4-AMINOQUINOLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H8N2
Molecular Weight	144.1732
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=C2C=CC=CC2=NC=C1

InChI

InChIKey=FQYRLEXKXQRZDH-UHFFFAOYSA-N

InChI=1S/C9H8N2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H,(H2,10,11)

HIDE SMILES / InChI

Molecular Formula	C9H8N2
Molecular Weight	144.1732
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Interaction of Clostridium botulinum C2 toxin with lipid bilayer membranes and Vero cells: inhibition of channel function by chloroquine and related compounds in vitro and intoxification in vivo.	2001 Jul	11427518
Analysis of the ABCR (ABCA4) gene in 4-aminoquinoline retinopathy: is retinal toxicity by chloroquine and hydroxychloroquine related to Stargardt disease?	2001 Jun	11384574
3D structure of Torpedo californica acetylcholinesterase complexed with huprine X at 2.1 A resolution: kinetic and molecular dynamic correlates.	2002 Mar 5	11863435
Double-drug development against antioxidant enzymes from Plasmodium falciparum.	2003	14962365
Short report: association between chloroquine and amodiaquine resistance and allelic variation in the Plasmodium falciparum multiple drug resistance 1 gene and the chloroquine resistance transporter gene in isolates from the upper Nile in southern Sudan.	2003 Aug	13677373
Hydroxychloroquine is much less active than chloroquine against chloroquine-resistant Plasmodium falciparum, in agreement with its physicochemical properties.	2003 Aug	12837731
Isoquine and related amodiaquine analogues: a new generation of improved 4-aminoquinoline antimalarials.	2003 Nov 6	14584944
Polymorphism in the Plasmodium falciparum chloroquine-resistance transporter protein links verapamil enhancement of chloroquine sensitivity with the clinical efficacy of amodiaquine.	2003 Sep 19	14599295
Synergistic interaction of a chloroquine metabolite with chloroquine against drug-resistant malaria parasites.	2004 Apr 1	15013850
Application of multi-component reactions to antimalarial drug discovery. Part 1: Parallel synthesis and antiplasmodial activity of new 4-aminoquinoline Ugi adducts.	2004 Aug 2	15225694
A correlation study of quinoline derivatives and their pharmaceutical behavior by ab initio calculated NQR parameters.	2004 Mar	15368921
Molecular analysis of Plasmodium falciparum from drug treatment failure patients in Papua New Guinea.	2004 Mar	15031512
Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs.	2004 Mar 5	14967191
A new class of nonpeptide bradykinin B(2) receptor ligand, incorporating a 4-aminoquinoline framework. Identification of a key pharmacophore to determine species difference and agonist/antagonist profile.	2004 May 6	15115408
Parallel synthesis and antimalarial screening of a 4-aminoquinoline library.	2004 May-Jun	15132606
In vitro inhibition of severe acute respiratory syndrome coronavirus by chloroquine.	2004 Oct 8	15351731
1,4-bis(3-aminopropyl)piperazine libraries: from the discovery of classical chloroquine-like antimalarials to the identification of new targets.	2005 Feb	15720196
Synthesis of ring-substituted 4-aminoquinolines and evaluation of their antimalarial activities.	2005 Feb 15	15686903
Design and synthesis of new antimalarial agents from 4-aminoquinoline.	2005 Mar 15	15727868
A medicinal chemistry perspective on 4-aminoquinoline antimalarial drugs.	2006	16719804
Application of multicomponent reactions to antimalarial drug discovery. Part 2: New antiplasmodial and antitrypanosomal 4-aminoquinoline gamma- and delta-lactams via a 'catch and release' protocol.	2006 Aug 15	16690319
Probing the role of the covalent linkage of ferrocene into a chloroquine template.	2006 Jul 27	16854077
Susceptibility of Colombian Plasmodium falciparum isolates to 4-aminoquinolines and the definition of amodiaquine resistance in vitro.	2006 May	16862335
Genotoxicity of chloroquine in rat liver cells: protective role of free radical scavengers.	2006 May	16532284
The use of antirheumatic disease drugs during pregnancy.	2006 Nov	19804006
Rapid selection of dhfr mutant allele in Plasmodium falciparum isolates after the introduction of sulfadoxine/pyrimethamine in combination with 4-aminoquinolines in Papua New Guinea.	2006 Nov	16600696
4-Aminoquinoline melanin-concentrating hormone 1-receptor (MCH1R) antagonists.	2006 Oct 15	16919453
Fujita-Ban QSAR analysis and CoMFA study of quinoline antagonists of immunostimulatory CpG-oligodeoxynucleotides.	2007 Jan 1	17049254
Synthesis and antimalarial activity of side chain modified 4-aminoquinoline derivatives.	2007 Jan 25	17228883
In vitro activity of ferroquine (SSR 97193) against Plasmodium falciparum isolates from the Thai-Burmese border.	2007 Jun 27	17597537
Exploration of rate-limiting conformational state for 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N(omega)-oxides (tebuquine analogues) for antimalarial activity using molecular shape analysis and molecular field analysis studies.	2007 May-Jun	17425301
Design, synthesis and in vitro antitumor activity of 4-aminoquinoline and 4-aminoquinazoline derivatives targeting EGFR tyrosine kinase.	2008 Aug 15	18678492
Antiplasmodial, beta-haematin inhibition, antitrypanosomal and cytotoxic activity in vitro of novel 4-aminoquinoline 2-imidazolines.	2008 Dec 7	19005606
[Urotensin II promotes atherosclerosis].	2008 Jan	18277587
Chronic urotensin II infusion enhances macrophage foam cell formation and atherosclerosis in apolipoprotein E-knockout mice.	2008 Oct	18806619
Synthesis and antimalarial activity of novel side chain modified antimalarial agents derived from 4-aminoquinoline.	2008 Sep	18782041
Synthesis and antimalarial activity of new amino analogues of amodiaquine.	2008 Sep	18782038
Antimalarial activities of ferroquine conjugates with either glutathione reductase inhibitors or glutathione depletors via a hydrolyzable amide linker.	2009 Dec 1	19864147

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:10:37 GMT 2023` Edited by `admin` on `Fri Dec 15 17:10:37 GMT 2023`
Record UNII	GTE5P5L97N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4-AMINOQUINOLINE

Systematic Name

English

QUINOLINE, 4-AMINO-

Systematic Name

English

4-QUINOLYLAMINE

Systematic Name

English

4-QUINOLINAMINE

Systematic Name

English

4-AMINOQUINOLINE [VANDF]

Common Name

English

Code System Code Type Description

FDA UNII

GTE5P5L97N