76253-77-5

Upstream product

• 613-30-9 2-methyl-6-nitroquinoline 
• 76253-89-9 2-methyl-6-nitroquinoline N-oxide 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 137898-55-6 N-methyl-6-nitro-N-<(4-nitrophenoxy)propyl>-2-quinolinemethanamine 
• 137898-56-7 N-cyclopentyl-6-nitro-N-<(4-nitrophenoxy)propyl>-2-quinolinemethanamine 
• 137898-76-1 2-({[3-(4-Amino-phenoxy)-propyl]-methyl-amino}-methyl)-quinolin-6-ylamine 
• 137898-77-2 2-({[3-(4-Amino-phenoxy)-propyl]-cyclopentyl-amino}-methyl)-quinolin-6-ylamine 
• 141770-88-9 N-[4-[3-[[(6-Amino-2-quinolinyl)methyl]methylamino]-2-hydroxypropoxy] phenyl]methanesulfonamide 
• 141770-87-8 N-[4-[2-Hydroxy-3-[methyl[(6-nitro-2-quinolinyl)methyl]amino]propoxy]phenyl]methanesulfonamide 
• 139047-48-6 N-<2-<phenoxy>propyl>amino>methyl>-6-quinolinyl>methanesulfonamide 
• 141770-89-0 N-<2-<<<2-hydroxy-3-<4-<(methylsulfonyl)amino>phenoxy>propyl>methylamino>methyl>-6-quinolinyl>methanesulfonamide 
• 119198-19-5 N-Ethyl-N-(6-nitroquinol-2-ylmethyl)-4-methanesulphonamidophenethylamine 

Relevant academic research and scientific papers

Copper(II) catalyzed heterobenzylic C(sp3)-H activation: Two efficient halogenation methodologies towards heterobenzyl halides

Two practical and simple synthetic methodologies towards various heterobenzyl halides were developed. A series of 2-halomethylquinolines were readily prepared by the one-pot reaction of 2-methylquinolines with CuX (X = I, Br, Cl) and TBHP in CH3CN. A large variety of heterobenzyl iodides, including 2-iodomethylquinolines, 2-iodomethylquinoxalines, 2-iodiomethylbenzooxazole, and 2-iodiomethylbenzothiazole, were efficiently synthesized by one-pot reaction of 2-methylheterocycles with iodine in the presence of CuSO4·5H2O in CH3CN.

Microwave-assisted α-halogenation of 2-methylquinolines with tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane)

A simple and efficient methodology permitting the halogenation of 2-methylquinolines into 2-(chloromethyl)quinolines or 2-(bromomethyl)quinolines in the tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane) system has been developed for the first time. The halogenation can be rapidly completed with good to excellent yields and high selectivity under microwave irradiation.

N-quinolinyl alkyl-substituted 1-aryloxy-2-propanolamine and propylamine derivatives possessing class III antiarrhythmic activity

This invention relates to N-heteroalkyl-substituted 1-aryloxy-2-propanolamine and propylamine derivatives possessing anti-arrhythmic activity, to pharmaceutical compositions and to methods for production thereof.

Synthesis and Selective Class III Antiarrhythmic Activity of Novel N-Heteroaralkyl-Substituted 1-(Aryloxy)-2-propanolamine and Related Propylamine Derivatives

The synthesis and biological evaluation of a series of novel 1-(aryloxy)-2-propanolamines and several related deshydroxy analogues are described.Compounds 4-29 were prepared and investigated for their class III electrophysiological activity in isolated canine Purkinje fibers and in anesthetized open-chest dogs.None of these compounds showed any class I activity.On the basis of the in vitro data, structure-activity relationships for the series are discussed.Two compounds, N-propoxy>phenyl>methanesulfonamide (12, WAY-123,223) and N-phenoxy>propyl>amino>methyl>-6-quinolinyl>methanesulfonamide (24, WAY-125,971) were identified and characterized as potent and specific class III antiarrhythmic agents in vitro and in vivo.Compound 12 was found to be orally bioavailable, to produce large increases of ventricular fibrillation threshold (VFT), and, in some instances, to restore sinus rhythm from ventricular fibrillation in anesthetized open-chest dogs at a dose of 5 mg/kg (iv).The enantiomers of 12 (i.e., 13 and 14) were synthesized and were found to exhibit similar electrophysiological effects in the Purkinje fiber screen.Compound 24, a propylamine analogue with potency and efficacy comparable to those of UK-68798 (2) and E-4031 (3), was studied in voltage-clamp experiments (isolated cat myocytes) and was found to be a potent and specific blocker of the delayed rectifier potassium current (IK).

STUDIES ON TERTIARY AMINE OXIDES. LXIX. REACTIONS OF 2-CHLOROMETHYLQUINOLINE DERIVATIVES WITH 2-NITROPROPANE

Reactions of 2-chloromethylquinoline (1), its N-oxide (2) and their nitro derivatives with the sodium salt of 2-nitropropane were investigated.O-Alkylation occured with 1 and 2, giving 2-quinolinecarboxaldehyde (5: 11 percent) and its N-oxide (6: 10 percent).The reaction of 2-chloromethyl-5-nitroquinoline (3b) gave both the O-alkylation product, 5-nitro-2-quinolinecarboxyaldehyde (7: 21 percent), and the C-alkylation products, 2-(2-methyl-2-nitropropyl)-5-nitroquinoline (8b: 24 percent) and 2-(2-methyl-1-propenyl)-5-nitroquinoline (9b: trace).In the reactions of the 6-nitro (3c) and 8-nitro (3d) derivatives of 1, the 2-(2-methyl-2-nitropropyl)quinolines (8c: 86percent and 8d: 63 percent) were predominantly formed.In contrast, the reactions of the 4-nitro (4a), 5-nitro (4b) and 6-nitro (4c) derivatives of 2 produced the corresponding 2-(2-methyl-1-propenyl)quinoline N-oxides (11a: 53 percent, 11b: 20 percent and 11c: 66 percent) as main products, accompanied by small amounts of the 2-(2-methyl-2-nitropropyl) compounds (10a: 20 percent and 10b: 17 percent).Keywords-nucleophilic substitution; radical anion-free radical chain process; SRN1 mechanism; C-alkylation; O-alkylation; nitro derivatives of 2-chloromethylquinoline; nitro derivatives of 2-chloromethylquinoline 1-oxide; 2-(2-methyl-2-nitropropyl)quinolines and their N-oxides; 2-(2-methyl-1-propenyl)quinolines and their N-oxides