170655-46-6

Basic information

• Product Name: 2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE
• Synonyms: 2-CHLORO-N-(4-MORPHOLINOPHENYL)ACETAMIDE;2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE;AKOS BBS-00006333;2-chloro-N-(4-morpholinophenyl)acetamide (en)
• CAS NO: 170655-46-6
• Molecular Formula: C₁₂H₁₅ClN₂O₂
• Molecular Weight: 254.71
• Mol File: 170655-46-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 486.1 °C at 760 mmHg
• Flash Point: 247.8 °C
• Appearance: /
• Density: 1.291 g/cm³
• Vapor Pressure: 1.33E-09mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE(170655-46-6)
• EPA Substance Registry System: 2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE(170655-46-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 170655-46-6(Hazardous Substances Data)

Usage

Description

2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE, also known as 2-Chloro-N-(4-morpholin-4-ylphenyl) acetamide, is a chlorinated acetamide derivative with the molecular formula C12H15ClN2O2. It features a morpholine ring and a phenyl group, and is recognized for its wide range of biological activities, such as anti-inflammatory and antitumor properties. This chemical compound is primarily utilized as an intermediate in the synthesis of pharmaceuticals and agrochemicals, and also serves as a building block in the synthesis of various organic compounds for both academic research and industrial applications.

Uses

Used in Pharmaceutical Industry:
2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE is used as an intermediate in the synthesis of various pharmaceuticals for its potential anti-inflammatory and antitumor properties, contributing to the development of new drugs that can address these health concerns.
Used in Agrochemical Industry:
In the agrochemical sector, 2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE is utilized as an intermediate in the production of agrochemicals, potentially enhancing crop protection and management through its biological activities.
Used in Academic Research:
2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE is used as a building block in the synthesis of various organic compounds for academic research, facilitating the exploration of new chemical reactions and the discovery of novel compounds with potential applications.
Used in Industrial Applications:
For industrial applications, 2-CHLORO-N-(4-MORPHOLIN-4-YL-PHENYL)-ACETAMIDE serves as a key component in the synthesis of a range of organic compounds, supporting the innovation and advancement of various chemical processes and products.

InChI:InChI=1/C12H15ClN2O2/c13-9-12(16)14-10-1-3-11(4-2-10)15-5-7-17-8-6-15/h1-4H,5-9H2,(H,14,16)

Upstream product

• 10389-51-2 1-morpholino-4-nitrobenzene 
• 350-46-9 4-Fluoronitrobenzene 
• 586-78-7 para-nitrophenyl bromide 
• 2524-67-6 4-morpholino-4-yl-phenylamine 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 936632-77-8 1-deoxy-1-(6-{4-[(4-morpholin-4-ylphenylcarbamoyl)methoxy]phenylamino}-9H-purin-9-yl)-N-ethyl-2,3-O-(1-methylethylidene)-β-D-ribofuranuronamide 
• 936633-14-6 2-(4-aminophenoxy)-N-(4-morpholinophenyl)acetamide 
• 304675-29-4 N-(4-morpholin-4-ylphenyl)-2-(4-nitrophenoxy)acetamide 

Relevant articles and documents

Design, synthesis and biological evaluation of novel osthole-based derivatives as potential neuroprotective agents

A total of 26 compounds based on osthole skeleton were designed, synthesized. Their cytoprotective abilities of antioxidation, anti-inflammation and Aβ42(Amyloid β-protein 42)-induced neurotoxicity were evaluated by MTT assays. Mechanism of the action of selected compounds were investigated by molecular docking. AlogP, logS and blood–brain barrier (BBB) permeability of all these compounds were simulated by admetSAR. Most of the compounds showed better antioxidative and anti-inflammatory activities compared with osthole, especially OST7 and OST17. The compound OST7 showed relative high activity in neuroprotection against H2O2 (45.7 ± 5.5%), oxygen glucose deprivation (64.6 ± 4.8%) and Aβ42 (61.4 ± 5.2%) at a low concentration of 10 μM. EC50 of selected compounds were measured in both H2O2 and OGD induced cytotoxicity models. Moreover, NO inhibiting ability of OST17(50.4 ± 7.1%) already surpassed the positive drug indomethacin. The structure activity relationship study indicated that introduction of piperazine group, tetrahydropyrrole group and aromatic amine group might be beneficial for enhancement of osthole neuroprotective properties. Molecular docking explained that the reason OST7 exhibited relatively stronger neuroprotection against Aβ because of the greater area of interactions between molecule and target protein. OST7 and OST17 both provided novel methods to investigate osthole as anti-AD drugs.

Synthesis, antiproliferative evaluation, and structure–activity relationships of novel triazole–isoindoline hybrids bearing 3,4,5-trimethoxyphenyl moiety

As an aspect of our ongoing research on developing novel antiproliferative agents, 31 new triazole–isoindoline hybrids bearing 3,4,5-trimethoxyphenyl moiety were synthesized and evaluated for their antiproliferative activity against four cancer cell lines (HepG2, HeLa, PC-3, and HCT116). Some compounds showed excellent potency, and compared to fluorouracil, the most promising compound 6s exhibited 5.8-, 4.3-, and 1.3- fold increase in activities against HeLa, HepG2, and PC-3 cell lines with IC50 values of 9.7, 10.7, and 16.8?μM, respectively. Moreover, structure–activity relationship studies indicated that a much shorter amide linkage and electron-withdrawing groups at phenyl ring of the acetamide fragment contribute to the antitumour activity.

Discovery of novel N -phenylphenoxyacetamide derivatives as EthR inhibitors and ethionamide boosters by combining high-throughput screening and synthesis

In this paper, we describe the screening of a 14640-compound library using a novel whole mycobacteria phenotypic assay to discover inhibitors of EthR, a transcriptional repressor implicated in the innate resistance of Mycobacterium tuberculosis to the second-line antituberculosis drug ethionamide. From this screening a new chemical family of EthR inhibitors bearing an N-phenylphenoxyacetamide motif was identified. The X-ray structure of the most potent compound crystallized with EthR inspired the synthesis of a 960-member focused library. These compounds were tested in vitro using a rapid thermal shift assay on EthR to accelerate the optimization. The best compounds were synthesized on a larger scale and confirmed as potent ethionamide boosters on M. tuberculosis-infected macrophages. Finally, the cocrystallization of the best optimized analogue with EthR revealed an unexpected reorientation of the ligand in the binding pocket.