2765-59-5

Basic information

• Product Name: 2-chloro-10-(3-chloropropyl)-10H-phenothiazine
• Synonyms: 10-(3-Chloropropyl)-2-chloro-10H-phenothiazine;γ-(2-Chlorophenothiazinyl-10)propyl Chloride
• CAS NO: 2765-59-5
• Molecular Formula: C₁₅H₁₃Cl₂NS
• Molecular Weight: 310.2414
• EINECS: 220-438-8
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 2765-59-5.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 454.9 °C at 760 mmHg
• Flash Point: 228.9 °C
• Appearance: /
• Density: 1.325 g/cm³
• Vapor Pressure: 1.84E-08mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 2-chloro-10-(3-chloropropyl)-10H-phenothiazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-10-(3-chloropropyl)-10H-phenothiazine(2765-59-5)
• EPA Substance Registry System: 2-chloro-10-(3-chloropropyl)-10H-phenothiazine(2765-59-5)

Safety Data

• Hazardous Substances Data: 2765-59-5(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

Perphenazine intermediate.

InChI:InChI=1/C15H13Cl2NS/c16-8-3-9-18-12-4-1-2-5-14(12)19-15-7-6-11(17)10-13(15)18/h1-2,4-7,10H,3,8-9H2

Upstream product

• 632-02-0 3-chloropropyl p-toluenesulfonate 
• 92-39-7 2-chlorophenothiazine 
• 109-70-6 1.3-chlorobromopropane 
• 6940-76-7 1-iodo-3-chloro-propane 
• 84-04-8 pipamazine 

Downstream Products

• 58-38-8 prochlorperazine 
• 58-39-9 perphenazine 
• 180388-71-0 N-[3-(2-chloro-phenothiazin-10-yl)-propyl]-phthalimide 
• 2095-17-2 2-chloro-10-(3-aminopropyl)phenothiazine 
• 32418-82-9 2-chloro-10-[3-(octahydro-pyrido[1,2-a]pyrazin-2-yl)-propyl]-10H-phenothiazine 
• 26728-13-2 8-[3-(2-chloro-phenothiazin-10-yl)-propyl]-3-phenyl-1-oxa-3,8-diaza-spiro[4.5]decane-2,4-dione 
• 49614-61-1 3-benzyl-8-[3-(2-chloro-phenothiazin-10-yl)-propyl]-1-oxa-3,8-diaza-spiro[4.5]decane-2,4-dione 
• 14635-36-0 N-{1-[3-(2-chloro-phenothiazin-10-yl)-propyl]-4-phenyl-piperidin-4-ylmethyl}-acetamide 
• 13611-80-8 1-[3-(2-chloro-phenothiazin-10-yl)-propyl]-4-phenyl-piperidin-4-ol 
• 26369-14-2 1-{1-[3-(2-chloro-phenothiazin-10-yl)-propyl]-4-phenyl-piperidin-4-yl}-ethanone 
• 26438-75-5 1-[3-(2-chloro-phenothiazin-10-yl)-propyl]-4-(4-chloro-phenyl)-piperidin-4-ol 
• 64638-16-0 {1-[3-(2-chloro-phenothiazin-10-yl)-propyl]-piperidin-4-yl}-(3,4-dichloro-phenyl)-methanone 
• 50-53-3 2-chloro-N,N-dimethyl-10H-phenothiazine-10-propanamine 
• 57942-72-0 10-[3-(4-adamantan-2-yl-piperazin-1-yl)-propyl]-2-chloro-10H-phenothiazine 

Relevant articles and documents

Charged Analogues of Chlorpromazine as Dopamine Antagonists

Chlorpromazine (1, CPZ) is a potent dopamine antagonist that has been used widely as an antipsychotic agent.Since dopaminergic antagonists, like dopaminergic agonists, exist in solution as the charged and uncharged molecular species, it is not clear which form of the amine is most important for interaction with the dopamine receptor.Previous work from our laboratory has indicated that a variety of permanently charged species could replace the amine/ammonium moiety of dopamine and retain dopamine agonist activity.This paper describes the synthesis and dopamine antagonist activity of both the trimethylammonium iodide (2) and the dimethylsulfonium iodide (3) analogues of chlorpromazine.The permanently uncharged methyl sulfide analogue (4) was also synthesized; however, due to its lack of aqueous solubility, its pharmacological activity could not be evaluated.Binding of both the dimethylsulfonium iodide and the trimethylammonium iodide analogues to D-2 dopamine receptors of rat striatal tissue was observed.The observed relative order of binding was CPZ > CPZ sulfonium analogue > CPZ ammonium analogue.These compounds had a similar order of activity in antagonizing the apomorphine-induced inhibition of potassium-induced release of acetylcholine from mouse striatal slices.

Chemical synthetic platform for chlorpromazine oligomers that were reported as photo-degradation products of chlorpromazine

A synthetic platform for chlorpromazine (CPZ) oligomers, which could be generated via photo-reaction of CPZ, is essential to promote their biological and structural studies. In this paper, the first synthetic platform for CPZ oligomers is described. A photo-irradiation experiment of CPZ to confirm whether the structure of the CPZ dimer generated by the photo-irradiation was identical to that prepared by our synthetic method is also reported.

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.

The phenothiazine compound and its preparation method and application

The invention relates to a phenothiazine compound and a preparation method thereof. The invention further relates the application of the phenothiazine compound in anti-cancer drug preparation and anti-cancer drugs using the compound as the effective component. The phenothiazine compound has the advantages that the compound with broad-spectrum anti-cancer effect is obtained by modifying phenothiazine ternary interlink parent nucleuses, synthesizing method is simple, and high yield is achieved; the phenothiazine compound has certain restraining effect on human breast cancer cells line MCF-7 and human hepatoma cell line Hep-G2, and a new thought is provided to new drugs satisfying clinic requirements.