U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C13H9N
Molecular Weight 179.2173
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-AZAPHENANTHRENE

SMILES

C1=CC=C2C(C=CC3=C2N=CC=C3)=C1

InChI

InChIKey=WZJYKHNJTSNBHV-UHFFFAOYSA-N
InChI=1S/C13H9N/c1-2-6-12-10(4-1)7-8-11-5-3-9-14-13(11)12/h1-9H

HIDE SMILES / InChI

Molecular Formula C13H9N
Molecular Weight 179.2173
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Cyclometalated organoplatinum(II) complexes: first example of a monodentate benzo[h]quinolyl ligand and a complex with bridging bis(diphenylphosphino)ethane.
2010-12-21
A domino synthesis of benzoquinolinamide in the presence of iodine.
2010-11-07
Oxidation of a cyclometalated Pd(II) dimer with "CF3+": formation and reactivity of a catalytically competent monomeric Pd(IV) aquo complex.
2010-10-20
pH dependence of binding benzo[h]quinoline and humic acid and effects on fluorescence quenching.
2010-08
Cyclometalated Ir(III) complexes with substituted 1,10-phenanthrolines: a new class of efficient cationic organometallic second-order NLO chromophores.
2010-04-26
Pd(II)-promoted direct cross-coupling reaction of arenes via highly regioselective aromatic C-H activation: a theoretical study.
2010-04-07
Cyclometalated cluster complex with a butterfly-shaped Pt2Ag2 core.
2010-03-15
Structure, photophysical and electrochemical properties, biomolecular interactions, and intracellular uptake of luminescent cyclometalated iridium(III) dipyridoquinoxaline complexes.
2010-03-01
2-Chloro-benzo[h]quinoline-3-carbaldehyde.
2009-10-10
Complete genome sequence of Dyadobacter fermentans type strain (NS114).
2009-09-24
Assessment of azaarenes and azaarones (oxidized azaarene derivatives) in the Dutch coastal zone of the North Sea.
2009-08
Mechanism of benzoquinone-promoted palladium-catalyzed oxidative cross-coupling reactions.
2009-07-22
Synthesis and cytotoxic activity of 5,6-heteroaromatically annulated pyridine-2,4-diamines.
2009-07-01
Determination of basic azaarenes in aviation kerosene by solid-phase extraction and HPLC-fluorescence detection.
2009-06
Benzo(h)quinoline derivatives as G-quadruplex binding agents.
2009-03-15
Synthesis of novel benzo[h]quinolines: wound healing, antibacterial, DNA binding and in vitro antioxidant activity.
2009-03
Luminescent cyclometalated iridium(III) polypyridine indole complexes--synthesis, photophysics, electrochemistry, protein-binding properties, cytotoxicity, and cellular uptake.
2009-01-19
N-heterocyclization of naphthylamines with 1,2- and 1,3-diols catalyzed by an iridium chloride/BINAP system.
2009-01-16
Emissive Pt(II) complexes bearing both cyclometalated ligand and 2-pyridyl hexafluoropropoxide ancillary chelate.
2008-12-28
Novel beta-cyclodextrin modified organic polymeric monolithic substrate for solid phase extraction-room temperature phosphorescence.
2008-12
Complexes of platinum(II) containing ferrocenylethynyl ligands: synthesis, characterization and spectroscopic and electrochemical properties.
2008-09-28
Spectroscopy and electrochemical properties of a homologous series of acetylacetonato and hexafluoroacetylacetonato cyclopalladated and cycloplatinated complexes.
2008-08-28
New benzo[h]quinoline-based ligands and their pincer Ru and Os complexes for efficient catalytic transfer hydrogenation of carbonyl compounds.
2008
Synthesis, photophysical and electrochemical properties, and protein-binding studies of luminescent cyclometalated iridium(III) bipyridine estradiol conjugates.
2007
Toxic effects and oxidative stress in higher plants exposed to polycyclic aromatic hydrocarbons and their N-heterocyclic derivatives.
2006-12
Neutral Ru(II)-based emitting materials: a prototypical study on factors governing radiationless transition in phosphorescent metal complexes.
2006-10-02
Effects of N-heterocyclic polyaromatic hydrocarbons on survival, reproduction, and biochemical parameters in Daphnia magna.
2006-08
Nitrogen-substitution effect on in vivo mutagenicity of chrysene.
2005-09-05
4-Chlorobenzo[F]isoquinoline (CBIQ), a novel activator of CFTR and DeltaF508 CFTR.
2005-06-01
Fungal biotransformation of benzo[f]quinoline, benzo[h]quinoline, and phenanthridine.
2005-05
Isolation and taxonomic affiliation of N-heterocyclic aromatic hydrocarbon-transforming bacteria.
2005-05
Theoretical study of aza-polycyclic aromatic hydrocarbons (aza-PAHs), modelling carbocations from oxidized metabolites and their covalent adducts with representative nucleophiles.
2005-04-07
Mono- and binuclear cyclometallated palladium(II) complexes containing bridging (N,O-) and terminal (N-) imidate ligands: air stable, thermally robust and recyclable catalysts for cross-coupling processes.
2004-12-07
In vivo mutagenicity of benzo[f]quinoline, benzo[h]quinoline, and 1,7-phenanthroline using the lacZ transgenic mice.
2004-04-11
Estimation of kinetic parameter for the biotransformation of three-ring azaarenes by the phenanthrene-degrading strain Sphingomonas sp. LH128.
2004-02
New luminescent cyclometalated iridium(III) diimine complexes as biological labeling reagents.
2003-10-20
Mechanisms of anion secretion in Calu-3 human airway epithelial cells by 7,8-benzoquinoline.
2003-09
Bicarbonate-dependent chloride secretion in Calu-3 epithelia in response to 7,8-benzoquinoline.
2003-08-15
Reaction of alpha-oxoketene-N,S-arylaminoacetals with Vilsmeier reagents: an efficient route to highly functionalized quinolines and their benzo/hetero-fused analogues.
2003-05-16
Benzoquinolines and chloride secretion in murine colonic epithelium.
2003-04
Activation of the human Ah receptor by aza-polycyclic aromatic hydrocarbons and their halogenated derivatives.
2003-04
Phenanthrolines--a new class of CFTR chloride channel openers.
2001-10
Degradation of phenanthrene-analogue azaarenes by Mycobacterium gilvum strain LB307T under aerobic conditions.
2001-08
Crowded Cu(I) complexes involving benzo[h]quinoline: pi-stacking effects and long-lives excited states.
2001-07-02
Cytochrome P450 induction by nitrated polycyclic aromatic hydrocarbons, azaarenes, and binary mixtures in fish hepatoma cell line PLHC-1.
2001-01
Drug metabolizing enzyme induction by benzoquinolines, acridine, and quinacrine; tricyclic aromatic molecules containing a single heterocyclic nitrogen.
1996
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:53:27 GMT 2025
Edited
by admin
on Mon Mar 31 18:53:27 GMT 2025
Record UNII
8KWJ7WT6Y7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-AZAPHENANTHRENE
Systematic Name English
NSC-16033
Preferred Name English
BENZO(H)QUINOLINE
Systematic Name English
7,8-BENZOQUINOLINE
Common Name English
NAPHTHOQUINOLINE, .ALPHA.-
Common Name English
7,8-BENZO(H)QUINOLINE
Common Name English
.ALPHA.-NAPHTHOQUINOLINE
Common Name English
.ALPHA.-BENZOQUINOLINE
Common Name English
Code System Code Type Description
PUBCHEM
9191
Created by admin on Mon Mar 31 18:53:27 GMT 2025 , Edited by admin on Mon Mar 31 18:53:27 GMT 2025
PRIMARY
NSC
16033
Created by admin on Mon Mar 31 18:53:27 GMT 2025 , Edited by admin on Mon Mar 31 18:53:27 GMT 2025
PRIMARY
FDA UNII
8KWJ7WT6Y7
Created by admin on Mon Mar 31 18:53:27 GMT 2025 , Edited by admin on Mon Mar 31 18:53:27 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-937-0
Created by admin on Mon Mar 31 18:53:27 GMT 2025 , Edited by admin on Mon Mar 31 18:53:27 GMT 2025
PRIMARY
EPA CompTox
DTXSID1075199
Created by admin on Mon Mar 31 18:53:27 GMT 2025 , Edited by admin on Mon Mar 31 18:53:27 GMT 2025
PRIMARY
CAS
230-27-3
Created by admin on Mon Mar 31 18:53:27 GMT 2025 , Edited by admin on Mon Mar 31 18:53:27 GMT 2025
PRIMARY