2-Acetylphenothiazine
- Product Name
- 2-Acetylphenothiazine
- CAS No.
- 6631-94-3
- Chemical Name
- 2-Acetylphenothiazine
- Synonyms
- 2-APT;ML 171;2-Acetylphenothiazin;2-ACETYLPHENOTHIAZINE;NOX1 Inhibitor, ML171;LABOTEST-BB LT00012652;2-Acetyl-10H-phenothiazine;2-Acetylphenothiazine(ML171);methyl phenothiazin-2-yl ketone;Ethanone, 1-(10H-phenothiazin-2-yl)-
- CBNumber
- CB7368424
- Molecular Formula
- C14H11NOS
- Formula Weight
- 241.31
- MOL File
- 6631-94-3.mol
2-Acetylphenothiazine Property
- Melting point:
- 180-185 °C (lit.)
- Boiling point:
- 455.7±34.0 °C(Predicted)
- Density
- 1.249±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- pka
- -2.45±0.20(Predicted)
- form
- Dark yellow-orange powder
- color
- Yellow to Dark Orange
- λmax
- 244nm(MeOH)(lit.)
- InChI
- InChI=1S/C14H11NOS/c1-9(16)10-6-7-14-12(8-10)15-11-4-2-3-5-13(11)17-14/h2-8,15H,1H3
- InChIKey
- JWGBOHJGWOPYCL-UHFFFAOYSA-N
- SMILES
- C(=O)(C1=CC=C2C(=C1)NC1=C(C=CC=C1)S2)C
- CAS DataBase Reference
- 6631-94-3(CAS DataBase Reference)
N-Bromosuccinimide Price
- Product number
- 175226
- Product name
- 2-Acetylphenothiazine
- Purity
- 95%
- Packaging
- 25g
- Price
- $135.1
- Updated
- 2025/07/31
- Product number
- 175226
- Product name
- 2-Acetylphenothiazine
- Purity
- 95%
- Packaging
- 100g
- Price
- $480.2
- Updated
- 2025/07/31
- Product number
- A2815
- Product name
- 2-Acetylphenothiazine
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $197
- Updated
- 2025/07/31
- Product number
- A2815
- Product name
- 2-Acetylphenothiazine
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $572
- Updated
- 2025/07/31
- Product number
- 19056
- Product name
- 2-Acetylphenothiazine
- Purity
- ≥98%
- Packaging
- 10g
- Price
- $32
- Updated
- 2024/03/01
2-Acetylphenothiazine Chemical Properties,Usage,Production
Description
2-Acetylphenothiazine (2-APT) is a selective, cell-active inhibitor of NADPH oxidase 1 (NOX1) that blocks the generation of reactive oxygen species (ROS) in HT-29 cells with an IC50 value of 0.129 μM. It does not affect xanthine oxidase-dependent or mitochondrial ROS generation. 2-APT prevents ROS-dependent formation of ECM-degrading invadopodia in colon cancer cells. It also abolishes collagen-induced superoxide production by platelets (IC50 = 306 nM), preventing platelet aggregation and thrombus formation. 2-APT protects beta cells from cytokine-induced apoptosis by inhibiting NOX1. 2-APT can also activate the human transient receptor potential ankyrin 1 (TRPA1) nociceptor at 1-30 μM.
Chemical Properties
Yellow white or green crystalline powder
Uses
2-Acetylphenothiazine is a potent and selective NADPH oxidase 1 (NOX1) inhibitor that blocks NOX1-dependent ROS generation. 2-Acetylphenothiazine has been shown to inhibit SrcYF-induced invadopodia formation in human DLD1 colon cancer cells.
Uses
2-Acetylphenothiazine was used as a NADPH oxidase (NOX) inhibitor in human platelet functional responses and intracellular signaling pathways. It was also used in the synthesis of 2-phenothiazin-2′-yl-cinchoninic acid derivatives.
Definition
ChEBI: 1-(10H-phenothiazin-2-yl)ethanone is a member of phenothiazines.
Synthesis
23699-65-2
6631-94-3
The general procedure for the synthesis of 2-acetylphenothiazine from 1-(3-phenylaminophenyl)-acetophenone was as follows: first, aniline and m-acetylphenol were added to the reaction vessel in a mass ratio of 1.2:1 and heated until dissolved. Subsequently, trifluoromethanesulfonic acid (the amount added was 0.025 times the mass of m-acetylphenol) was added and the dehydration reaction was carried out at 190 °C. The water generated was separated during the reaction. The reaction was terminated after 6 hours. Excess aniline was removed by distillation under reduced pressure to give a dark red solid, 3-acetyl diphenylamine (Compound A). Next, Compound A was added to a reaction vessel with sulfur (molar ratio of Compound A to sulfur is 1:2.3) and 250 mL of acetone (total mass of sulfur and monomers is 1 mole) and heated to dissolve to form a clear liquid. Then, iodine was added (the amount added was 0.0125 times the mass of compound A), and the reaction was stirred and refluxed at 170 °C. After 25 min, the reaction was essentially complete, the stirring was stopped, and the reaction was gradually cooled down to 120 °C, when a yellow and a black delamination was visible. The upper layer of yellow liquid was carefully decanted and a yellow solid was precipitated after cooling at room temperature. The crude product was recrystallized by ethanol-water mixed solvent to give a light yellow solid, i.e., the target product 2-acetylphenothiazine. The total yield in this embodiment was 90.5% and the HPLC purity was 99.7%.
IC 50
NOX1
References
[1] Patent: CN105461655, 2016, A. Location in patent: Paragraph 0033
[2] Patent: CN105481793, 2016, A. Location in patent: Paragraph 0038; 0041
2-Acetylphenothiazine Preparation Products And Raw materials
Raw materials
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View Lastest Price from 2-Acetylphenothiazine manufacturers
- Product
- 2-Acetylphenothiazine 6631-94-3
- Price
- US $1.00/ASSAYS
- Min. Order
- 1ASSAYS
- Purity
- 85.0-99.8%
- Supply Ability
- 20tons
- Release date
- 2020-01-08