615568-38-2

Basic information

• Product Name: 6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one
• Synonyms: 6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one;6-(hydroxyMethyl)-2H,3H,4H-pyrido[3,2-b][1,4]oxazin-3-one;(6-HYDROXYMETHYL)-2H-PYRIDON[3,2-B]-1,4-OXAZIN-3(4H)-ONE;2-b][1;6-(hydroxyMethyl)-2H-pyrido[3
• CAS NO: 615568-38-2
• Molecular Formula: C8H8N2O3
• Molecular Weight: 180.16072
• Mol File: 615568-38-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 455.176°C at 760 mmHg
• Flash Point: 229.082°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: 6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one(615568-38-2)
• EPA Substance Registry System: 6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one(615568-38-2)

Safety Data

• Hazardous Substances Data: 615568-38-2(Hazardous Substances Data)

Usage

General Description

6-(Hydroxymethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one is a chemical compound that belongs to the class of heterocyclic compounds. It is a derivative of oxazole, a five-membered aromatic ring with one oxygen and one nitrogen heteroatom. The presence of a hydroxymethyl group in the structure suggests that it contains a hydroxyl group attached to a methylene group, which can act as a potential site for reactions with other molecules. The compound's molecular structure and properties make it of potential interest in medicinal chemistry and drug design for its potential biological activities and therapeutic applications. It may also have relevance in the field of organic chemistry for its potential use in the synthesis of other related compounds.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.