615568-38-2

Usage

Uses

Used in Medicinal Chemistry:
6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one is utilized as a compound of interest in medicinal chemistry for its potential to contribute to the development of new drugs. Its unique structure allows for exploration in various therapeutic areas, including the treatment of diseases and disorders where novel agents are needed.
Used in Drug Design:
In drug design, 6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one serves as a building block for the creation of new pharmaceutical agents. Its properties may enable the design of drugs with specific biological activities, targeting various medical conditions.
Used in Organic Chemistry:
6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one is also used in organic chemistry as an intermediate in the synthesis of other related compounds. Its reactivity and functional groups make it a valuable component in the preparation of complex organic molecules with diverse applications.

InChI:InChI=1/C8H8N2O3/c11-3-5-1-2-6-8(9-5)10-7(12)4-13-6/h1-2,11H,3-4H2,(H,9,10,12)

Upstream product

• 443956-11-4 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde 
• 15128-82-2 3-hydroxy-2-nitropyridine 
• 443956-08-9 6-bromo-2-nitropyridin-3-ol 
• 443956-09-0 ethyl 2-(6-bromo-2-nitropyridin-3-yloxy)acetate 
• 337463-88-4 6-bromo-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one 
• 911485-89-7 C₁₅H₁₂N₂O₂ 

Downstream Products

• 443956-11-4 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde 

Relevant academic research and scientific papers

Structure activity relationship of pyridoxazinone substituted RHS analogs of oxabicyclooctane-linked 1,5-naphthyridinyl novel bacterial topoisomerase inhibitors as broad-spectrum antibacterial agents (Part-6)

Abstract Oxabicyclooctane linked 1,5-naphthyridinyl-pyridoxazinones are novel broad-spectrum bacterial topoisomerase inhibitors (NBTIs) targeting bacterial DNA gyrase and topoisomerase IV at a site different than quinolones. Due to lack of cross-resistance to known antibiotics they present excellent opportunity to combat drug-resistant bacteria. A structure activity relationship of the pyridoxazinone moiety is described in this Letter. Chemical synthesis and activities of NBTIs with substitutions at C-3, C-4 and C-7 of the pyridoxazinone moiety with halogens, alkyl groups and methoxy group has been described. In addition, substitutions of the linker NH proton and its transformation into amide analogs of AM-8085 and AM-8191 have been reported. Fluoro, chloro, and methyl groups at C-3 of the pyridoxazinone moiety retained the potency and spectrum. In addition, a C-3 fluoro analog showed 4-fold better oral efficacy (ED50 3.9 mg/kg) as compared to the parent AM-8085 in a murine bacteremia model of infection of Staphylococcus aureus. Even modest polarity (e.g., methoxy) is not tolerated at C-3 of the pyridoxazinone unit. The basicity and NH group of the linker is important for the activity when CH2 is at the linker position-8. However, amides (with linker position-8 ketone) with a position-7 NH or N-methyl group retained potency and spectrum suggesting that neither basicity nor hydrogen-donor properties of the linker amide NH is essential for the activity. This would suggest likely an altered binding mode of the linker position-7,8 amide containing compounds. The amides showed highly improved hERG (functional IC50 >30 μM) profile.

BRIDGED BICYCLIC COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS

Novel bridged bicyclic compounds are disclosed herein, along with their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and methods of using such compounds as antibacterial agents. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating bacterial infections and associated diseases and conditions.

NITROGEN-CONTAINING BICYCLIC HETEROCYCLES FOR USE AS ANTIBACTERIALS

Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives hereof useful in methods of treatment of bacterial infections in mammals, particularly man.