87864-14-0

Basic information

• Product Name: 2-Chloro-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide
• Synonyms: 2-Chloro-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide;4-Quinoline-carboxamide,2-Chloro-N-[2-(Diethylamino)Ethyl];N-(2-Diethylaminoethyl)-2-chloro-4-quinolinecarboxamide;2-Chloro-N-(2-diethylaMinoethyl)cinchoninaMide;Desbutoxy 2-Chloro Dibucaine;2-chloro-N-[2-(die1,2-dihydrothylaMino)ethyl]-4-quinolinecarboxaMide;2-Chloro-N-(2-(diethylaMino)ethyl)quinoline-4-carboxaMide;4-quinolinecarboxamide, 2-chloro-N-[2-(diethylamino
• CAS NO: 87864-14-0
• Molecular Formula: C₁₆H₂₀ClN₃O
• Molecular Weight: 305.8025
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 87864-14-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 65-67°C
• Boiling Point: 470.5°C at 760 mmHg
• Flash Point: 238.3°C
• Appearance: /
• Density: 1.181g/cm³
• Vapor Pressure: 5.05E-09mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 12.77±0.46(Predicted)
• CAS DataBase Reference: 2-Chloro-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide(87864-14-0)
• EPA Substance Registry System: 2-Chloro-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide(87864-14-0)

Safety Data

• Hazardous Substances Data: 87864-14-0(Hazardous Substances Data)

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

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.