2153-08-4

Basic information

• Product Name: 2-Chloro-p-acetophenetidide
• Synonyms: 2-Chloro-p-acetophenetidide;2-chloro-N-(4-ethoxyphenyl)ethanamide;2-chloro-N-(4-ethoxyphenyl)acetamide(SALTDATA: FREE);Acetamide, 2-chloro-N-(4-ethoxyphenyl)- (9CI);N-(Chloroacetyl)-p-phenetidide;p-Acetophenetidide, 2-chloro-;p-Phenetidine, N-chloroacetyl-;WLN: G1VMR DO2
• CAS NO: 2153-08-4
• Molecular Formula: C₁₀H₁₂ClNO₂
• Molecular Weight: 213.67
• Mol File: 2153-08-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 387.1 °C at 760 mmHg
• Flash Point: 187.9 °C
• Appearance: /
• Density: 1.225 g/cm³
• Vapor Pressure: 3.38E-06mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: 2-Chloro-p-acetophenetidide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-p-acetophenetidide(2153-08-4)
• EPA Substance Registry System: 2-Chloro-p-acetophenetidide(2153-08-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 2153-08-4(Hazardous Substances Data)

Usage

General Description

2-Chloro-p-acetophenetidide, also known as chloroacetanilide, is a chemical compound with the molecular formula C8H8ClNO2. It is a white crystalline solid with a slightly medicinal odor that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 2-Chloro-p-acetophenetidide has been found to have anti-inflammatory and analgesic properties, making it a potential candidate for the development of new drugs. It is also used in the production of dyes and pigments. However, this compound is toxic and should be handled with caution, as it may cause irritation to the skin, eyes, and respiratory tract. Overall, 2-Chloro-p-acetophenetidide is a versatile chemical with various industrial and medicinal applications.

InChI:InChI=1/C10H12ClNO2/c1-2-14-9-5-3-8(4-6-9)12-10(13)7-11/h3-6H,2,7H2,1H3,(H,12,13)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 156-43-4 4-Ethoxyaniline 
• 79-07-2 Chloroacetamide 

Downstream Products

• 58479-94-0 N-Piperidinoacetyl-4-ethoxyanilin 
• 103-97-9 Phenocoll 
• 17823-26-6 2-(4-ethoxy-anilino)-thiazol-4-one 
• 99841-71-1 (4-ethoxy-phenylcarbamimidoylmercapto)-acetic acid 
• 65447-01-0 N,N-diethyl-glycine p-phenetidide 
• 40403-45-0 N,N'-bis-(4-ethoxy-phenyl)-2-chloro-acetamidine 
• 380195-34-6 chloro-acetic acid-(4-ethoxy-2-nitro-anilide) 
• 861036-54-6 (6-ethoxy-3-chloro-2-chloromethyl-[4]quinolyl)-(4-ethoxy-phenyl)-amine 
• 21303-71-9 1,4-bis(4-ethoxyphenyl)piperazine-2,5-dione 

Relevant articles and documents

Design, synthesis, and biological evaluation of novel FXR agonists based on auraptene

Farnesoid X receptor (FXR) has been considered as an attractive target for metabolic disorder and liver injury, while many current FXR agonists suffer from undesirable side effects, such as pruritus. Therefore, it is urgent to develop new structure types different from current FXR agonists. In this study, a series of structural optimizations were introduced to displace the unstable coumarin and geraniol scaffolds of auraptene (AUR), a novel and safe FXR agonist. All of these efforts led to the identification of compound 14, a potent FXR agonist with nearly fourfold higher activity than AUR. Molecular modeling study suggested that compound 14 fitted well with binding pocket, and formed the key ionic bond with His291 and Arg328. In acetaminophen-induced acute liver injury model, compound 14 exerts better therapeutic effect than that of AUR, which highlighting its pharmacological potential in the treatment of drug-induced liver injury.

Cink4T, a quinazolinone-based dual inhibitor of Cdk4 and tubulin polymerization, identified via ligand-based virtual screening, for efficient anticancer therapy

Inhibition of cyclin dependent kinase 4 (Cdk4) prevents cancer cells from entering the early G0/G1 phase of the cell division cycle whereas inhibiting tubulin polymerization blocks cancer cells’ ability to undergo mitosis (M) late in the cell cycle. We had reported earlier that two non-planar and relatively non-toxic fascaplysin derivatives, an indole and a tryptoline, inhibit Cdk4 with IC50 values of 6.2 and 10 μM, respectively. Serendipitously, we had also found that they inhibited tubulin polymerization. The molecules were efficacious in mouse tumor models. We have now identified Cink4T in a 59-compound quinazolinone library, designed on the basis of ligand-based virtual screening, as a compound that inhibits Cdk4 and tubulin. Its IC50 value for Cdk4 inhibition is 0.47 μM and >50 μM for inhibition of Cdk1, Cdk2, Cdk6, Cdk9. Cink4T inhibits tubulin polymerization with an IC50 of 0.6 μM. Molecular modelling studies on Cink4T with Cdk4 and tubulin crystal structures lend support to these observations. Cancer cell cycle analyses confirm that Cink4T blocks cells at both G0/G1 and M phases as it should if it were to inhibit both Cdk4 and tubulin polymerization. Our results show, for the very first time, that virtual screening can be used to design novel inhibitors that can potently block two crucial phases of the cell division cycle.

Synthesis, in?vitro evaluation and molecular docking studies of novel triazine-triazole derivatives as potential α-glucosidase inhibitors

A novel series of triazine-triazole derivatives 7a–7m were synthesized, characterized by1H NMR and evaluated for their α-glucosidase inhibitory activity. All the synthesized compounds displayed potent α-glucosidase inhibitory activity with IC50range of 11.63?±?0.15 to 37.44?±?0.35?μM, when compared to the standard drug acarbose (IC50?=?817.38?±?6.27?μM). Among the series, compound 7i (IC50?=?11.63?±?0.15?μM) bearing 2,5-dichloro substitution at phenyl ring, represented the most potent α-glucosidase inhibitory activity. Molecular docking studies of the most active compounds with the homology modelled α-glucosidase were also performed to explore the possible inhibitory mechanism. Our studies shown that these triazine-triazole derivatives are a new class of α-glucosidase inhibitors.