786-50-5

Basic information

• Product Name: 10-(chloroacetyl)-10H-phenothiazine
• Synonyms: 2-Chloro-1-phenothiazin-10-yl-ethanone;2-chloro-1-(10-phenothiazinyl)ethanone;EINECS 212-326-2;NCIOpen2_003762;NSC239984;NSC71676;SBB009876;ZINC00507778
• CAS NO: 786-50-5
• Molecular Formula: C₁₄H₁₀ClNOS
• Molecular Weight: 275.76
• EINECS: 212-326-2
• Mol File: 786-50-5.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 498.6°Cat760mmHg
• Flash Point: 255.3°C
• Appearance: /
• Density: 1.383g/cm³
• Vapor Pressure: 4.49E-10mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 10-(chloroacetyl)-10H-phenothiazine(CAS DataBase Reference)
• NIST Chemistry Reference: 10-(chloroacetyl)-10H-phenothiazine(786-50-5)
• EPA Substance Registry System: 10-(chloroacetyl)-10H-phenothiazine(786-50-5)

Safety Data

• Hazardous Substances Data: 786-50-5(Hazardous Substances Data)

Usage

Description

10-(Chloroacetyl)-10H-phenothiazine is a chemical compound derived from phenothiazine, a heterocyclic structure with a sulfur and nitrogen atom. It features a chloroacetyl group attached at the 10th position, which provides unique chemical properties and reactivity. This modification allows for the synthesis of various phenothiazine-based derivatives with potential applications in different fields.

Uses

Used in Pharmaceutical Synthesis:
10-(Chloroacetyl)-10H-phenothiazine is used as a key intermediate in the synthesis of phenothiazine-based pharmaceutical compounds. Its chloroacetyl group can be further modified or used to attach other functional groups, leading to the development of new drugs with specific therapeutic properties.
Used in Anticancer Drug Development:
10-(Chloroacetyl)-10H-phenothiazine is used as a precursor for the synthesis of phenstatin analogues, which exhibit anti-proliferative activity. These analogues have the potential to inhibit the growth of cancer cells by interacting with tubulin, a protein that plays a crucial role in cell division. This interaction can lead to the disruption of the cell cycle and the eventual death of cancerous cells.
Used in Medicinal Chemistry Research:
10-(Chloroacetyl)-10H-phenothiazine serves as a valuable compound in medicinal chemistry research, where it can be used to explore the structure-activity relationships of phenothiazine derivatives. By studying the effects of various modifications to the chloroacetyl group and other parts of the molecule, researchers can gain insights into the design of more effective and targeted therapeutic agents.

InChI:InChI=1/C14H10ClNOS/c15-9-14(17)16-10-5-1-3-7-12(10)18-13-8-4-2-6-11(13)16/h1-8H,9H2

Upstream product

• 92-84-2 10H-phenothiazine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 84409-81-4 2-Amino-3-phenyl-propionic acid N'-(2-oxo-2-phenothiazin-10-yl-ethyl)-hydrazide 
• 84409-84-7 4-Amino-4-[N'-(2-oxo-2-phenothiazin-10-yl-ethyl)-hydrazinocarbonyl]-butyramide 
• 84409-82-5 2-Amino-3-(4-hydroxy-phenyl)-propionic acid N'-(2-oxo-2-phenothiazin-10-yl-ethyl)-hydrazide 
• 80491-64-1 10-(p-Acetylphenoxyacetyl)phenothiazine 
• 80838-33-1 N-[2-(2-Oxo-2-phenothiazin-10-yl-ethoxy)-phenyl]-acetamide 
• 80838-38-6 2-(2-Methoxy-phenoxy)-1-phenothiazin-10-yl-ethanone 
• 80491-62-9 10-(o-Acetylphenoxyacetyl)phenothiazine 
• 119003-43-9 2-<(diisopropoxyphosphinothioyl)imino>-3-phenyl-4-thiazolidinone 
• 80838-32-0 10-<2-(2,3-dihydroxypropyloxy)>phenylaminoacetylphenothiazine 
• 80838-40-0 N-[3-Methyl-4-(2-oxo-2-phenothiazin-10-yl-ethoxy)-phenyl]-acetamide 
• 80838-35-3 N-[2-Methyl-4-(2-oxo-2-phenothiazin-10-yl-ethoxy)-phenyl]-acetamide 
• 80491-63-0 10-(m-Acetylphenoxyacetyl)phenothiazine 
• 92-84-2 10H-phenothiazine 
• 420-04-2 CYANAMID 

Relevant articles and documents

Dithiocarbamate substituted phenothiazine derivatives: In silico experiments, synthesis, and biological evaluation

Objective: The present study was designed to study the anticancer activity of a series of novel analogs of phenothiazine with dithiocarbamate as a side chain. Methods: A novel series of derivatives containing dithiocarbamate as a side chain at the tenth position of phenothiazine nucleus were synthesized, characterized by spectral analysis, and evaluated for their antimitotic and antioxidant activity using germinated Bengal gram seeds and 2,2-diphenyl-1-picrylhydrazyl (DPPH) method, respectively. A quantitative estimate of drug-likeness was also performed, which calculated the molecular properties and screened the molecules based on drug-likeness rules. Further, molecular docking study was performed for finding the binding affinity with tubulin protein to rationalize their anticancer activity. Results: The results revealed that the antioxidant activity of compounds 3e, 3g, 3i, 3j and standard Ascorbic acid were 10 mmol, 14 mmol, 16 mmol, 16 mmol and 35 mmol, respectively. Further compounds 3e, 3g, 3h and 3i have shown promising antimitotic activity. Compound 3i (-9 K. Cal/mol) showed the highest binding energies towards tubulin protein when compared to standard drug colchicine (-8.6 K. Cal/mol). Among all, compound 3i showed promising antimitotic and antioxidant activity, which correlated with insilico docking studies. Conclusion: Dithiocarbamate substituted phenothiazine derivatives proved to be encouraging leads as tubulin inhibitors.

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.

Inhibitory effect of phenothiazine- and phenoxazine-derived chloroacetamides on Leishmania major growth and Trypanosoma brucei trypanothione reductase

A number of phenothiazine-, phenoxazine- and related tricyclics-derived chloroacetamides were synthesized and evaluated in vitro for antiprotozoal activities against Leishmania major (L. major) promastigotes. Several analogs were remarkably potent inhibitors, with antileishmanial activities being comparable or superior to those of the reference antiprotozoal drugs. Furthermore, we explored the structure-activity relationships of N-10 haloacetamides that influence the potency of such analogs toward inhibition of L. major promastigote growth in vitro. With respect to the mechanism of action, selected compounds were evaluated for time-dependent inactivation of Trypanosoma brucei trypanothione reductase. Our results are indicative of a covalent interaction which could account for potent antiprotozoal activities.