18472-03-2

Basic information

• Product Name: TIMTEC-BB SBB006414
• Synonyms: TIMTEC-BB SBB006414;5-CHLORO-7-NITRO-8-QUINOLINOL;5-chloro-7-nitroquinolin-8-ol
• CAS NO: 18472-03-2
• Molecular Formula: C₉H₅ClN₂O₃
• Molecular Weight: 224.6
• Mol File: 18472-03-2.mol

Chemical Properties

• Boiling Point: 371.9°C at 760 mmHg
• Flash Point: 178.7°C
• Appearance: /
• Density: 1.615g/cm³
• Vapor Pressure: 4.67E-06mmHg at 25°C
• Refractive Index: 1.73
• CAS DataBase Reference: TIMTEC-BB SBB006414(CAS DataBase Reference)
• NIST Chemistry Reference: TIMTEC-BB SBB006414(18472-03-2)
• EPA Substance Registry System: TIMTEC-BB SBB006414(18472-03-2)

Safety Data

• Hazardous Substances Data: 18472-03-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H5ClN2O3/c10-6-4-7(12(14)15)9(13)8-5(6)2-1-3-11-8/h1-4,13H

Upstream product

• 95-85-2 2-hydroxy-5-chloro-aniline 
• 130-16-5 5-Chloro-8-hydroxyquinoline 

Downstream Products

• 1262633-14-6 N-(8-hydroxyquinolin-7-yl)benzenesulfonamide 
• 1262633-16-8 4-fluoro-N-(8-hydroxyquinolin-7-yl)benzenesulfonamide 
• 1262633-18-0 N-(8-hydroxyquinolin-7-yl)-[1,1'-biphenyl]-4-sulfonamide 
• 940298-42-0 tert-butyl 5-chloro-7-[3-(phenylpyridin-2-ylmethyl)ureido]quinolin-8-yloxycarboxylate 
• 940298-38-4 N-(5-chloro-8-hydroxyquinolin-7-yl)-3,3-diphenylpropionamide 
• 1432063-19-8 N-(5,8-dioxo-2-(4-(trifluoromethyl)phenyl)-5,8-dihydroquinolin-7-yl)acetamide 
• 1432063-30-3 7-amino-2-(4-(trifluoromethyl)phenyl)quinoline-5,8-dione 
• 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 
• 86048-40-0 methyl 5-chloroxazolo <4,5-h> quinoline-2-carboxylate 
• 97000-17-4 5-Chloro-2-phenyl-oxazolo[4,5-h]quinoline 
• 18471-93-7 7-amino-5-chloro-8-hydroxyquinoline 
• 18472-06-5 7-amino-8-hydroxyquinoline 

Relevant articles and documents

Method of preparing Quinoline-5,8-dione derivatives for TGase 2 inhibitor

I Is -5,8- of the quinoline, dione derivative compound. of Formula I, or a stereoisomer or a pharmaceutically acceptable salt thereof, wherein the compound of Formula, TGase 2 has, inhibitory effects TGase 2, and thus the pharmaceutical composition may be useful for preventing or treating disorders or diseases mediated by TGase 2 or inhibiting. (by machine translation)

Quinoline-5,8-dione derivatives for TGase 2 inhibitor, and the pharmaceutical composition comprising the same

The present invention relates to a quinolin-5,8-dione derivative compound represented by chemical formula I, an optical isomer thereof or a pharmaceutically acceptable salt thereof. The compound represented by chemical formula I of the present invention has a TGase 2 inhibitory effect, and the pharmaceutical composition comprising the same can be usefully used for preventing or treating disorders or diseases mediated by TGase 2 or response to TGase 2 inhibition.COPYRIGHT KIPO 2020

Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes

Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.

Synthesis of New Quinolinequinone Derivatives and Preliminary Exploration of their Cytotoxic Properties

A series of 7-amino- and 7-acetamidoquinoline-5,8-diones with aryl substituents at the 2-position were synthesized, characterized, and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1) -directed antitumor agents. The synthesis of lavendamycin analogues is illustrated. Metabolism studies demonstrated that 7-amino analogues were generally better substrates for NQO1 than 7-amido analogues, as were compounds with smaller heteroaromatic substituents at the C-2 position. Surprisingly, only two compounds, 7-acetamido-2-(8′-quinolinyl)quinoline-5,8-dione (11) and 7-amino-2-(2-pyridinyl)quinoline-5,8-dione (23), showed selective cytotoxicity toward the NQO1-expressing MDA468-NQ16 breast cancer cells versus the NQO1-null MDA468-WT cells. For all other compounds, NQO1 protected against quinoline-5,8-dione cytotoxicity. Compound 22 showed potent activity against human breast cancer cells expressing or not expressing NQO1, with respective IC50 values of 190 nM and 140 nM and a low NQO1-mediated reduction rate, which suggests that the mode of action of 22 differs from that of lavendamycin and involves an unidentified target(s).

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.

Identifying chelators for metalloprotein inhibitors using a fragment-based approach

Fragment-based lead design (FBLD) has been used to identify new metal-binding groups for metalloenzyme inhibitors. When screened at 1 mM, a chelator fragment library (CFL-1.1) of 96 compounds produced hit rates ranging from 29% to 43% for five matrix meta

Hydroxyquinoline Derivatives

Compounds of the formula I in which X, Y, R1, R1′, R2, R3 have the meanings indicated in claim 1, are inhibitors of cell proliferation and can be employed for the treatment of tumours.

Preparation of 8-alkyl 7-(2-imidazolinylamino)quinolines via palladium mediated alkylations

A convenient preparation of 8-alkyl substituted 7-(2-imidazo linylamino)quinolines from the corresponding 8-trifluoro-methanesulfonates, utilizing palladium cross-coupling reactions is described.

Method of prevention and treatment of peptic ulcers

Disclosed is a method for prophylactic and therapeutic treatment of peptic ulcers which comprises the administration of a pharmaceutical composition containing a compound of the formula STR1 or a pharmaceutically acceptable salt thereon, wherein 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, aminolakyl, or carboxyalkyl, Z is oxygen, sulfur or nitrogen, X is cyano, carbalkoxyl, carboxyl, formuloximino, tetrazolyl, carbalkoxyalky or caboxyalkyl, and m is 0 or 1, in admixture or in association with a pharmaceutically acceptable carrier.

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.