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174823

Sigma-Aldrich

4-Quinolinecarboxylic acid

97%

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Empirical Formula (Hill Notation):
C10H7NO2
CAS Number:
Molecular Weight:
173.17
Beilstein/REAXYS Number:
5224
EC Number:
MDL number:
PubChem Substance ID:

assay

97%

mp

254-255 °C (lit.)

SMILES string

OC(=O)c1ccnc2ccccc12

InChI

1S/C10H7NO2/c12-10(13)8-5-6-11-9-4-2-1-3-7(8)9/h1-6H,(H,12,13)

InChI key

VQMSRUREDGBWKT-UHFFFAOYSA-N

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1 of 4

This Item
108340246395633658
vibrant-m

174823

4-Quinolinecarboxylic acid

vibrant-m

246395

4-Hydrazinobenzoic acid

vibrant-m

633658

4-Thiazolecarboxylic acid

assay

97%

assay

97%

assay

97%

assay

97%

mp

254-255 °C (lit.)

mp

267-268 °C (lit.)

mp

218 °C (dec.) (lit.)

mp

195-199 °C (lit.)

Application

4-Quinolinecarboxylic acid was used in the coupling reaction with diamine linker. A 4-quinolinecarboxylic acid analogue, brequinar sodium was used to inhibit dihydroorotate dehydrogenase and the de novo biosynthesis of pyrimidine.

Biochem/physiol Actions

4-Quinolinecarboxylic acid showed anti-tumor activity against L1210 leukemia and B16 melanoma.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Solid-phase synthesis of substituted quinoline and isoquinoline derivatives using heterocyclic N-oxide chemistry.
Tetrahedron Letters, 39(27), 4749-4752 (1998)
He Huang et al.
The Journal of organic chemistry, 74(15), 5476-5480 (2009-07-04)
We developed a simple and convenient copper-catalyzed method for the synthesis of quinoline-2-carboxylate derivatives through sequential intermolecular addition of alkynes onto imines and subsequent intramolecular ring closure by arylation. The efficiency of this system allowed the reactions to be carried
D L Dexter et al.
Cancer research, 45(11 Pt 1), 5563-5568 (1985-11-01)
A novel, substituted 4-quinolinecarboxylic acid (NSC 339768) demonstrated antitumor activity against L1210 leukemia and B16 melanoma in the National Cancer Institute's Developmental Therapeutics Program. An extensive analogue synthesis program was initiated; over 200 derivatives were synthesized and tested for anticancer
Afshin Zarghi et al.
Bioorganic & medicinal chemistry, 17(14), 5312-5317 (2009-06-30)
A group of 4-carboxyl quinoline derivatives possessing a methylsulfonyl COX-2 pharmacophore at the para position of the C-2 phenyl ring were designed and synthesized as selective COX-2 inhibitors. In vitro COX-1/COX-2 structure-activity relationships were determined by varying the substituents on
The cardiovascular and respiratory effects of 3-hydroxy-2-phenyl cinchoninic acid.
H A WALKER et al.
The Journal of pharmacology and experimental therapeutics, 102(2), 71-78 (1951-06-01)

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