103914-52-9

Basic information

• Product Name: 2-(4-BROMO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID
• Synonyms: AKOS AUF0509;2-(4-BROMO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID;TIMTEC-BB SBB001346;2-(4-bromophenyl)cinchoninic acid;4-Quinolinecarboxylic acid, 2-(4-bromophenyl)-;AIDS110143;AIDS-110143;AK-968/37166242
• CAS NO: 103914-52-9
• Molecular Formula: C₁₆H₁₀BrNO₂
• Molecular Weight: 328.16
• Mol File: 103914-52-9.mol

Chemical Properties

• Boiling Point: 497.7 °C at 760 mmHg
• Flash Point: 254.8 °C
• Appearance: /
• Density: 1.556 g/cm³
• Vapor Pressure: 1.01E-10mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(4-BROMO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID(103914-52-9)
• EPA Substance Registry System: 2-(4-BROMO-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID(103914-52-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 103914-52-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
2-(4-Bromo-phenyl)-quinoline-4-carboxylic acid is used as a pharmaceutical candidate for its potential biological activities. Its unique structure allows it to be a promising agent in the development of new drugs, targeting various diseases and conditions.
Used in Organic Synthesis:
2-(4-Bromo-phenyl)-quinoline-4-carboxylic acid is used as a starting material or intermediate in the synthesis of other organic compounds. Its versatile structure enables the creation of a wide range of chemical products, contributing to the advancement of organic chemistry.
Used in Scientific Research:
2-(4-Bromo-phenyl)-quinoline-4-carboxylic acid is used as a research tool in various scientific fields, including chemistry, biology, and materials science. Its unique properties and potential applications make it a valuable compound for studying and understanding complex chemical and biological processes.

InChI:InChI=1/C16H10BrNO2/c17-11-7-5-10(6-8-11)15-9-13(16(19)20)12-3-1-2-4-14(12)18-15/h1-9H,(H,19,20)/p-1

Upstream product

• 91-56-5 indole-2,3-dione 
• 99-90-1 para-bromoacetophenone 

Downstream Products

• 345902-20-7 4-amino-2-(4'-bromophenyl)quinoline 
• 351899-02-0 2-(4-bromophenyl)quinoline-4-carboxylic acid hydrazide 
• 859929-64-9 2-(4-bromo-phenyl)-quinoline-4-carbonyl azide 
• 856086-95-8 [2-(4-bromo-phenyl)-[4]quinolyl]-carbamic acid ethyl ester 
• 19155-99-8 [6,8-dichloro-2-(4-chloro-phenyl)-[4]quinolyl]-[2]piperidyl-methanol 
• 148887-85-8 {[2-(4-Bromo-phenyl)-quinoline-4-carbothioyl]-methyl-amino}-acetic acid ethyl ester 
• 103914-53-0 2-(4-bromophenyl)-4-quinolinecarbonyl chloride 
• 351982-02-0 ethyl 2-(4'-bromophenyl)-quinoline-4-carboxylate 
• 148887-72-3 {[2-(4-Bromo-phenyl)-quinoline-4-carbonyl]-methyl-amino}-acetic acid ethyl ester 
• 24641-31-4 2-(4-bromophenyl)quinoline 
• 6952-34-7 2-(4-hydroxyphenyl)-quinoline-4-carboxylic acid 

Relevant articles and documents

Synthesis and Luminescent Properties of Eu3+, Gd3+, and Tb3+ Complexes with Quinoline-4-carboxylic Acids

New complex compounds LnL3·nH2O (n = 5–10) have been synthesized on the basis of Eu3+, Gd3+, and Tb3+ salts and quinoline-4-carboxylic acid derivatives obtained via the Pfitzinger reaction. Compositio

A diboronic acid fluorescent sensor for selective recognition of d-ribose via fluorescence quenching

Boronic acids have been widely developed as fluorescent sensors for recognition of carbohydrates, especially d-glucose, ions, catechol compounds and so on. However, few d-ribose selective boronic acid sensors have been reported, and their poor water solub

A highly selective and sensitive boronic acid-based sensor for detecting Pd2+ ion under mild conditions

Herein, a boronic acid-based sensor was reported selectively to recognize Pd2+ ion. The fluorescence intensity increased 36-fold after sensor binding with 2.47 × 10?5 M of Pd2+ ion. It was carried out in the 99% aqueous so

New quinoline-based heterocycles as anticancer agents targeting Bcl-2

The Bcl-2 protein has been studied as an anticancer drug target in recent years, due to its gatekeeper role in resisting programmed cancer cell death (apoptosis), and the design of BH3 domain mimetics has led to the clinical approval of Venetoclax (ABT-19

Synthesis of Novel Quinoline–Benzoxazolinone Ester Hybrids: In Vitro Anti-Inflammatory Activity and Antibacterial Activity

Abstract: A series of novel quinoline-benzoxazolinone ester hybrids were synthesized characterized and assessed for their in vitro anti-inflammatory and antibacterial activity. The in vitro anti-inflammatory activity was executed using protein denaturation assay, proteinase inhibitory assay and human red blood cell membrane stabilization assay. Most of the compounds exhibited potential anti-inflammatory activity. Compound (2-oxobenzo[d]oxazol-3(2H)-yl)methyl-2-(thiophen-2-yl)quinoline-4-carboxylate showed a better anti-inflammatory activity than the standard drugs diclofenac sodium and indomethacin. Furthermore, antibacterial activities of the synthesized compounds were evaluated using resazurin microtiter assay (REMA) and were compared with a positive drug standard chloramphenicol. The compounds demonstrated moderate to potent antibacterial activity. (2-Oxobenzo[d]oxazol-3(2H)-yl)methyl-2-(3,4-dimethoxyphenyl)quinoline-4-carboxylate and (2-oxobenzo[d]oxazol-3(2H)-yl)methyl-2-(2-chlorophenyl)quinoline-4-carboxylate displayed excellent activity against all bacterial strains in comparison to standard chloramphenicol. Moreover, cytotoxicity was performed on MDCK cells using MTT assay and it was found that none of the synthesized derivatives possessed any cytotoxicity.

Synthesis, characterization, and antileishmanial activity of certain quinoline-4-carboxylic acids

Leishmaniasis is a fatal neglected parasitic disease caused by protozoa of the genus Leishmania and transmitted to humans by different species of phlebotomine sandflies. The disease incidence continues to increase due to lack of vaccines and prophylactic drugs. Drugs commonly used for the treatment are frequently toxic and highly expensive. The problem of these drugs is further complicated by the development of resistance. Thus, there is an urgent need to develop new antileishmanial drug candidates. The aim of this study was to synthesize certain quinoline-4-carboxylic acids, confirm their chemical structures, and evaluate their antileishmanial activity. Pfitzinger reaction was employed to synthesize fifteen quinoline-4-carboxylic acids (Q1-Q15) by reacting equimolar mixtures of isatin derivatives and appropriate α-methyl ketone. The products were purified, and their respective chemical structures were deduced using various spectral tools (IR, MS, 1H NMR, and 13C NMR). Then, they were investigated against L. donovani promastigote (clinical isolate) in different concentration levels (200 μg/mL to 1.56 μg/mL) against sodium stibogluconate and amphotericin B as positive controls. The IC50 for each compound was determined and manipulated statistically. Among these compounds, Q1 (2-methylquinoline-4-carboxylic acid) was found to be the most active in terms of IC50.

Design, Synthesis, and Biological Evaluation of 4-Quinoline Carboxylic Acids as Inhibitors of Dihydroorotate Dehydrogenase

We pursued a structure-guided approach toward the development of improved dihydroorotate dehydrogenase (DHODH) inhibitors with the goal of forming new interactions between DHODH and the brequinar class of inhibitors. Two potential residues, T63 and Y356, suitable for novel H-bonding interactions, were identified in the brequinar-binding pocket. Analogues were designed to maintain the essential pharmacophore and form new electrostatic interactions through strategically positioned H-bond accepting groups. This effort led to the discovery of potent quinoline-based analogues 41 (DHODH IC50 = 9.71 ± 1.4 nM) and 43 (DHODH IC50 = 26.2 ± 1.8 nM). A cocrystal structure between 43 and DHODH depicts a novel water mediated H-bond interaction with T63. Additional optimization led to the 1,7-naphthyridine 46 (DHODH IC50 = 28.3 ± 3.3 nM) that forms a novel H-bond with Y356. Importantly, compound 41 possesses significant oral bioavailability (F = 56%) and an elimination t1/2 = 2.78 h (PO dosing). In conclusion, the data supports further preclinical studies of our lead compounds toward selection of a candidate for early-stage clinical development.

COMPOUNDS FOR TREATMENT OF GLIOBLASTOMA

The present invention relates to compounds and methods for the treatment of glioblastoma, as well as to a pharmaceutical composition comprising said compounds. More specifically the invention relates to substituted quinoline derivatives having the formula (I), (II) or (III), and a pharmaceutical composition comprising said compounds for the treatment of cancer. (Formulae (I), (II), (III))

Energy efficient Pfitzinger reaction: A novel strategy using a surfactant catalyst

A novel energy efficient method for the Pfitzinger reaction is demonstrated, which is catalysed using a surfactant, cetyltrimethylammonium hydroxide. The surfactant nature of the catalyst caused the substrate to be soluble in aqueous media, which enhanced the interaction of the catalyst with the substrate. An increase in the rate of reaction and more than 78% of energy saving were observed under ultrasonic irradiation.

Hypoboric acid derivative based on 2-(4-dyhydroxy borane)pheoylquinoline-4-carboxylic acid and preparation method and application thereof

The invention discloses a hypoboric acid derivative based on 2-(4-dyhydroxy borane)pheoylquinoline-4-carboxylic acid and a preparation method thereof. The hypoboric acid derivative is used for preparing catecholamine and carbohydrate fluorescent probes. T