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
- Molecular Weight:
- 241.31
- MDL Number:
- MFCD00005017
- MOL File:
- 6631-94-3.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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) |
| FDA UNII | 8DEE7H3XAB |
| UNSPSC Code | 41121801 |
| NACRES | NA.77 |
2-Acetylphenothiazine price More Price(68)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 175226 | 2-Acetylphenothiazine 95% | 6631-94-3 | 25g | $206 | 2026-04-30 | Buy |
| Sigma-Aldrich | 175226 | 2-Acetylphenothiazine 95% | 6631-94-3 | 100g | $730 | 2026-04-30 | Buy |
| TCI Chemical | A2815 | 2-Acetylphenothiazine >98.0%(GC) | 6631-94-3 | 5g | $199 | 2026-04-30 | Buy |
| TCI Chemical | A2815 | 2-Acetylphenothiazine >98.0%(GC) | 6631-94-3 | 25g | $577 | 2026-04-30 | Buy |
| Cayman Chemical | 19056 | 2-Acetylphenothiazine ≥98% | 6631-94-3 | 10g | $36 | 2026-04-30 | Buy |
2-Acetylphenothiazine Chemical Properties,Uses,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
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Jiaxing Carry Chemical Co.,Ltd. | 18258318278 | info@carrybiotech.com | China | 38 | 55 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| INTATRADE GmbH | +49 3493/605464 | sales@intatrade.de | Germany | 3563 | 66 |
| TCI (Shanghai) Development Co., Ltd. | 021-67121386 | Sales-CN@TCIchemicals.com | China | 24512 | 81 |
| Beijing HwrkChemical Technology Co., Ltd | 89508211 18501085097 | sales.bj@hwrkchemical.com | China | 9407 | 55 |
| Energy Chemical | 400-0056266 | sales8178@energy-chemical.com | China | 44850 | 61 |
| Nanjing Chemlin Chemical Co., Ltd | 025-83697070 13770331960 | info@chemlin.com.cn | China | 16305 | 64 |
| Shanghai Hanhong Scientific Co.,Ltd. | 021-54306202 13764082696 | info@hanhongsci.com | China | 42917 | 64 |
| Chemsky（shanghai）International Co.,Ltd. | 021-50135380 | shchemsky@sina.com | China | 32273 | 50 |
| Syntechem Co.,Ltd | info@syntechem.com | China | 12973 | 57 |
View Lastest Price from 2-Acetylphenothiazine manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2020-01-09 | 2-Acetylphenothiazine
6631-94-3
|
$1.00 | 1ASSAYS | 85.0-99.8% | 20tons | Career Henan Chemical Co |
-
- 2-Acetylphenothiazine
6631-94-3
- $1.00
- 85.0-99.8%
- Career Henan Chemical Co
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