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

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

Used in Pharmaceutical Industry:
3-Hydroxy-isoxazole is used as an impurity in the production of Cycloserine (C988800), an antibiotic used for the treatment of tuberculosis. Its presence, although as an impurity, contributes to the overall effectiveness of the drug in combating bacterial infections.
Used in Agricultural Industry:
3-Hydroxy-isoxazole is used as a fungicide for the protection of crops against various fungal infections. Its fungicidal activity helps in reducing the spread of diseases and ensures a healthy growth of plants, leading to increased agricultural productivity.
Used in Chemical Research:
3-Hydroxy-isoxazole serves as a valuable compound in the field of chemical research and development. Its unique structure and properties make it a potential candidate for the synthesis of new drugs and other chemical products with diverse applications.

Upstream product

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

Downstream Products

• 73028-20-3 2-benzyl-isoxazol-3-one 
• 129170-94-1 3-((R)-1-Octadecyloxymethyl-2-trityloxy-ethoxy)-isoxazole 
• 115406-35-4 3-((S)-1-Hexadecyloxymethyl-2-trityloxy-ethoxy)-isoxazole 
• 115406-33-2 1-O-hexadecyl-2-O-(3-isoxazolyl)-3-O-triphenylmethyl-sn-glycerol 
• 129170-95-2 3-((S)-1-Octadecyloxymethyl-2-trityloxy-ethoxy)-isoxazole 
• 887275-40-3 4-{2,6-difluoro-4-[(5R)-5-(isoxazol-3-yloxymethyl)-2-oxo-oxazolidin-3-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester 
• 344459-61-6 3-[4-(5,7-dihydro-pyrrolo[3,4-b]pyridin-6-yl)-3-fluoro-phenyl]-5-(isoxazol-3-yloxymethyl)-oxazolidin-2-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 

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.

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.

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.

NOVEL ANTIBACTERIAL COMPOUNDS

The invention relates to novel chimeric antibiotics of formula (I) Wherein R1 is CH2NHCOR5, heteroarylmethyl, heteroaryloxymethyl or heteroarylaminomethyl; R2 is H, OH, OSO3H, OPO3H2, OCH2OPO3H2, OCOCH2CH2COOH, OCOR6; R3 is H or halogen; R4 is (C1-C3)alkyl, (C1-C3)haloalkyl or cycloalkyl; R5 is alkyl or haloalkyl; and R6 is the residue of a naturally occurring amino acid or of dimethylaminoglycine. These chimeric compounds are useful in the manufacture of medicaments for the treatment of infections (e.g. bacterial infections).

Imidazolo-5-YL-2anilino-pyrimidines as agents for the inhibition of the cell proliffration

Compounds of the formula (I): wherein R1, R2, R3, R4, R5, R6, p, q, and n are as defined within and a pharmaceutically acceptable salts and in vivo hydrolysable esters are described. Also described are processes for their preparation and their use as medicaments, particularly medicaments for producing a cell cycle inhibitory (anti-cell-proliferation) effect in a warm-blooded animal, such as man.

NOVEL FLORFENICOL-TYPE ANTIBIOTICS

The present invention relates to novel florfenicol compounds having the chemical structure: wherein the compounds are useful for the treatment and/or prevention of bacterial infections in a broad range of patients such as, without limitation, birds, fish, shellfish and mammals

Antimicrobial thiadiazinone derivatives and their application for treatment of bacterial infections

The present invention provides certain thiadiazinone derivatives of oxazolidinones of the following formula I: or pharmaceutically acceptable salts thereof that are antibacterial agents, pharmaceutical compositions containing them, methods for their use,

Isoxazolone compounds useful in treating diseases associated with unwanted cytokine activity

Isoxazolone compounds having the generic structure: are used to treat disease associated with unwanted cytokine activity, including rheumatoid arthritis, osteoarthritis, diabetes, HIV/AIDS, inflammatory bowel disease, Crohn's disease, ulcerative colitis,