87864-14-0

Usage

Chemical Properties

Off-White Solid

Uses

Intermediate in the preparation of Dibucaine.

InChI:InChI=1/C16H20ClN3O/c1-3-20(4-2)10-9-18-16(21)13-11-15(17)19-14-8-6-5-7-12(13)14/h5-8,11H,3-4,9-10H2,1-2H3,(H,18,21)

Upstream product

• 2388-32-1 2-chloroquinoline-4-carbonyl chloride 
• 100-36-7 N,N-diethylethylenediamine 
• 15733-89-8 2-hydroxyquinoline-4-carboxylic acid 
• 5467-57-2 2-chloroquinoline-4-carboxylic acid 

Downstream Products

• 2717-03-5 N-(2-(diethylamino)ethyl)-2-(hexyloxy)quinoline-4-carboxamide 
• 2716-99-6 N-[2-(diethylamino)ethyl]-2-ethoxyquinoline-4-carboxamide 
• 112248-26-7 N-[2-(diethylamino)ethyl]-2-(2-ethoxyethoxy)quinoline-4-carboxamide 
• 109472-30-2 2-(2-methoxy-ethoxy)-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) 
• 85-79-0 Dibucaine 

Relevant academic research and scientific papers

SMALL MOLECULE ENTEROVIRUS INHIBITORS AND USES THEREOF

This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a quinoline (or similar) structure which function as antagonists of androgen receptor activity, and their use as therapeutics for the treatment of cancer (e.g., castration-resistant prostate cancer) and other conditions characterized with androgen receptor activity and/or androgen receptor expression.

Identification of dibucaine derivatives as novel potent enterovirus 2C helicase inhibitors: In vitro, in vivo, and combination therapy study

Enterovirus A71 (EV-A71) is a human pathogen causing hand, foot and mouth disease (HFMD) which seriously threatened the safety and lives of infants and young children. However, there are no licensed direct antiviral agents to cure the HFMD. In this study, a series of quinoline formamide analogues as effective enterovirus inhibitors were developed, subsequent systematic structure-activity relationship (SAR) studies demonstrated that these quinoline formamide analogues exhibited good potency to treat EV-A71 infection. As described, the most efficient EV-A71 inhibitor 6i showed good anti-EV-A71 activity (EC50 = 1.238 μM) in RD cells. Furthermore, compound 6i could effectively prevent death of virus infected mice at dose of 6 mg/kg. When combined with emetine (0.1 mg/kg), this treatment could completely prevent the clinical symptoms and death of virus infected mice. Mechanism study indicated that compound 6i inhibited EV-A71 via targeting 2C helicase, thus impeding RNA remodeling and metabolism. Taken together, these data indicated that 6i is a promising EV-A71 inhibitor and worth extensive preclinical investigation as a lead compound.

Quinoline formamide compound and preparation method thereof and application of anti-enterovirus type 71

The invention discloses a quinoline formamide compound and a preparation method thereof and an application of an anti-enterovirus type 71 (EV71), and belongs to the technical field of medicine. Specifically, 2-chloroquinoline-4-formamide derivative and an alcohol compound are subjected to a substitution reaction, so that a series of quinoline formamide compounds are prepared. The quinoline formamide compounds have the activity of resisting enterovirus type 71, have small toxicity to cells, can be developed as a new anti-EV 71 drug, and have a wide application prospect.

Method for preparing N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide

The invention discloses a method for preparing a dibucaine hydrochloride intermediate N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide by a one-pot method. The method comprises the followingsteps: using 2-hydroxy-4-carboxyquinoline and thionyl chloride to synthesize 2-chloroquinoline-4-formyl chloride under catalysis of DMF; concentrating a reaction liquid to dry; and directly reacting the product with N,N'-diethylethylenediamine under conditions of an acid binding agent to obtain N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide having a liquid phase purity of 99.9% or aboveand a yield of 93% or above. The method for preparing N-(2-(diethyl)aminoethyl)-2-chloro-4-quinolinecarboxamide has advantages of short production cycle, simple operation, low cost, high yield and high quality, and is conducive to industrial production.

Discovery of Quinoline Analogues as Potent Antivirals against Enterovirus D68 (EV-D68)

Enterovirus D68 (EV-D68) is an atypical nonpolio enterovirus that mainly infects the respiratory system of humans, leading to moderate-to-severe respiratory diseases. In rare cases, EV-D68 can spread to the central nervous system and cause paralysis in infected patients, especially young children and immunocompromised individuals. There is currently no approved vaccine or antiviral available for the prevention and treatment of EV-D68. In this study, we aimed to improve the antiviral potency and selectivity of a previously reported EV-D68 inhibitor, dibucaine, through structure-activity relationship studies. In total, 60 compounds were synthesized and tested against EV-D68 using the viral cytopathic effect assay. Three compounds 10a, 12a, and 12c were identified to have significantly improved potency (EC50 180) compared with dibucaine against five different strains of EV-D68 viruses. These compounds also showed potent antiviral activity in neuronal cells, such as A172 and SH-SY5Y cells, suggesting they might be further developed for the treatment of both respiratory infection as well as neuronal infection.