5453-65-6

Basic information

• Product Name: 2-Chloro-N-naphthalen-2-yl-acetamide
• Synonyms: 2-Chloro-N-naphthalen-2-yl-acetamide;2-chloro-N-naphthalen-2-yl-ethanamide;NSC18827;STK117605;ZINC01561899
• CAS NO: 5453-65-6
• Molecular Formula: C₁₂H₁₀ClNO
• Molecular Weight: 219.67
• Mol File: 5453-65-6.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 443.7 °C at 760 mmHg
• Flash Point: 222.1 °C
• Appearance: /
• Density: 1.307 g/cm³
• Vapor Pressure: 4.54E-08mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 2-Chloro-N-naphthalen-2-yl-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N-naphthalen-2-yl-acetamide(5453-65-6)
• EPA Substance Registry System: 2-Chloro-N-naphthalen-2-yl-acetamide(5453-65-6)

Safety Data

• Hazardous Substances Data: 5453-65-6(Hazardous Substances Data)

Usage

General Description

2-Chloro-N-naphthalen-2-yl-acetamide, also known as 2-chloro-N-(naphthalen-2-yl)acetamide, is a chemical compound with the molecular formula C12H10ClNO. It is a chlorinated acetamide derivative of naphthalene, and is used in the synthesis of various pharmaceuticals and agrochemicals. 2-Chloro-N-naphthalen-2-yl-acetamide is primarily used as an intermediate in the production of other chemicals and does not have any specific commercial applications on its own. It is important to handle this chemical with care as it may be harmful if ingested, inhaled, or comes into contact with skin or eyes. Proper safety precautions and handling procedures should be followed when working with 2-Chloro-N-naphthalen-2-yl-acetamide to avoid any potential health risks.

InChI:InChI=1/C12H10ClNO/c13-8-12(15)14-11-6-5-9-3-1-2-4-10(9)7-11/h1-7H,8H2,(H,14,15)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 91-59-8 naphthalen-2-ylamine 

Downstream Products

• 63238-04-0 4-amino-2-(methylthio)-N-(naphthalen-2-yl)thiazole-5-carboxamide 
• 84327-89-9 2-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-N-naphthalen-2-yl-acetamide 
• 17172-55-3 2-(4-formylphenoxy)-N-(naphthalen-2-yl)acetamide 
• 374914-85-9 N-(4-chlorophenyl)-5-cyano-2-methyl-6-{[2-(2-naphthylamino)-2-oxoethyl]thio}-4-phenyl-1,4-dihydropyridine-3-carboxamide 
• 374771-83-2 5-cyano-4-(2-furyl)-2-methyl-N-(2-methylphenyl)-6-{[2-(2-naphthylamino)-2-oxoethyl]thio}-1,4-dihydropyridine-3-carboxamide 
• 1392572-97-2 C₂₀H₁₃N₃O₃S 
• 1310561-71-7 N-(naphthalen-2-yl)-2-(4-((2,4,6-trioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide 
• 1310561-86-4 2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)-N-(naphthalen-2-yl)acetamide 
• 1266715-62-1 (Z)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-N-(naphthalen-2-yl)acetamide 
• 125983-81-5 2-(4-Acetylamino-phenylamino)-N-naphthalen-2-yl-2-thioxo-acetamide 
• 125983-80-4 2-(4-Amino-phenylamino)-N-naphthalen-2-yl-2-thioxo-acetamide 
• 326913-77-3 C₂₈H₂₄N₆S 
• 326913-73-9 C₂₆H₁₈ClN₅S 
• 326913-75-1 C₂₇H₂₁N₅OS 

Relevant articles and documents

Novel selective ido1 inhibitors with isoxazolo[5,4-d]pyrimidin-4(5h)-one scaffold

Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target in immunomodulation of several pathological conditions, especially cancers. Here we present the synthesis of a series of IDO1 inhibitors with the novel isoxazolo[5,4-d]pyrimidin-4(5H)-one scaffold. A focused library was prepared using a 6-or 7-step synthetic procedure to allow a systematic investigation of the structure-activity relationships of the described scaffold. Chemistry-driven modifications lead us to the discovery of our best-in-class inhibitors possessing p-trifluoromethyl (23), p-cyclohexyl (32), or p-methoxycarbonyl (20, 39) substituted aniline moieties with IC50 values in the low micromolar range. In addition to hIDO1, compounds were tested for their inhibition of indoleamine 2,3-dioxygenase 2 and tryptophan dioxygenase, and found to be selective for hIDO1. Our results thus demon-strate a successful study on IDO1-selective isoxazolo[5,4-d]pyrimidin-4(5H)-one inhibitors, defining promising chemical probes with a novel scaffold for further development of potent small-molecule immunomodulators.

Hydrophobic substituents on isatin derivatives enhance their inhibition against bacterial peptidoglycan glycosyltransferase activity

Moenomycin A, the well-known natural product inhibitor of peptidoglycan glycosyltransferase (PGT), is a large amphiphilic molecule of molecular mass of 1583 g/mol and its bioavailablity as a drug is relatively poor. In searching for small-molecule ligands

CYP enzymes, expressed within live human suspension cells, are superior to widely-used microsomal enzymes in identifying potent CYP1A1/CYP1B1 inhibitors: Identification of quinazolinones as CYP1A1/CYP1B1 inhibitors that efficiently reverse B[a]P toxicity and cisplatin resistance

Microsomal cytochrome P450 (CYP) enzymes, isolated from recombinant bacterial/insect/yeast cells, are extensively used for drug metabolism studies. However, they may not always portray how a developmental drug would behave in human cells with intact intracellular transport mechanisms. This study emphasizes the usefulness of human HEK293 kidney cells, grown in ‘suspension’ for expression of CYPs, in finding potent CYP1A1/CYP1B1 inhibitors, as possible anticancer agents. With live cell-based assays, quinazolinones 9i/9b were found to be selective CYP1A1/CYP1B1 inhibitors with IC50 values of 30/21 nM, and > 150-fold selectivity over CYP2/3 enzymes, whereas they were far less active using commercially-available CYP1A1/CYP1B1 microsomal enzymes (IC50, >10/1.3–1.7 μM). Compound 9i prevented CYP1A1-mediated benzo[a]pyrene-toxicity in normal fibroblasts whereas 9b completely reversed cisplatin resistance in PC-3/prostate, COR-L23/lung, MIAPaCa-2/pancreatic and LS174T/colon cancer cells, underlining the human-cell-assays’ potential. Our results indicate that the most potent CYP1A1/CYP1B1 inhibitors would not have been identified if one had relied merely on microsomal enzymes.