127925-01-3

Basic information

• Product Name: 3-Isoxazolol
• CAS NO: 127925-01-3
• Molecular Formula: C3H3NO2
• Molecular Weight: 85.06142
• Mol File: 127925-01-3.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Isoxazolol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Isoxazolol(127925-01-3)
• EPA Substance Registry System: 3-Isoxazolol(127925-01-3)

Safety Data

• Hazardous Substances Data: 127925-01-3(Hazardous Substances Data)

Usage

Properties

1. Molecular Formula: C3H3NO
2. Chemical Structure: A five-membered heterocyclic ring composed of three carbon atoms, one nitrogen atom, and one oxygen atom.
3. Classification: Isoxazolol derivative, belonging to the isoxazole family.
4. Reactivity: Highly reactive and versatile.
5. Utility: Widely used as a building block for synthesizing various pharmaceuticals and agrochemicals.
6. Industrial Use: Serves as a starting material for the production of other organic compounds, such as insecticides and herbicides.
7. Biological Activity: Exhibits biological activity, making it of interest for potential therapeutic applications.

Specific Content

1. Chemical Composition: Three carbon atoms, one nitrogen atom, and one oxygen atom.
2. Functional Group: Contains an isoxazolol ring, which imparts specific chemical properties.
3. Synthetic Applications: Used as a key intermediate in the synthesis of pharmaceuticals and agrochemicals.
4. Industrial Importance: Valued as a precursor for manufacturing various organic compounds, particularly in the agricultural sector.
5. Biomedical Research: Derivatives of 3-Isoxazolol are studied for potential therapeutic benefits, indicating its significance in drug discovery.
6. Versatility: Its high reactivity allows for diverse chemical transformations, enabling the creation of complex molecular structures.
7. Chemical Interactions: Can undergo various chemical reactions to form bonds with other compounds, facilitating the creation of novel substances.
8. Regulatory Considerations: Due to its role in the synthesis of pharmaceuticals, agrochemicals, and other industrial compounds, it may be subject to regulatory oversight and safety assessments.

This summary encapsulates the essential properties and applications of 3-Isoxazolol, highlighting its significance in both chemical synthesis and potential therapeutic development.

Upstream product

• 5470-11-1 hydroxylamine hydrochloride 
• 623-47-2 propynoic acid ethyl ester 
• 922-67-8 propynoic acid methyl ester 
• 141-52-6 sodium ethanolate 
• 127-07-1 N-hydroxyurea 

Downstream Products

• 115406-35-4 3-((S)-1-Hexadecyloxymethyl-2-trityloxy-ethoxy)-isoxazole 
• 129170-95-2 3-((S)-1-Octadecyloxymethyl-2-trityloxy-ethoxy)-isoxazole 
• 1401342-89-9 (R)-3-(4-bromo-3-fluorophenyl)-5-((isoxazol-3-yloxy)methyl)oxazolidin-2-one 
• 1574506-93-6 3-benzyloxyisoxazole 
• 73028-20-3 2-benzyl-isoxazol-3-one 

Relevant articles and documents

Development of a safe, scalable process for the preparation of an oxaisoxazolidinone

This report describes the development and scale up of the synthesis of oxaisoxazolidinone 1, a significant synthon in the synthesis of the MRSA development compound AZD5847. Studies were carried out to ensure a short-term, risk based preparation of 9 on a 5 L scale with a solid isolation procedure and a safe, long-term manufacturing process for both 1 and 9 through extensive hazards evaluation.

NOVEL OXAZOLIDINONE DERIVATIVE AND MEDICAL COMPOSITION CONTAINING SAME

Disclosed is a novel oxazolidinone derivative represented by Formula 1 above, in particular, a novel oxazolidinone compound having a cyclic amidoxime or cyclic amidrazone group. In Formula 1, R and Q are the same as defined in the detailed description. In addition, disclosed is a pharmaceutical composition for an antibiotic which includes the novel oxazolidinone derivative of Formula 1, a prodrug thereof, a hydrate thereof, a solvate thereof, an isomer thereof, or a pharmaceutically acceptable salt thereof as an active ingredient. The novel oxazolidinone derivative, the prodrug thereof, the hydrate thereof, the solvate thereof, the isomer thereof, and the pharmaceutically acceptable salt thereof have broad antibacterial spectrum against resistant bacteria, low toxicity and strong antibacterial effects against Gram-positive and Gram-negative bacteria and thus may be effectively used as antibiotics.

Discovery of torezolid as a novel 5-hydroxymethyl-oxazolidinone antibacterial agent

A series of novel substituted pyridyl phenyl oxazolidinone analogues were synthesized and their structure-activity relationship (SAR) was investigated based on in vitro and in vivo antibacterial activities. The minimum inhibitory concentrations (MICs) of the synthesized compounds against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) ranged from 0.12 to 2.0 μg/mL, and against Haemophilus influenzae (Hi) from 2.0 to 8.0 μg/mL. Compared to linezolid, only four compounds (11, 12, 21 and 29) showed higher in vitro antibacterial activities and better in vivo protective effects in mice. To improve the aqueous solubility, various prodrugs of compound 11 (DA-7157), which exerted a potency that was enhanced by 2-8-fold compared to that of linezolid, were synthesized. Among the prodrugs, the phosphate compound 42 exhibited excellent aqueous solubility (>50 mg/mL in DW) and good pharmacokinetic profiles, along with better in vivo efficacy than linezolid. This compound 42 is currently undergoing clinical trials with the brand name Torezolid.