of the enol ether to the 2-bromo derivative of ketotifen XXXIV. (R)(+)-Ketotifen (IV) was found to be the more active ketotifen enantiomer but the stereoselectivity of its action is only a partial one.The 2-bromo derivative of ketotifen (XXXIV) is much less active than ketotifen in the line antihistamine activity.
