948893-91-2

Basic information

• Product Name: (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one
• Synonyms: (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one
• CAS NO: 948893-91-2
• Molecular Weight: 450.613
• EINECS: -0
• Mol File: 948893-91-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one(948893-91-2)
• EPA Substance Registry System: (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one(948893-91-2)

Safety Data

• Hazardous Substances Data: 948893-91-2(Hazardous Substances Data)

Usage

Description

(R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one is a chiral quinolin-2(1H)-one derivative featuring an azido group, a tert-butyldimethylsilyl group, and a benzyloxy moiety. (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one is characterized by its (R) configuration at the 5-position and is known for its potential biological activities, such as antiviral, antibacterial, and anticancer properties. The presence of the azido and benzyloxy groups suggests its utility in medicinal chemistry and drug development, while the tert-butyldimethylsilyl group serves as a protective group in organic synthesis, enabling selective reactions at other functional groups within the molecule.

Uses

Used in Pharmaceutical Industry:
(R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one is used as a potential therapeutic agent for various diseases due to its diverse biological activities, including antiviral, antibacterial, and anticancer properties. (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one's unique structure allows for further modification and optimization to enhance its pharmacological effects and selectivity.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one serves as a valuable starting material for the development of new drugs. Its azido and benzyloxy groups can be exploited for the synthesis of various bioactive molecules, while the tert-butyldimethylsilyl group provides a handle for selective functionalization and protection of the molecule during synthesis.
Used in Drug Development:
(R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one is used as a lead compound in drug development. Its chiral nature and the presence of multiple functional groups make it an attractive candidate for the design and synthesis of novel therapeutic agents. (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one's structure can be further modified to improve its pharmacokinetic and pharmacodynamic properties, potentially leading to more effective treatments for various diseases.
Used in Organic Synthesis:
In the realm of organic synthesis, (R)-5-(2-azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one is used as a versatile building block for the construction of complex molecular architectures. The tert-butyldimethylsilyl group serves as a protective group, allowing for selective reactions at other functional groups within the molecule, while the azido and benzyloxy groups can be employed in various synthetic transformations to access a wide range of chemical products.

Upstream product

• 530084-79-8 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 100331-89-3 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one 
• 93609-84-8 5-acetyl-8-benzyloxy-1H-quinolin-2-one 
• 530084-74-3 (R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one 

Downstream Products

• 1415970-74-9 (1-(9-((2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)nonyl)piperidin-4-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate 
• 1613593-47-7 2-(4-((((R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)methyl)-2-methylphenoxy)ethyl 4-((3-((S)-phenyl((((R)-quinuclidin-3-yloxy)carbonyl)amino)methyl)phenoxy)methyl)benzoate 
• 948895-60-1 5-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(1-{2-[2-(2,6-dichlorophenyl)ethoxy]ethyl}-4-hydroxypiperidin-4-yl)methyl]amino}ethyl)-8-hydroxyquinolin-2(1H)-one 
• 948895-79-2 5-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(1-{2-[2-(2,3-dichlorophenyl)ethoxy]ethyl}-4-hydroxypiperidin-4-yl)methyl]amino}ethyl)-8-hydroxyquinolin-2(1H)-one 
• 948894-97-1 5-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(1-{2-[2-(3-chlorophenyl)ethoxy]ethyl}-4-hydroxypiperidin-4-yl)methyl]amino}ethyl)-8-hydroxyquinolin-2(1H)-one 
• 948895-30-5 5-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-{[(1-{2-[2-(2-chlorophenyl)ethoxy]ethyl}-4-hydroxypiperidin-4-yl)methyl]amino}ethyl)-8-hydroxyquinolin-2(1H)-one 
• 948893-93-4 5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[({4-hydroxy-1-[2-(2-phenylethoxy)ethyl]piperidin-4-yl}methyl)amino]ethyl}-8-hydroxyquinolin-2(1H)-one 
• 948894-20-0 5-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-[({(3R)-1-[2-(2-phenylethoxy)ethyl]piperidin-3-yl}methyl)amino]ethyl}-8-hydroxyquinolin-2(1H)-one 
• 948893-97-8 N-benzyl-3-(4-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}piperidin-1-yl)propanamide 
• 948896-05-7 N-[2-(4-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}piperidin-1-yl)ethyl]benzenesulfonamide 
• 948893-89-8 5-[(R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({1-[2-(2-phenylethoxy)ethyl]piperidin-4-yl}amino)ethyl]-8-hydroxyquinolin-2(1H)-one 
• 948894-99-3 benzyl (4-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}piperidin-1-yl)acetate 

Relevant articles and documents

Discovery of a novel class of inhaled dual pharmacology muscarinic antagonist and β2 agonist (MABA) for the treatment of chronic obstructive pulmonary disease (COPD)

The targeting of both the muscarinic and β-adrenergic pathways is a well validated therapeutic approach for the treatment of chronic obstructive pulmonary disease (COPD). In this communication we report our effort to incorporate two pharmacologies into a single chemical entity, whose characteristic must be suitable for a once daily inhaled administration. Contextually, we aimed at a locally acting therapy with limited systemic absorption to minimize side effects. Our lung-tailored design of bifunctional compounds that combine the muscarinic and β-adrenergic pharmacologies by the elaboration of the muscarinic inhibitor 7, successfully led to the potent, pharmacologically balanced muscarinic antagonist and β2 agonist (MABA) 13.

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY

Compounds of formula I, defined herein, act both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists and are useful for treating broncho-obstructive and inflammatory diseases.

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY

Compounds of formula (I) described herein act both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists and are useful for the prevention and/or treatment of broncho-obstructive or inflammatory diseases.