5467-57-2

Basic information

• Product Name: 2-CHLOROQUINOLINE-4-CARBOXYLIC ACID
• Synonyms: AKOS BB-6908;A-CHLORO CINCHONINIC ACID;2-CHLORO-4-CARBOXY QUINOLINE;2-CHLOROQUINOLINE-4-CARBOXYLIC ACID;2-chloroquinazoline-4-carboxylic acid ethyl ester;4-Quinolinecarboxylic acid, 2-chloro-;Nsc25654;2-Chlorocinchoninic acid
• CAS NO: 5467-57-2
• Molecular Formula: C₁₀H₆ClNO₂
• Molecular Weight: 207.61
• Product Categories: Quinoline series;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines;Haloquinolines;Quinolines;CHIRAL CHEMICALS;Quinoline;Carboxylic Acids;Quinolines, Isoquinolines & Quinoxalines
• Mol File: 5467-57-2.mol

Chemical Properties

• Melting Point: 244 °C
• Boiling Point: 368.7 °C at 760 mmHg
• Flash Point: 176.8 °C
• Appearance: /
• Density: 1.469 g/cm³
• Vapor Pressure: 4.35E-06mmHg at 25°C
• Refractive Index: 1.69
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 2.17±0.10(Predicted)
• CAS DataBase Reference: 2-CHLOROQUINOLINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROQUINOLINE-4-CARBOXYLIC ACID(5467-57-2)
• EPA Substance Registry System: 2-CHLOROQUINOLINE-4-CARBOXYLIC ACID(5467-57-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 5467-57-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloroquinoline-4-carboxylic acid is used as an intermediate in the synthesis of dimethyl(naphthalenecarbonyl)aminobenzoic acids, which are potent and selective EP4 antagonists. These antagonists have potential applications in the treatment of various inflammatory and pain-related conditions, as well as other therapeutic areas.
In the pharmaceutical industry, 2-chloroquinoline-4-carboxylic acid plays a crucial role in the development of new drugs and therapeutic agents. Its unique chemical properties and reactivity make it a valuable building block for the synthesis of complex organic molecules with potential medicinal properties. By using this intermediate, researchers can explore the design and synthesis of novel compounds that target specific biological pathways and receptors, ultimately leading to the discovery of new treatments for various diseases and conditions.

InChI:InChI=1/C10H6ClNO2/c11-9-5-7(10(13)14)6-3-1-2-4-8(6)12-9/h1-5H,(H,13,14)

Upstream product

• 40614-43-5 4-carboxyquinoline 1-oxide 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 
• 4053-40-1 4-methylquinoline 1-oxide 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 91-56-5 indole-2,3-dione 
• 83674-64-0 4-Bromo-2-chloro-quinoline 
• 2258-42-6 formyl acetic anhydride 
• 15733-89-8 2-quinolone-4-carboxylic acid 
• 5467-61-8 ethyl ester of 2-chlorocinchoninic acid 

Downstream Products

• 10222-61-4 2-(n-butyloxy)-4-quinolinecarboxylic acid 
• 854860-95-0 2-phenylsulfanyl-quinoline-4-carboxylic acid 
• 157915-68-9 2-amino-quinoline-4-carboxylic acid 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 
• 16335-07-2 2-Amino-cinchoninsaeureamid 
• 486-74-8 4-quinolinic acid 
• 140455-62-5 3-phenyl-1,2,4-triazolo<4,3-a>quinoline-9-carboxylic acid 
• 137522-63-5 quinolino<2,1-b>quinazolin-12-one-5-carboxylic acid 
• 140455-63-6 1-(3-Hydroxy-phenyl)-[1,2,4]triazolo[4,3-a]quinoline-5-carboxylic acid 
• 140455-60-3 1,2,3,4-tetrazolo<4,3-a>quinoline-9-carboxylic acid 
• 132-60-5 cinchophen 
• 5467-61-8 ethyl ester of 2-chlorocinchoninic acid 
• 87864-14-0 2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) 
• 85-79-0 Dibucaine 

Relevant articles and documents

Quinoline carboxamide core moiety-based compounds inhibit P. falciparum falcipain-2: Design, synthesis and antimalarial efficacy studies

Targeting Falcipain-2 (FP2) for the development of antimalarials is a promising and established concept in antimalarial drug discovery and development. FP2, a member of papain-family cysteine protease of the malaria parasite Plasmodium falciparum holds an important role in hemoglobin degradation pathway. A new series of quinoline carboxamide-based compounds was designed, synthesized and evaluated for antimalarial activity. We integrated molecular hybridization strategy with in-silico drug design to develop FP2 inhibitors. In-vitro results of FP2 inhibition by Qs17, Qs18, Qs20 and Qs21 were found to be in low micromolar range with IC50 4.78, 7.37, 2.14 and 2.64 μM, respectively. Among the 25 synthesized compounds, four compounds showed significant antimalarial activities. These compounds also depicted morphological and food-vacuole abnormalities much better than that of E-64, an established FP2 inhibitor. Overall these aromatic substituted quinoline carboxamides can serve as promising leads for the development of novel antimalarial agents.

Quinoline substituted chalcone compound as well as preparation method and application thereof

The invention discloses a novel quinoline substituted chalcone compound as well as pharmaceutically acceptable salts and a preparation method thereof. The invention further discloses a pharmaceuticalcomposition which comprises a therapeutically effective amount of the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts and a pharmaceutically acceptable carrier. The invention further discloses a tubulin inhibitor which comprises the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts. The invention further disclosesapplication of the novel quinoline substituted chalcone compound and/or the pharmaceutically acceptable salts in preparing drugs for treating but not limited to colon cancer, leukemia, liver cancer, breast cancer and other diseases. The compound in the application shows excellent anti-tumor activity, and has more stable metabolic properties and better druggability prospect.

Discovery of Novel Quinoline-Chalcone Derivatives as Potent Antitumor Agents with Microtubule Polymerization Inhibitory Activity

A series of novel quinoline-chalcone derivatives were designed, synthesized, and evaluated for their antiproliferative activity. Among them, compound 24d exhibited the most potent activity with IC50 values ranging from 0.009 to 0.016 μM in a panel of cancer cell lines. Compound 24d also displayed a good safety profile with an LD50 value of 665.62 mg/kg by intravenous injection, and its hydrochloride salt 24d-HCl significantly inhibited tumor growth in H22 xenograft models without observable toxic effects, which was more potent than that of CA-4. Mechanism studies demonstrated that 24d bound to the colchicine site of tubulin, arrested the cell cycle at the G2/M phase, induced apoptosis, depolarized mitochondria, and induced reactive oxidative stress generation in K562 cells. Moreover, 24d has potent in vitro antimetastasis and in vitro and in vivo antivascular activities. Collectively, our findings suggest that 24d deserves to be further investigated as a potent and safe antitumor agent for cancer therapy.

Design, synthesis and antibacterial activity studies of novel quinoline carboxamide derivatives

A series of novel quinoline-6-carboxamides and 2-chloroquinoline-4- carboxamides were synthesized by the reaction of their analogous carboxylic acids with various amine derivatives in the presence of base TEA and protecting agent BOP at room temperature.

Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents

A series of fused and functionalized pyridine derivatives were designed, synthesized and tested for their potential antitubercular properties. All these novel compounds were prepared by using multistep methods involving the construction of pyridine ring as a key synthetic step. Some of these compounds were found to be interesting when tested for their antitubercular properties in vitro and one of them appeared as an attractive and potential antitubercular agent.

Heteroaryl hydroxycarbonylation: An efficient, robust, practically scalable approach using formyl acetate as the co source

A simple, efficient, regioselective, and scalable palladium-catalyzed hydroxycarbonylation of heteroaryl halides to corresponding carboxylic acids using acetic-formic anhydride in presence of Pd(OAc)2, dppf, and diisopropylethyl amine in dimethyl formamide at 80-90 °C in excellent yields. Taylor & Francis Group, LLC.

HCV INHIBITORS AND METHODS OF USING THEM

The present invention comprises tetrazoloquinoline-compounds that are inhibitors of HCV. Compositions comprising the compounds in combination with a pharmaceutically acceptable carrier are also disclosed, as are methods of using the compounds and composit

Fluorescence properties of 2-substituted 6-, 7- or 8-methoxyquinoline-4-carboxylic acid derivatives

2-Substituted 6-, 7- or 8-methoxyquinoline-4-carboxylic acid derivatives were synthesized. The fluorescence quantum yield (Φ) of these compounds increased in the order, 2-thioxo-, 2-methylthio-, 2-methylsulfinyl-, 2-methylsulfonyl derivatives of 6-methoxyquinoline-4-carboxylic acid. Ethyl 6-methoxy-2-methylsulfonylquinoline-4-carboxylate (Φ(CH3CN) = 0.74 or Φ(EtOH) = 0.69) showed a much higher fluorescence quantum yield than those (Φ(CH3CN) = 0.19 or Φ(EtOH) = 0.19 and Φ(CH3CN) = 0.16 or Φ(EtOH) = 0.05) of the 7- and 8-methoxy derivatives in both acetonitrile and ethanol.