18471-93-7

Basic information

• Product Name: 8-QUINOLINOL, 7-AMINO-5-CHLORO-
• Synonyms: 8-QUINOLINOL, 7-AMINO-5-CHLORO-;7-amino-5-chloro-8-quinolinol;7-amino-5-chloro-quinolin-8-ol;7-amino-5-chloroquinolin-8-ol
• CAS NO: 18471-93-7
• Molecular Formula: C₉H₇ClN₂O
• Molecular Weight: 194.62
• Mol File: 18471-93-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 162-164 °C(Solv: ethanol (64-17-5))
• Boiling Point: 400.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.503±0.06 g/cm3(Predicted)
• PKA: 3.56±0.30(Predicted)
• CAS DataBase Reference: 8-QUINOLINOL, 7-AMINO-5-CHLORO-(CAS DataBase Reference)
• NIST Chemistry Reference: 8-QUINOLINOL, 7-AMINO-5-CHLORO-(18471-93-7)
• EPA Substance Registry System: 8-QUINOLINOL, 7-AMINO-5-CHLORO-(18471-93-7)

Safety Data

• Hazardous Substances Data: 18471-93-7(Hazardous Substances Data)

Upstream product

• 130-16-5 5-Chloro-8-hydroxyquinoline 
• 18472-03-2 5-chloro-7-nitro-8-hydroxy-quinoline 

Downstream Products

• 940298-38-4 N-(5-chloro-8-hydroxyquinolin-7-yl)-3,3-diphenylpropionamide 
• 940298-42-0 tert-butyl 5-chloro-7-[3-(phenylpyridin-2-ylmethyl)ureido]quinolin-8-yloxycarboxylate 
• 97000-09-4 5-Chloro-2-oxo-oxazolo[4,5-h]quinoline-3-carboxylic acid 2-methoxy-phenyl ester 
• 97000-10-7 5-Chloro-3-[(E)-(3-phenyl-acryloyl)]-3H-oxazolo[4,5-h]quinolin-2-one 
• 97000-17-4 5-Chloro-2-phenyl-oxazolo[4,5-h]quinoline 
• 86048-40-0 methyl 5-chloroxazolo <4,5-h> quinoline-2-carboxylate 

Relevant articles and documents

Substituted oxines inhibit endothelial cell proliferation and angiogenesis

Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial cells, which comprises of a dual inhibition of type 2 human methionine aminopeptidase (MetAP2) and sirtuin 1 (SIRT1). Structure-activity relationship study (SAR) of nitroxoline offered many surprises where minor modifications yielded oxine derivatives with increased potency against human umbilical vein endothelial cells (HUVEC), but with entirely different as yet unknown mechanisms. For example, 5-nitrosoquinolin-8-ol (33) inhibited HUVEC growth with sub-micromolar IC50, but did not affect MetAP2 or MetAP1, and it only showed weak inhibition against SIRT1. Other sub-micromolar inhibitors were derivatives of 5-aminoquinolin-8-ol (34) and 8-sulfonamidoquinoline (32). A sulfamate derivative of nitroxoline (48) was found to be more potent than nitroxoline with the retention of activities against MetAP2 and SIRT1. The bioactivity of the second hit, micromolar HUVEC and MetAP2 inhibitor carbamate 22 was improved further with an SAR study culminating in carbamate 24 which is a nanomolar inhibitor of HUVEC and MetAP2. The Royal Society of Chemistry 2012.

2-Oxo-1,3-oxazolo[4,5-h] quinolines useful as anti-allergy agents

New quinoline compound, and the corresponding 1,2-; 1,3-; and 1,4-benzodiazines, the quinoline compounds being of the formulae: STR1 and salts thereof, wherein R is hydrogen, acyl, carboethoxy,(3-methoxyphen)acetyl,(2-phenyl)propionyl, dimethylcarbamoyl or methyl, R1 and R2 are independently hydrogen, lower alkyl, halo, trifluoromethyl, amino, lower alkyl amino, lower acylamino, cyano, aryl, aryl/lower alkylene, nitro, lower alkynyl, lower alkenyl, lower alkyl sulfinyl, lower alkyl sulfonyl, lower alkoxycarbonyl, carboxyl, lower alkoxy, lower alkanoyl, or lower alkenoyl, Y is oxygen, sulfur, nitrogen or R3 N wherein R3 is hydrogen, lower alkyl, alkenyl, alkynyl, aryl, aralkyl, acyl, aminoalkyl, or carboxyalkyl, Z is oxygen, sulfur or nitrogen, X is cyano, carbalkoxy, carboxyl, formyloximino, tetrazolyl, carbalkoxyalkyl or carboxyalkyl, and m is 0 or 1, are useful as medicinals, especially for treatment of asthma, and/or as intermediates in the preparation of compounds useful for treating asthma.