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

Details

Stereochemistry ACHIRAL
Molecular Formula C9H11N
Molecular Weight 133.1903
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1,2,3,4-TETRAHYDROQUINOLINE

SMILES

C1CNC2=CC=CC=C2C1

InChI

InChIKey=LBUJPTNKIBCYBY-UHFFFAOYSA-N
InChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2

HIDE SMILES / InChI

Molecular Formula C9H11N
Molecular Weight 133.1903
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Moexipril and left ventricular hypertrophy.
2007
Development of pinene-derived N,P ligands and their utility in catalytic asymmetric hydrogenation.
2007 Dec 21
Effect of ecdysone receptor gene switch ligands on endogenous gene expression in 293 cells.
2007 Nov
Heteroarotinoids with anti-cancer activity against ovarian cancer cells.
2007 Oct 24
Selective androgen receptor modulators in preclinical and clinical development.
2008
Gold-catalyzed synthesis of chroman, dihydrobenzofuran, dihydroindole, and tetrahydroquinoline derivatives.
2008
Synthesis and characterization of 5,6,7,8-tetrahydroquinoline C5a receptor antagonists.
2008 Apr 15
Natural products as an inspiration in the diversity-oriented synthesis of bioactive compound libraries.
2008 Aug
Bis(1,2,3,4-tetra-hydro-quinolin-6-yl)methane.
2008 Aug 13
Ruthenium-catalyzed enantioselective carbon-carbon bond forming reaction via allenylidene-ene process: synthetic approach to chiral heterocycles such as chromane, thiochromane, and 1,2,3,4-tetrahydroquinoline derivatives.
2008 Aug 13
QSAR study on tetrahydroquinoline analogues as plasmodium protein farnesyltransferase inhibitors: a comparison of rationales of malarial and mammalian enzyme inhibitory activities for selectivity.
2008 Dec
Strictosidine synthase: mechanism of a Pictet-Spengler catalyzing enzyme.
2008 Jan 16
Suzuki-Miyaura approach to JNJ-26076713, an orally active tetrahydroquinoline-containing alphaVbeta3/alphaVbeta5 integrin antagonist. enantioselective synthesis and stereochemical studies.
2008 Mar 21
Air-stable and phosphine-free iridium catalysts for highly enantioselective hydrogenation of quinoline derivatives.
2008 Nov 20
Lewis acid or Brønsted acid catalyzed reactions of vinylidene cyclopropanes with activated carbon-nitrogen, nitrogen-nitrogen, and iodine-nitrogen double-bond-containing compounds.
2009
Self-assembly of hydrogensquarates: crystal structures and properties.
2009 Apr 2
Design and synthesis of indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives as novel HCV inhibitors.
2009 Aug 1
Gold-catalyzed intramolecular allylic amination of 2-tosylaminophenylprop-1-en-3-ols. A concise synthesis of (+/-)-angustureine.
2009 Aug 21
Tetrahydroquinoline derivatives as CRTH2 antagonists.
2009 Dec 15
Easy access to isoquinolines and tetrahydroquinolines from ketoximes and alkynes via rhodium-catalyzed C-H bond activation.
2009 Dec 18
Substituted 1,2,3,4-tetrahydroquinolin-6-yloxypropanes as beta3-adrenergic receptor agonists: design, synthesis, biological evaluation and pharmacophore modeling.
2009 Jan 15
Improved asymmetric synthesis of 3,4-dihydro-2-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-5-[3-(trifluoromethoxy)phenyl]-alpha-(trifluoromethyl)-1(2H)-quinolineethanol, a potent cholesteryl ester transfer protein inhibitor.
2009 Jul 2
Synthesis and biotransformation of tetrahydroquinoline by Mortierella isabelina.
2009 Mar-Apr
Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1,2,3,4-tetrahydroquinoline platform.
2009 May 1
Tetrahydroquinoline sulfonamides as vasopressin 1b receptor antagonists.
2009 Nov 1
N,1-Bis(4-chloro-2-methyl-benz-yl)-3-methyl-2-oxo-1,2,3,4-tetra-hydro-quinoline-3-carboxamide.
2009 Nov 14
Design, synthesis and anticancer evaluation of novel tetrahydroquinoline derivatives containing sulfonamide moiety.
2009 Oct
Substituted tetrahydroquinolines as potent allosteric inhibitors of reverse transcriptase and its key mutants.
2009 Sep 1
A small-molecule oxocarbazate inhibitor of human cathepsin L blocks severe acute respiratory syndrome and ebola pseudotype virus infection into human embryonic kidney 293T cells.
2010 Aug
5,8-Dimeth-oxy-2-phenyl-1,4-dihydro-quinoline-3-carbonitrile.
2010 Aug 18
(3S)-2-Benzyl-3-carb-oxy-1,2,3,4-tetra-hydro-isoquinolinium chloride monohydrate.
2010 Dec 24
Zn(OTf)2-catalyzed reactions of ethenetricarboxylates with 2-aminobenzaldehydes leading to tetrahydroquinoline derivatives.
2010 Feb 19
Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid.
2010 Feb 5
Quinaphos and Dihydro-Quinaphos phosphine-phosphoramidite ligands for asymmetric hydrogenation.
2010 Jul 5
Palladium-catalyzed ring-expansion reaction of indoles with alkynes: from indoles to tetrahydroquinoline derivatives under mild reaction conditions.
2010 Jun 1
Novel tetrahydrochinoline derived CETP inhibitors.
2010 Mar 1
Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles.
2010 Mar 31
Diphosphine-catalyzed mixed double-Michael reaction: a unified synthesis of indolines, dihydropyrrolopyridines, benzimidazolines, tetrahydroquinolines, tetrahydroisoquinolines, dihydrobenzo-1,4-oxazines, and dihydrobenzo-3,1-oxazines.
2010 Mar 5
Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents.
2010 May
Assessment of species specificity of moulting accelerating compounds in Lepidoptera: comparison of activity between Bombyx mori and Spodoptera littoralis by in vitro reporter and in vivo toxicity assays.
2010 May
Asymmetric three-component inverse electron-demand aza-Diels-Alder reaction: efficient synthesis of ring-fused tetrahydroquinolines.
2010 May 17
Diverse effects on mitochondrial and nuclear functions elicited by drugs and genetic knockdowns in bloodstream stage Trypanosoma brucei.
2010 May 4
Highly efficient synthesis and characterization of the GPR30-selective agonist G-1 and related tetrahydroquinoline analogs.
2010 May 7
Synthesis, testing and structure-activity studies on a library of 5-HT₄ ligands.
2010 Nov
Comparison of the activity of non-steroidal ecdysone agonists between dipteran and lepidopteran insects, using cell-based EcR reporter assays.
2010 Nov
Functional importance of tyrosine 294 and the catalytic selectivity for the bis-Fe(IV) state of MauG revealed by replacement of this axial heme ligand with histidine .
2010 Nov 16
InCl3-catalyzed allylic Friedel-Crafts reactions toward the stereocontrolled synthesis of 1,2,3,4-tetrahydroquinolines.
2010 Nov 5
Preparation of half-metallocenes of thiophene-fused and tetrahydroquinoline-linked cyclopentadienyl ligands for ethylene/α-olefin copolymerization.
2010 Nov 7
Quinoline-based compounds as modulators of HIV transcription through NF-kappaB and Sp1 inhibition.
2010 Sep
Enantioselective organocatalytic C-H bond functionalization via tandem 1,5-hydride transfer/ring closure: asymmetric synthesis of tetrahydroquinolines.
2010 Sep 1
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:51:35 GMT 2023
Edited
by admin
on Fri Dec 15 17:51:35 GMT 2023
Record UNII
CCR50N1Z9G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1,2,3,4-TETRAHYDROQUINOLINE
Systematic Name English
NSC-15311
Code English
1,2,3,4-HYDROQUINOLINE
Common Name English
QUINOLINE, 1,2,3,4-TETRAHYDRO-
Systematic Name English
KUSOL
Brand Name English
Code System Code Type Description
CHEBI
213323
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY
FDA UNII
CCR50N1Z9G
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY
CAS
635-46-1
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY
PUBCHEM
69460
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
211-237-6
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY
WIKIPEDIA
Tetrahydroquinoline
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY
MESH
C542964
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY
NSC
15311
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID8060903
Created by admin on Fri Dec 15 17:51:35 GMT 2023 , Edited by admin on Fri Dec 15 17:51:35 GMT 2023
PRIMARY