178747-83-6

Basic information

• Product Name: 1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI)
• Synonyms: 1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI);4-Fluorobenzo[d]isoxazol-3(2H)-one;4-fluorobenzo[d]isoxazol-3-ol;4-Fluoro-1,2-benzisoxazol-3(2H)-one
• CAS NO: 178747-83-6
• Molecular Formula: C7H4FNO2
• Molecular Weight: 153.1105632
• Product Categories: HALIDE;OXAZOLE
• Mol File: 178747-83-6.mol

Chemical Properties

• Melting Point: 201-205℃
• Appearance: /
• Density: 1.440±0.06 g/cm3 (20℃ 760 Torr)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI)(178747-83-6)
• EPA Substance Registry System: 1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI)(178747-83-6)

Safety Data

• Hazardous Substances Data: 178747-83-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI) is utilized as a key intermediate in the synthesis of new drugs and pharmaceutical compounds. Its unique chemical structure and properties allow it to interact with biological targets, making it an interesting molecule for the development of novel therapeutic agents.
1,2-Benzisoxazol-3(2H)-one,4-fluoro-(9CI) is also used as a research tool in medicinal chemistry. Its specific interactions with biological targets provide valuable insights into the design and optimization of new drug candidates, contributing to the advancement of drug discovery and development processes.

Upstream product

• 125309-34-4 2,6-difluoro-N-hydroxybenzamide 
• 1034249-02-9 C₁₇H₁₆FNO₅ 
• 67531-86-6 6-fluorosalicylic acid 
• 72373-81-0 Methyl 2-fluoro-6-hydroxybenzoate 
• 855996-64-4 2-fluoro-N,6-dihydroxybenzamide 

Downstream Products

• 1331782-39-8 (R)-3-(piperidin-4-ylmethoxy)-4-(tetrahydrofuran-3-yloxy)benzo[d]isoxazole 4-methylbenzenesulfonate 

Relevant articles and documents

(R)-4-((4-((4-(TETRAHYDROFURAN-3-YLOXY)BENZO[D]ISOXAZOL-3-YLOXY)METHYL)PIPERIDIN-1-YL)METHYL)TETRAHYDRO-2H-PYRAN-4-OL, A PARTIAL AGONIST OF 5-HT4 RECEPTORS

(R)-4-((4-((4-(tetrahydrofuran-3-yloxy)benzo[d]isoxazol-3- yloxy)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-ol and its use in treating neurodegenerative disorders, is described herein.

Synthesis and biological evaluation of D-amino acid oxidase inhibitors

D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a full agonist at the glycine site of the NMDA receptor. A series of benzo[d]isoxazol-3-ol derivatives were synthesized and evaluated as DAAO inhibitors. Among them,

Benzo[d]isoxazol-3-ol DAAO inhibitors

Methods for increasing D-Serine concentration and reducing concentration of the toxic products of D-Serine oxidation, for enhancing learning, memory and/or cognition, or for treating schizophrenia, Alzheimer's disease, ataxia, or neuropathic pain, or preventing loss in neuronal function characteristic of neurodegenerative diseases involve administering to a subject in need of treatment a therapeutic amount of a compound of formula I, or a pharmaceutically acceptable salt or solvate thereof: wherein Z1 is N or CR3; Z2 is N or CR4; Z3is O or S; A is hydrogen, alkyl or M+; M is aluminum, calcium, lithium, magnesium, potassium, sodium, zinc or a mixture thereof; R1, R2, R3 and R4 are independently selected from hydrogen, alkyl, hydroxy alkoxy, aryl, acyl, halo, cyano, haloalkyl, NHCOOR5 and SO2NH2; R5 is aryl, arylalkyl, heteroaryl or heteroarylalkyl; at least one of R1, R2, R3 and R4 is other than hydrogen; and at least one of Z1 and Z2 is other than N.

BENZISOXAZOLES

The present invention concerns the compounds of formula (I), the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein m represents an integer from 1 to 3; X represents amino, hydroxy, -oxo or -Z-R1; Y is absent when X represents -Z-R1 and -(C=O)-R66 when X represents oxo; Z represents carbonyl, -oxy-carbonyl- or -NR 55-carbonyl-; R1 represents C1-4alkyl, Ar1, Ar1-C1-4a1ky1-, -NR3R4 or -Het1; R2 represents hydrogen, halo, nitro, hydroxycarbonyl-, C1-4alkyloxy or C1-4alkyl; R33 and R4 are each independently selected from hydrogen, Ar33 or C1-4alkyl; R5 represents hydrogen, C1-4alkylcarbonyl- or Ar4-carbonyl-; R6 represents a substituent selected from the group consisting of C1.4alkyl, Ar55, Ar6-C1-4alkyl- or NR7R8; R7 and R8 are each independently selected from hydrogen, Het4 or C1-4alkyl; Het1 represents a heterocycle selected from oxazolyl, isoxazolyl, imidazolyl or pyrazolyl wherein said heterocycle is optionally substituted with one, two or three substituents selected from the group consisting of amino, C1-4alkyl, hydroxy-C1-4alkyl, phenyl, phenyl-C1-4alkyl- and phenyl substituted with one or more halo substituents; Het4 represents a heterocycle selected from oxazolyl or isoxazolyl, wherein said heterocycle is optionally substituted with one or more substituents selected from the group consisting of amino, C1-4alkyl, hydroxy-C1-4alkyl-, phenyl, phenyl-Cl-4alkyl and phenyl substituted with one or more halo substituents; and Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6 each independently represents phenyl optionally substituted one or where possible two or more substituents selected from halo, nitro, C1-4alkyl, hydroxy or C1-4alkyloxy-.

Isoxazole derivatives

An isoxazole compound having the following formula: wherein R1 represents hydrogen, halogen, alkyl, alkoxy, hydroxyl, alkylthio, amino, alkanoyl, alkanoylamino, alkanoyloxy, alkoxycarbonyl, carboxy, (alkylthio)thiocarbonyl, carbamoyl, nitro or cyano; R2 represents an amino; m is 1; n is 1 to 6; ring A represents a phenyl ring or a naphthyl ring; and X represents oxygen or sulfur. The isoxazole compound has an excellent monoamine oxidase inhibitory activity, and is useful for treating Parkinson's disease, depression and Alzheimer's disease.