30696-07-2

Usage

Synthesis

N-phenylquinolin-4-amine was prepared by adding aniline to 4-chloroquinoline ethanol solution under microwave irradiation at 165°C.Experiment steps：To a solution of 4-chloroquinoline (350 mg, 2.14 mmol) in ethanol (3 ml), aniline (996 mg, 10.7 mmol) was added and the mixture was reacted at 165 °C for 3 hours under microwave radiation. The reaction mixture was concentrated in vacuo, aqueous sodium carbonate (25 ml) was added and this was then extracted using dichloromethane (3×30 ml). The organic extracts were collected, dried using magnesium sulphate, concentrated in vacuo and the resulting residue was purified by flash column chromatography eluting with 2% methanol in dichloromethane to give N-phenylquinolin-4-amine as a colourless solid (42 mg, 9%).

Upstream product

• 611-35-8 4-chloroquinoline 
• 62-53-3 aniline 
• 824935-59-3 4-anilino-2-chloroquinoline 
• 50634-27-0 1,4-dithiino[2,3-c:5,6-c']diquinoline 
• 142-04-1 aniline hydrochloride 
• 3964-04-3 4-bromoquinoline 
• 6628-93-9 4-anilino-quinolin-2-ol 
• 1035458-54-8 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)quinoline 
• 65148-06-3 N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine 
• 205985-49-5 4-chloro-3-quinolinesulfonic acid 
• 157494-40-1 4-chloro-3-quinolinesulfonyl chloride 
• 611-36-9 quinolin-4-ol 
• 529-37-3 4(1H)-quinolinone 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 681828-29-5 N-phenyl-N-quinolin-4-yl-acetamide 
• 681828-44-4 N-phenyl-N-1,2,3,4-tetrahydroquinolin-4-ylacetamide 
• 681828-43-3 cis-N-Phenyl-N-[1-(thiophene-2-carbonyl)-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide 

Relevant academic research and scientific papers

Spectroscopic Studies of the Chan-Lam Amination: A Mechanism-Inspired Solution to Boronic Ester Reactivity

We report an investigation of the Chan-Lam amination reaction. A combination of spectroscopy, computational modeling, and crystallography has identified the structures of key intermediates and allowed a complete mechanistic description to be presented, including off-cycle inhibitory processes, the source of amine and organoboron reactivity issues, and the origin of competing oxidation/protodeboronation side reactions. Identification of key mechanistic events has allowed the development of a simple solution to these issues: manipulating Cu(I) → Cu(II) oxidation and exploiting three synergistic roles of boric acid has allowed the development of a general catalytic Chan-Lam amination, overcoming long-standing and unsolved amine and organoboron limitations of this valuable transformation.

Identification of 4-Phenoxyquinoline Based Inhibitors for L1196M Mutant of Anaplastic Lymphoma Kinase by Structure-Based Design

Dysregulation of anaplastic lymphoma kinase (ALK) has been detected in nonsmall cell lung cancer (NSCLC) in the form of EML4-ALK fusion. Secondary mutations opposing activity of the first-generation ALK inhibitor crizotinib came into existence, requiring mutation-targeting drug discovery for the powerful second-line treatment. In this study, we report 4-phenoxyquinoline-based inhibitors that overcome crizotinib resistance to ALK L1196M, discovered by the fragment-growing strategy. The protonation of 4-aminoquinoline core could interrupt the ability the N atom of quinoline to act as a hydrogen bond acceptor; therefore, the pKa and calculated ionization pH values of relevant pyridine-based core moieties were carefully analyzed. The replacement of amine linkage with ether resulted in single-digit nanomolar range inhibitors. The inhibitors exhibited significant antiproliferative effects on H2228 CR crizotinib-resistant cells by decreasing PI3K/AKT and MAPK signaling. This work constitutes the first example for systematic investigation of the effect of ionization pH on activity in this system.

Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists

Quinoline, isoquinoline, quinoxaline, and quinazoline derivatives were synthesized using microwave-assisted synthesis and their CB1/CB2 receptor activities were determined using the [35S]GTPγS binding assay. Most of the prepared quinoline, isoquinoline, and quinoxalinyl phenyl amines showed low-potency partial CB2 receptor agonists activity. The most potent CB2 ligand was the 4-morpholinylmethanone derivative (compound 40e) (-log EC 50 = 7.8; Emax = 75%). The isoquinolin-1-yl(3- trifluoromethyl-phenyl)amine (compound 26c) was a high efficacy CB2 agonist (-log EC50 = 5.8; Emax = 128%). No significant CB1 receptor activation or inactivation was shown in these studies, except 40e, which showed weak CB1 agonist activity (CB1 -log EC50 = 5.0). These ligands serve as novel templates for the development of selective CB2 receptor agonist.

Assembly of 4-aminoquinolines via palladium catalysis: A mild and convenient alternative to SNAr methodology

4-Aminoquinolines, classically prepared via SNAr chemistry from an amine and 4-haloquinoline, are important scaffolds in medicinal chemistry. Interest in these compounds prompted us to explore palladium catalysis as an alternative to the existing methods for their preparation. Initial results followed by an iterative screening paradigm confirmed Pd(OAc)2/ DPEphos/K3PO4 as a mild and convenient alternative for the formation of the C-N bond in 4-aminoquinolines. A description of the screen and the scope of this methodology are discussed herein.

Heteroatom directed photoannulation: synthesis of indoloquinoline alkaloids: cryptolepine, cryptotackieine, cryptosanguinolentine, and their methyl derivatives

A three-step synthesis of indoloquinoline alkaloids is described. The reaction of 2,3 and 4-substituted haloquinolines with anilines afforded the respective anilinoquinolines, which upon photocyclization gave the indoloquinolines. By regioselective methylation on quinoline nitrogen, furnished the alkaloids cryptotackieine, cryptosanguinolentine, cryptolepine, and the synthetic isomer isoneocryptolepine. Their methyl derivatives were also synthesized in search of new antiplasmodial drugs and DNA intercalating agents.

Symmetrical bis-quinolinium compounds: New human choline kinase inhibitors with antiproliferative activity against the HT-29 cell line

Studies have been aimed at the establishment of structure-activity relationships that define choline kinase inhibitory and antiproliferative activities of 40 bisquinolinium compounds. These derivatives have electron-releasing groups at position 4 of the q

Tetrahydroquinoline derivatives as CRTH2 antagonists

The invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the description, their use as medicament, pharmaceutical compositions containing them and processes for their preparation.

Quinoline derivatives as CRTH2 antagonists

The invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the description, their use as medicament, pharmaceutical compositions containing them and processes for their preparation.

Synthesis of 4-amino-3-quinolinesulfonic acids and 4-aminoquinolines

The hydrolysis of 4-chloro-3-quinolinesulfonyl chloride (1) gives 4-chloro-3-quinolinesulfonic acid (2) or 1,4-dihydro-4-oxo-3-quinolinesulfonic acid (3). Compound (2) reacts with primary and secondary aliphatic or primary aromatic amines to give 4-amino-