16189-69-8

Basic information

• Product Name: 2-CHLORO-10-(CHLOROACETYL)-10H-PHENOTHIAZINE
• Synonyms: 2-chloro-1-(2-chloro-10-phenothiazinyl)ethanone;Ethanone, 2-chloro-1-(10H-phenothiazine-10-yl)-
• CAS NO: 16189-69-8
• Molecular Formula: C₁₄H₉Cl₂NOS
• Molecular Weight: 310.2
• Mol File: 16189-69-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 539.9°Cat760mmHg
• Flash Point: 280.3°C
• Appearance: /
• Density: 1.468g/cm³
• Vapor Pressure: 1.01E-11mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: 2-CHLORO-10-(CHLOROACETYL)-10H-PHENOTHIAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-10-(CHLOROACETYL)-10H-PHENOTHIAZINE(16189-69-8)
• EPA Substance Registry System: 2-CHLORO-10-(CHLOROACETYL)-10H-PHENOTHIAZINE(16189-69-8)

Safety Data

• Hazardous Substances Data: 16189-69-8(Hazardous Substances Data)

Usage

General Description

2-Chloro-10-(chloroacetyl)-10H-phenothiazine is a chemical compound with the molecular formula C15H9Cl2NOS. It is a derivative of phenothiazine, a heterocyclic compound that is commonly used in the manufacturing of pharmaceuticals. This specific compound is a phenothiazine derivative that contains two chlorine atoms and a chloroacetyl group. It is used as an intermediate in the synthesis of various pharmaceuticals and organic compounds, and it is also known for its potential biological and pharmacological activities. However, its specific uses and applications are still being researched and investigated.

InChI:InChI=1/C14H9Cl2NOS/c15-8-14(18)17-10-3-1-2-4-12(10)19-13-6-5-9(16)7-11(13)17/h1-7H,8H2

Upstream product

• 101-17-7 3-chlorodiphenylamine 
• 92-39-7 2-chlorophenothiazine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 96761-99-8 2-chloro-10-[(2,4,6-trioxo-5-phenyl-hexahydro-pyrimidin-5-yl)-acetyl]-10H-phenothiazine 
• 904317-69-7 1-(2-chloro-phenothiazin-10-yl)-2-(6,7-dimethoxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl)ethanone 
• 17210-75-2 2-chloro-10-(2'-chloroethyl)-10H-phenothiazine 
• 1423077-61-5 4-trifluoromethoxy-N-(2-(2-chloro-10H-phenothiazin-10-yl)ethyl)benzenesulfonamide 
• 1204531-52-1 1-[2-(2-chloro-10H-phenothiazin-10-yl)-2-oxoethyl]pyrrolidine-2,5-dione 
• 1204531-55-4 1-[2-(2-chloro-10H-phenothiazin-10-yl)-2-oxoethyl]-1H-pyrrole-2,5-dione 
• 86224-76-2 8-Chlorbutaperazin 
• 86224-77-3 8-Chlorbutaperazinoxalat 
• 86209-69-0 <8-3H>Butaperazin 

Relevant articles and documents

An Inhibitor of the Interaction of Survivin with Smac in Mitochondria Promotes Apoptosis

Herein we report the first small molecule that disrupts the survivin-Smac interaction taking place in mitochondria. The inhibitor, PZ-6-QN, was identified by initially screening a phenothiazine library using a fluorescence anisotropy assay and then conducting a structure–activity relationship study. Mutagenesis and molecular docking studies suggest that PZ-6-QN binds to survivin similarly to the known Smac peptide, AVPI. The results of the effort also show that PZ-6-QN exhibits good anticancer activity against various cancer cells. Moreover, cell-based mechanistic studies provide evidence for the proposal that PZ-6-QN enters mitochondria to inhibit the survivin-Smac interaction and promotes release of Smac and cytochrome c from mitochondria into the cytosol, a process that induces apoptosis in cancer cells. Overall, the present study suggests that PZ-6-QN can serve as a novel chemical probe for study of processes associated with the mitochondrial survivin-Smac interaction and it will aid the discovery of novel anticancer agents.

Phenothiazines nitric oxide donor, its preparation and use

The invention discloses a kind of phenothiazine-containing nitric oxide donor compounds with the structure of a formula I. In the formula I, n is equal to 0, 1 or 2, R1 is hydrogen, halogens, C1-C4 branched or linear alkyl, or halogenated C1-C4 branched or linear alkyl, and R2 is hydrogen or C1-C4 branched or linear alkyl. The invention also discloses a preparation method of the compounds, and discloses a pharmaceutical composition taking the compounds as an active composition, and application of the compounds as anti-tumor medicines, especially to prepare medicines for treating breast cancer, lung cancer and stomach cancer.

Reengineered tricyclic anti-cancer agents

The phenothiazine and dibenzazepine tricyclics are potent neurotropic drugs with a documented but underutilized anti-cancer side effect. Reengineering these agents (TFP, CPZ, CIP) by replacing the basic amine with a neutral polar functional group (e.g., RTC-1, RTC-2) abrogated their CNS effects as demonstrated by in vitro pharmacological assays and in vivo behavioral models. Further optimization generated several phenothiazines and dibenzazepines with improved anti-cancer potency, exemplified by RTC-5. This new lead demonstrated efficacy against a xenograft model of an EGFR driven cancer without the neurotropic effects exhibited by the parent molecules. Its effects were attributed to concomitant negative regulation of PI3K-AKT and RAS-ERK signaling.