2632-13-5 Usage
Description
2-Bromo-4'-methoxyacetophenone is an α-haloacetophenone derivative characterized by its off-white to light brown crystalline appearance. It is a potent and covalent inhibitor of protein tyrosine phosphatases, specifically targeting SHP-1 and PTP1B.
Uses
Used in Pharmaceutical Industry:
2-Bromo-4'-methoxyacetophenone is used as a research chemical for the development of protein tyrosine phosphatase inhibitors. Its ability to inhibit these enzymes makes it a valuable tool in studying the role of these enzymes in various biological processes and diseases.
Used in Biochemical Research:
2-Bromo-4'-methoxyacetophenone is used as a cell-permeable, covalent, and potent protein tyrosine phosphatase inhibitor. This property allows researchers to investigate the function and regulation of these phosphatases in cellular signaling pathways, which can provide insights into the development of new therapeutic strategies for various diseases.
Used in Drug Discovery:
2-Bromo-4'-methoxyacetophenone serves as a lead compound in the discovery and optimization of new drugs targeting protein tyrosine phosphatases. Its potent inhibitory activity and cell permeability make it a promising starting point for the design of more effective and selective inhibitors for therapeutic applications.
Preparation
Obtained by reaction of N-bromosuccinimide (NBS) with 4-methoxyacetophenone in the presence of trimethylsilyl trifluoromethanesulfonate (TMS-OTf) in acetonitrile at r.t. for 24 h (87%).
Biological Activity
ki: 128 μmptp inhibitor ii is a protein tyrosine phosphatase (ptp) inhibitor.protein tyrosine phosphatases (ptps) are reported to be involved in the etiology of diabetes mellitus, neural diseases such as alzheimer and parkinson diseases, regulation of allergy and inflammation, or ptps are even regarded to be responsible for the pathogens.
in vitro
in a previous study, it was found that all of the previously reported ptp inhibitors contained a negatively charged, nonhydrolyzable py mimetic as the core structure, such as malonates, aryl carboxylates, phosphonates, or cinnamates. the poor membrane permeability of these inhibitors might compromise their potential development. it was reported that several α-bromoacetophenone derivatives, such as ptp inhibitor ii, could act as fairly potent ptp inhibitors, by covalently alkylating the conserved catalytic cysteine in the ptp active site. since ptp inhibitor ii is neutral, it could readily diffuse into human b cells and inhibit the intracellular ptps. the sar study was performed with the catalytic domain of phosphatase shp-1, and ti was found that ptp inhibitor ii showed time-dependent inactivation of shp-1, consistent with the mechanism. furthermore, the potency of ptp inhibitor ii was described by an equilibrium constant ki, representing the dissociation constant of the noncovalent enzyme–inhibitor complex. ptp inhibitor ii bound with lower affinity than ptp inhibitor i with ki values of 128 μm [1].
references
[1] p. heneberg. use of protein tyrosine phosphatase inhibitors as promising targeted therapeutic drugs. current medicinal chemistry 16(6), 706-733 (2009).
Check Digit Verification of cas no
The CAS Registry Mumber 2632-13-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,6,3 and 2 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 2632-13:
(6*2)+(5*6)+(4*3)+(3*2)+(2*1)+(1*3)=65
65 % 10 = 5
So 2632-13-5 is a valid CAS Registry Number.
InChI:InChI=1/C9H9BrO2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5H,6H2,1H3
2632-13-5Relevant articles and documents
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Kunckell,Scheven
, p. 173 (1898)
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Borowitz,Parnes
, p. 3560 (1967)
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Synthesis of a New Phorbazole and Its Derivatives
Louglin, Wendy A.,Muderawan, I Wayan,Young, David J.
, (2021/11/30)
Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.
Synthesis method of biochanin A
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Paragraph 0012; 0016; 0017; 0018, (2021/08/14)
The invention discloses a synthesis method of biochanin A. The synthesis method comprises the following steps: (1) carrying out condensation reaction on p-methoxyacetophenone and N-bromosuccinimide in the presence of absolute ethyl alcohol to obtain Alpha-bromo-4-methoxyacetophenone; and (2) by taking absolute ethyl alcohol as a reaction solvent, carrying out condensation reaction on 2, 4, 6-trihydroxy benzaldehyde and Alpha-bromo-4-methoxyacetophenone in the presence of a catalyst, evaporating reaction liquid, and separating and purifying a solid product by using column chromatography to obtain the biochanin A. The novel catalyst is adopted for catalysis, the product yield is high, reaction conditions are mild, and raw materials of the catalyst are easy to obtain and low in price. The synthesis method disclosed by the invention is simple in process, low in cost, time-saving, high in yield, low in equipment corrosion degree and suitable for industrial production.