2-Bromo-4'-hydroxyacetophenone
Synonym(s):p-Hydroxyphenacyl bromide;2-Bromo-1-(4-hydroxyphenyl)ethanone;Protein Tyrosine Phosphatase Inhibitor I, α-Bromo-4-hydroxyacetophenone, 4-Hydroxyphenacyl Br, SHP1 Inhibitor II;PTP Inhibitor I - CAS 2491-38-5 - Calbiochem
- CAS NO.:2491-38-5
- Empirical Formula: C8H7BrO2
- Molecular Weight: 215.04
- MDL number: MFCD00072424
- EINECS: 219-655-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-20 11:41:24
What is 2-Bromo-4'-hydroxyacetophenone?
Description
PTP Inhibitor I is a cell-permeable, protein tyrosine phosphatase (PTP) inhibitor that covalently blocks the catalytic domain of the Src homology region 2 domain-containing phosphatase (SHP-1(ΔSH2)) with a Ki value of 43 μM and PTP1B with a Ki value of 42 μM. SHP-1 and PTP1B both have known roles in regulating insulin signaling as well as myeloid and lymphoid cell differentiation, making inhibitors of these phosphatases of interest in diabetes, cancer, allergy, and inflammation research.
Chemical properties
Pale Beige Solid
The Uses of 2-Bromo-4'-hydroxyacetophenone
A covalent inhibitor of protein tyrosine phosphatases (PTPs)
What are the applications of Application
PTP Inhibitor I is a potent covalent inhibitor of protein tyrosine phosphatases SHP-1 and PTPIB
Preparation
Also obtained by reaction of pyridinium hydrobromide perbromide with 4-hydroxyacetophenone in THF at r.t. for 3 h.
in vitro
in previous study, the corresponding values of ptp inhibitor i against ptp1b were determined to be ki of 42 μm, kinact of 0.57 min-1, and kinact/ki of 1.4*104 m-1 min-1, respectively. this study also showed that α-bromoacetophenone such as ptp inhibitor i could provide an effective, neutral py mimetic inhibitor of ptps. while perturbation of the electronic properties of the phenyl ring did not significantly improve its potency against ptps, attachment of a proper peptidyl moiety to the para position could improve both the potency and the selectivity substantially. in addition, since the covalent ptp inhibitor complex could be cleaved to regenerate the ptp activity photolytically, ptp inhibitor i might provide a novel class of photolytic switch for controlling cellular signaling processes [1].
References
[1] arabaci g, yi t, fu h, porter me, beebe kd, pei d. alpha-bromoacetophenone derivatives as neutral protein tyrosine phosphatase inhibitors: structure-activity relationship. bioorg med chem lett. 2002 nov 4;12(21):3047-50.
Properties of 2-Bromo-4'-hydroxyacetophenone
Melting point: | 123-126°C |
Boiling point: | 338.7±17.0 °C(Predicted) |
Density | 1.622±0.06 g/cm3(Predicted) |
storage temp. | Inert atmosphere,2-8°C |
solubility | Chloroform (Slightly), Methanol (Slightly) |
form | White powder |
pka | 7.69±0.15(Predicted) |
color | White to Light Beige |
Sensitive | Lachrymatory |
BRN | 1865388 |
Stability: | Hygroscopic |
CAS DataBase Reference | 2491-38-5(CAS DataBase Reference) |
EPA Substance Registry System | 2-Bromo-4-hydroxyacetophenone (2491-38-5) |
Safety information for 2-Bromo-4'-hydroxyacetophenone
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for 2-Bromo-4'-hydroxyacetophenone
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