181048-49-7

Basic information

• Product Name: 2-(2-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID
• Synonyms: 2-(2-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID;4-Quinolinecarboxylic acid, 2-(2-Methoxyphenyl)-;2-(2-methoxyphenyl)cinchoninic acid
• CAS NO: 181048-49-7
• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279.29
• Mol File: 181048-49-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 218.6-222.0 °C(Solv: ethanol (64-17-5))
• Boiling Point: 451.8 °C at 760 mmHg
• Flash Point: 227 °C
• Appearance: /
• Density: 1.277 g/cm³
• Vapor Pressure: 5.99E-09mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 0.97±0.10(Predicted)
• CAS DataBase Reference: 2-(2-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID(181048-49-7)
• EPA Substance Registry System: 2-(2-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID(181048-49-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 181048-49-7(Hazardous Substances Data)

Usage

General Description

2-(2-Methoxy-phenyl)-quinoline-4-carboxylic acid is a chemical compound with a molecular formula C20H15NO3. It is a quinoline derivative that contains a carboxylic acid group and a methoxyphenyl group. 2-(2-METHOXY-PHENYL)-QUINOLINE-4-CARBOXYLIC ACID is commonly used in organic synthesis and medicinal chemistry research, as well as in the pharmaceutical industry. Its structure and properties make it a valuable building block for the development of various drugs and bioactive molecules. Additionally, it has the potential to exhibit a wide range of biological activities, including anti-inflammatory and antioxidant properties.

InChI:InChI=1/C17H13NO3/c1-21-16-9-5-3-7-12(16)15-10-13(17(19)20)11-6-2-4-8-14(11)18-15/h2-10H,1H3,(H,19,20)/p-1

Upstream product

• 579-74-8 2-Methoxyacetophenone 
• 91-56-5 indole-2,3-dione 
• 4079-52-1 methoxymethyl phenyl ketone 
• 127-17-3 2-oxo-propionic acid 
• 62-53-3 aniline 
• 135-02-4 ortho-anisaldehyde 

Downstream Products

• 181048-08-8 2-(2'-methoxyphenyl)quinoline-4-carbonylguanidine 
• 174636-72-7 2-(2-Methoxy-phenyl)-quinoline-4-carbonyl chloride 

Relevant articles and documents

Construction of acid-base bifunctional covalent organic frameworks: Via Doebner reaction for catalysing cascade reaction

We report herein a series of quinoline-4-carboxylic acid linked COFs via the multicomponent one-pot in situ Doebner reaction. The obtained acid-base bifunctional COFs are chemically stable and can highly promote one-pot cascade deacetalization-Knoevenagel condensation reaction in a heterogeneous way under solvent-free conditions. This journal is

Discovering novel chemical inhibitors of human cyclophilin A: Virtual screening, synthesis, and bioassay

Cyclophilin A (CypA) is a member of cyclophilins, a family of the highly homologous peptidyl prolyl cis-trans isomerases (PPIases), which can bind to cyclosporin A (CsA). CypA plays critical roles in various biological processes, including protein folding, assembly, transportation, regulation of neuron growth, and HIV replication. The discovery of CypA inhibitor is now of a great special interest in the treatment of immunological disorders. In this study, a series of novel small molecular CypA inhibitors have been discovered by using structure-based virtual screening in conjunction with chemical synthesis and bioassay. The SPECS_1 database containing 85,000 small molecular compounds was searched by virtual screening against the crystal structure of human CypA. After SPR-based binding affinity assay, 15 compounds were found to show binding affinities to CypA at submicro-molar or micro-molar level (compounds 1-15). Seven compounds were selected as the starting point for the further structure modification in considering binding activity, synthesis difficulty, and structure similarity. We thus synthesized 40 new small molecular compounds (1-6, 15, 16a-q, 17a-d, and 18a-l), and four of which (compounds 16b, 16h, 16k, and 18g) showed high CypA PPIase inhibition activities with IC50s of 2.5-6.2 μM. Pharmacological assay indicated that these four compounds demonstrated somewhat inhibition activities against the proliferation of spleen cells.

Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 1. Identification of the 4-quinolinecarboxamide framework

A novel class of potent and selective non-peptide neurokinin-3 (NK-3) receptor antagonists, featuring the 4-quinolinecarboxamide framework, has been designed based upon chemically diverse NK-1 receptor antagonists. The novel compounds 33-76, prompted by chemical modifications of the prototype 4, have been characterized by binding analysis using a membrane preparation of chinese hamster ovary (CHO) cells expressing the human neurokinin-3 receptors (hNK-3-CHO), and clear structure-activity relationships (SARs) have been established. From SARs, (R)-N-[α-(methoxycarbonyl)benzyl]-2- phenylquinoline-4-carboxamide (65, SB 218795, hNK-3-CHO binding K(i) = 13 nM) emerged as one of the most potent compounds of this novel class. Selectivity studies versus the other neurokinin receptors (hNK-2-CHO and hNK-1-CHO) revealed that 65 is about 90-fold selective for hNK-3 versus hNK-2 receptors (hNK-2-CHO binding K(i) = 1221 nM) and over 7000-fold selective versus hNK-1 receptors (hNK-1-CHO binding K(i) = >100 μM). In vitro functional studies in rabbit isolated iris sphincter muscle preparation demonstrated that 65 is a competitive antagonist of the contractile response induced by the potent and selective NK-3 receptor agonist senktide with a K(b) = 43 nM. Overall, the data indicate that 65 is a potent and selective hNK-3 receptor antagonist and a useful lead for further chemical optimization.