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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Novel hybrid conjugates with dual estrogen receptor α degradation and histone deacetylase inhibitory activities for breast cancer therapy
Zhao, Chenxi,Tang, Chu,Li, Changhao,Ning, Wentao,Hu, Zhiye,Xin, Lilan,Zhou, Hai-Bing,Huang, Jian
supporting information, (2021/05/10)
Hormone therapy targeting estrogen receptors is widely used clinically for the treatment of breast cancer, such as tamoxifen, but most of them are partial agonists, which can cause serious side effects after long-term use. The use of selective estrogen receptor down-regulators (SERDs) may be an effective alternative to breast cancer therapy by directly degrading ERα protein to shut down ERα signaling. However, the solely clinically used SERD fulvestrant, is low orally bioavailable and requires intravenous injection, which severely limits its clinical application. On the other hand, double- or multi-target conjugates, which are able to synergize antitumor activity by different pathways, thus may enhance therapeutic effect in comparison with single targeted therapy. In this study, we designed and synthesized a series of novel dual-functional conjugates targeting both ERα degradation and histone deacetylase inhibiton by combining a privileged SERD skeleton 7-oxabicyclo[2.2.1]heptane sulfonamide (OBHSA) with a histone deacetylase inhibitor side chain. We found that substituents on both the sulfonamide nitrogen and phenyl group of OBHSA unit had significant effect on biological activities. Among them, conjugate 16i with N-methyl and naphthyl groups exhibited potent antiproliferative activity against MCF-7 cells, and excellent ERα degradation activity and HDACs inhibitory ability. A further molecular docking study indicated the interaction patterns of these conjugates with ERα, which may provide guidance to design novel SERDs or PROTAC-like SERDs for breast cancer therapy.
First synthesis of tabamides A–C and their derivatives: In vitro nitric oxide inhibitory activity
Damodar, Kongara,Shin, Sooyong,Jeon, Sung Ho,Lee, Jeong Tae
supporting information, (2021/11/10)
The first synthesis of natural phenolic amides, tabamides A–C (1–3), and their derivatives (4–12) was accomplished using Stobbe condensation and amide coupling reactions as key steps. The in vitro nitric oxide (NO) inhibitory effects of these compounds in LPS-induced RAW-264.7 macrophages were evaluated as an indicator of anti-inflammatory activity. All compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without significant cytotoxicity. Compound 6, a tabamide A derivative (IC50 = 82.6 μM), followed by tabamide A (1, IC50 = 100.7 μM), was the most potent from the series. The present study revealed that tabamide A (1) could be considered as a lead structure to develop NO production-targeted anti-inflammatory agents.