5777-20-8

Basic information

• Product Name: 3-hydroxy-isoxazole
• Synonyms: 3-hydroxy-isoxazole;3(2H)-Isoxazolone;3-Isoxazolol;Isoxazol-3-ol;Isoxazol-3-one;1,2-oxazol-3-ol
• CAS NO: 5777-20-8
• Molecular Formula: C₃H₃NO₂
• Molecular Weight: 85
• Product Categories: Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5777-20-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 98-99℃
• Boiling Point: 221.5 °C at 760 mmHg
• Flash Point: 87.7 °C
• Appearance: /
• Density: 1.296
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly)
• PKA: 12.56±0.20(Predicted)
• CAS DataBase Reference: 3-hydroxy-isoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-isoxazole(5777-20-8)
• EPA Substance Registry System: 3-hydroxy-isoxazole(5777-20-8)

Safety Data

• Hazardous Substances Data: 5777-20-8(Hazardous Substances Data)

Usage

Uses

3(2H)-Isoxazolone is a 3-hydroxyisoxazole with fungicidal activity. 3(2H)-Isoxazolone is an impurity of Cycloserine (C988800).

Upstream product

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

Downstream Products

• 73028-20-3 2-benzyl-isoxazol-3-one 
• 252328-83-9 MMV₆₈₇₈₁₃ 
• 252260-28-9 5(R)-Isoxazol-3-yloxymethyl-3-(4-methylsulfonylphenyl)oxazolidin-2-one 
• 252330-16-8 5(R)-Isoxazol-3-yloxymethyl-3-(4-iodophenyl)oxazolidin-2-one 
• 252280-14-1 3-(3-Fluoro-4-(imidazol-1-yl)phenyl)-5(R)-(isoxazol-3-yloxymethyl)-oxazolidin-2-one 
• 252280-03-8 3-(4-(1,4-Dioxa-8-azaspiro[4,5]decan-8-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one 
• 252328-94-2 5(R)-Isoxazol-3-yloxymethyl-3-(4-(1-benzyl-1,2,5,6-tetrahydropyrid-4-yl)-3-fluorophenyl)oxazolidin-2-one 
• 252260-22-3 5(R)-Isoxazol-3-yloxymethyl-3-(4-morpholino-3-fluoro-phenyl)oxazolidin-2-one 
• 252336-81-5 3-(4-((3R)-3-t-Butoxycarbonylamino-1-pyrrolidinyl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxy-methyl)oxazolidin-2-one 
• 882185-19-5 tert-butyl 4-(2-fluoro-4-{(5R)-5-[(isoxazol-3-yloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}phenoxy)piperidine-1-carboxylate 
• 53706-42-6 3-oxo-3H-isoxazole-2-carboxylic acid 4-chloro-N-propyl-anilide 
• 343784-75-8 (5RS)-3-(4-Bromophenyl)-5-isoxazol-3-yloxymethyl-4,5-dihydro-isoxazole 
• 1401342-89-9 (R)-3-(4-bromo-3-fluorophenyl)-5-((isoxazol-3-yloxy)methyl)oxazolidin-2-one 
• 1574506-93-6 3-benzyloxyisoxazole 

Relevant articles and documents

KETONE INHIBITORS OF LYSINE GINGIPAIN

The present invention provides compounds according to Formula (I) as described herein, and their use for inhibiting the lysine gingipain protease (Kgp) from the bacterium Porphyromonas gingivalis. Also described are gingipain activity probe compounds and methods for assaying gingipain activity are also described, as well as methods for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease.

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.