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

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

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

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

Downstream Products

• 304675-29-4 N-(4-morpholin-4-ylphenyl)-2-(4-nitrophenoxy)acetamide 
• 936633-14-6 2-(4-aminophenoxy)-N-(4-morpholinophenyl)acetamide 
• 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 

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.

Discovery and Development of N-[4-(1-Cyclobutylpiperidin-4-yloxy)phenyl]-2-(morpholin-4-yl)acetamide Dihydrochloride (SUVN-G3031): A Novel, Potent, Selective, and Orally Active Histamine H3 Receptor Inverse Agonist with Robust Wake-Promoting Activity

A series of chemical optimizations guided by in vitro affinity at a histamine H3 receptor (H3R), physicochemical properties, and pharmacokinetics in rats resulted in identification of N-[4-(1-cyclobutyl-piperidin-4-yloxy)phenyl]-2-(morpholin-4-yl)acetamide dihydrochloride (17v, SUVN-G3031) as a clinical candidate. Compound 17v is a potent (hH3R Ki = 8.73 nM) inverse agonist at H3R with selectivity over other 70 targets, Compound 17v has adequate oral exposures and favorable elimination half-lives both in rats and dogs. It demonstrated high receptor occupancy and marked wake-promoting effects with decreased rapid-eye-movement sleep in orexin-B saporin lesioned rats supporting its potential therapeutic utility in treating human sleep disorders. It had no effect on the locomotor activity at doses several fold higher than its efficacious dose. It is devoid of hERG and phospholipidosis issues. Phase-1 evaluation for safety, tolerability, and pharmacokinetics, and long-term safety studies in animals have been successfully completed without any concern for further development.

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.

Synthesis and biological evaluation of some novel dithiocarbamate derivatives

18 novel dithiocarbamate derivatives were synthesized in order to investigate their inhibitory potency on acetylcholinesterase enzyme and antimicrobial activity. Structures of the synthesized compounds were elucidated by spectral data and elemental analyses. The synthesized compounds showed low enzyme inhibitory activity. However, they displayed good antimicrobial activity profile. Antibacterial activity of compounds 4a, 4e, and 4p (MIC = 25 g/mL) was equal to that of chloramphenicol against Klebsiella pneumoniae (ATCC 700603) and Escherichia coli (ATCC 35218). Most of the compounds exhibited notable antifungal activity against Candida albicans (ATCC 10231), Candida glabrata (ATCC 90030), Candida krusei (ATCC 6258), and Candida parapsilosis (ATCC 7330). Moreover, compound 4a, which carries piperidin-1-yl supstituent and dimethylthiocarbamoyl side chain as variable group, showed twofold better anticandidal effect against all Candida species than reference drug ketoconazole.

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.

N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor

A new series of N6-[(hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro)-5′-N-ethylcarboxamido-adenosines (24-43) has been synthesised and tested in binding assays at hA1, hA2A and hA3 adenosine receptors, and in a functional assay at the hA2B subtype. The examined compounds displayed high potency in activating A2B receptors with good selectivity versus A2A subtypes. The introduction of an unsubstituted 4-[(phenylcarbamoyl)-methoxy]-phenyl chain at the N6 position of 5′-N-ethylcarboxamido-adenosine led us to the recognition of compound 24 as a full agonist displaying the highest efficacy of the series (EC50 hA2B = 7.3 nM). These compounds represent the first report about adenosine-related structures capable of activating hA2B subtype in the low nanomolar range.