63457-22-7

Usage

Chemical class

Phenothiazine derivative

Pharmacological properties

Potential antipsychotic, antiemetic, and antihistaminic effects

Structural features

Contains a 3-chloropropyl group and a carbonitrile group attached to the phenothiazine core

Biological activity

The addition of the 3-chloropropyl and carbonitrile groups may influence the compound's biological activity

Pharmacokinetic properties

The addition of the 3-chloropropyl and carbonitrile groups may influence the compound's pharmacokinetic properties

Research status

Further research may be needed to fully understand the potential applications and effects of 10-(3-chloropropyl)-10H-phenothiazine-2-carbonitrile

Potential applications

As a therapeutic agent for various conditions, such as psychosis, nausea, and allergies, depending on the results of further research

Chemical structure

The phenothiazine core is a tricyclic structure with a sulfur atom and two nitrogen atoms

Synthesis

The compound can be synthesized by attaching the 3-chloropropyl and carbonitrile groups to the phenothiazine core through chemical reactions

InChI:InChI=1/C16H13ClN2S/c17-8-3-9-19-13-4-1-2-5-15(13)20-16-7-6-12(11-18)10-14(16)19/h1-2,4-7,10H,3,8-9H2

Upstream product

• 38642-74-9 10H-phenothiazine-2-carbonitrile 
• 109-70-6 1.3-chlorobromopropane 
• 1778-82-1 phenothiazine-2-carboxamide 
• 92-39-7 2-chlorophenothiazine 
• 6940-76-7 1-iodo-3-chloro-propane 

Relevant academic research and scientific papers

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.

2-Azaadamantane N-oxyl (AZADO)/Cu Catalysis Enables Chemoselective Aerobic Oxidation of Alcohols Containing Electron-Rich Divalent Sulfur Functionalities

The chemoselective oxidation of alcohols containing electron-rich sulfur functionalities (e.g., 1,3-dithianes and sulfides) into their corresponding carbonyl compounds with the sulfur groups can sometimes be a demanding task in modern organic chemistry. A reliable method for this transformation, which features azaadamantane-type nitroxyl radical/copper catalysis using ambient air as the terminal oxidant is reported. The superiority of the developed method was demonstrated by comparing it with various conventional alcohol oxidation methods.

Synthesis and structure-activity relationships of phenothiazine carboxylic acids having pyrimidine-dione as novel histamine H1 antagonists

A series of phenothiazine carboxylic acid derivatives, having 6-amino-pyrimidine-2,4(1H,3H)-dione moiety via a appropriate linker, were synthesized and evaluated for their affinity toward human histamine H1 receptor and Caco-2 cell permeability. Selected compounds were further evaluated for their oral anti-histaminic activity in mice and bioavailability in rats. Finally, promising compounds were examined for their anti-inflammatory potential in mice OVA-induced biphasic cutaneous reaction model. Among the compounds tested, phenothiazineacetic acid compound 27 showed both histamine H1-receptor antagonistic activity and anti-inflammatory activity in vivo model.

Identification of a non peptidic RANTES antagonist

A series of phenothiazines demonstrating inhibition of RANTES binding to THP-1 cell membranes has been identified. The lead compound RP23618 (IC50 = 3 μM) was found to inhibit specific binding of 125I-RANTES, but not 125I-MCP-1 to THP-1 cell membranes and furthermore to antagonise RANTES, but not MCP-1-induced chemotaxis of THP-1 cells.