21725-69-9

Basic information

• Product Name: BENZO[D]ISOXAZOL-3-OL
• Synonyms: benzo[d]isoxazol-3(2H)-one;3-Hydroxybenzisoxazole 97%;Benzo[d]isoxazol-3-one;1,2-benzisoxazol-3(2h)-one;1,2-benzisoxazol-3-ol;1,2-benzisoxazolin-3-one;3-HYDROXY-1,2-BENZISOXAZOLE;3-HYDROXYBENZISOXAZOLE
• CAS NO: 21725-69-9
• Molecular Formula: C₇H₅NO₂
• Molecular Weight: 135.12
• Product Categories: Fused Ring Systems
• Mol File: 21725-69-9.mol

Chemical Properties

• Melting Point: 140-142°C
• Boiling Point: 299.867ºC at 760 mmHg
• Flash Point: 135.155ºC
• Appearance: /
• Density: 1.379g/cm3
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: 2-8°C
• PKA: 13.55±0.20(Predicted)
• CAS DataBase Reference: BENZO[D]ISOXAZOL-3-OL(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO[D]ISOXAZOL-3-OL(21725-69-9)
• EPA Substance Registry System: BENZO[D]ISOXAZOL-3-OL(21725-69-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• RTECS: DE4933500
• HazardClass: IRRITANT
• Hazardous Substances Data: 21725-69-9(Hazardous Substances Data)

Usage

Uses

benzo[d]isoxazol-3-ol is a useful research chemical.

InChI:InChI=1/C7H5NO2/c9-7-5-3-1-2-4-6(5)10-8-7/h1-4H,(H,8,9)

Upstream product

• 89-73-6 Salicylhydroxamic acid 
• 89-73-6 salicylhydroxamic acid 
• 16063-88-0 C₉H₉NO₄ 
• 69-72-7 salicylic acid 
• 50-78-2 aspirin 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 119-36-8 methyl salicylate 

Downstream Products

• 16263-52-8 3-chlorobenzisoxazole 
• 87691-89-2 4(1,2-benzisoxazol-3-yl)piperazine 
• 87692-13-5 4-<4-(1,2-benzisoxazol-3-yl)-1-piperazinyl>-1-(4-fluorophenyl)-1-butanone hydrochloride 
• 151864-44-7 2-(2',3',5'-tri-O-benzoyl-α-D-arabinofuranosyl)-1,2-benzisoxazol-3-one 
• 151864-43-6 2-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-1,2-benzisoxazol-3-one 
• 786676-91-3 3-oxo-3H-benzo[d]isoxazole-2-carboxylic acid 4-nitro-phenyl ester 
• 776-70-5 2-N,N-dimethylamino-1,3-benzoxazin-4-one 
• 1612763-44-6 tert-butyl N-(furan-2-ylmethyl)-N-{4-[(3-oxo-2,3-dihydro-1,2-benzoxazol-2-yl)methyl]benzoyl}carbamate 
• 1612763-43-5 2-{[4-(piperidine-1-carbonyl)phenyl]methyl}-2,3-dihydro-1,2-benzoxazol-3-one 
• 66570-86-3 3-benzyloxy-benzo[d]isoxazole 
• 66570-94-3 2-benzylbenzo[d]isoxazol-3(2H)-one 
• 6629-80-7 2-Phenyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one 
• 24603-57-4 3-(3-chloro-benzoyloxy)-benzo[d]isoxazole 
• 24603-56-3 3-(4-chloro-benzoyloxy)-benzo[d]isoxazole 

Relevant articles and documents

Identification of a bacteria-produced benzisoxazole with antibiotic activity against multi-drug resistant Acinetobacter baumannii

The emergence of multi-drug resistant pathogenic bacteria represents a serious and growing threat to national healthcare systems. Most pressing is an immediate need for the development of novel antibacterial agents to treat Gram-negative multi-drug resistant infections, including the opportunistic, hospital-derived pathogen, Acinetobacter baumannii. Herein we report a naturally occurring 1,2-benzisoxazole with minimum inhibitory concentrations as low as 6.25 μg ml?1 against clinical strains of multi-drug resistant A. baumannii and investigate its possible mechanisms of action. This molecule represents a new chemotype for antibacterial agents against A. baumannii and is easily accessed in two steps via de novo synthesis. In vitro testing of structural analogs suggest that the natural compound may already be optimized for activity against this pathogen. Our results demonstrate that supplementation of 4-hydroxybenzoate in minimal media was able to reverse 1,2-benzisoxazole’s antibacterial effects in A. baumannii. A search of metabolic pathways involving 4-hydroxybenzoate coupled with molecular modeling studies implicates two enzymes, chorismate pyruvate-lyase and 4-hydroxybenzoate octaprenyltransferase, as promising leads for the target of 3,6-dihydroxy-1,2-benzisoxazole.

Preparation method of 1,2-benzisothiazole-3-ketone

The invention provides a preparation method of 1,2-benzisothiazole-3-ketone. The preparation method comprises the following steps of dissolving salicylhydroxamic acid into methanol; adding sodium hypochlorite with the concentration being 10 to 20 percent; taking a reaction for 20 to 40s at room temperature; performing dilution by distilled water; performing extraction by ethyl acetate; performing organic phase drying by distillation to obtain slight yellow solid; performing suction filtration to obtain a product of the 1,2-benzisothiazole-3-ketone. The method has the advantages that the synthesis process is simple; the cost is low; green and environment-friendly effects are achieved; the time is short; no byproduct is produced; the yield is as high as more than 82 percent.

A novel method for the synthesis of 1,2-benzisoxazoline-3-one and its application to hypochlorite recognition

The reaction of salicylhydroxamic acid with hypochlorite produces 1,2-benzisoxazoline-3-one, a heterocycle that contains a fluorophore. As a result, this reaction was used as the basis for a new, selective and sensitive fluorescence system for the recognition of hypochlorite. The effectiveness of the method was demonstrated by its use to detect hypochlorite in a disinfectant solution as well as to image hypochlorite in cells.

Chromatography-free, Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids to 3-hydroxybenzisoxazoles

The Mitsunobu reaction has become one of the most powerful tools to alkylate acidic pronucleophiles. A significant caveat of Mitsunobu chemistry, however, is that the reaction mixture is often plagued with purification problems owing to the phosphine oxide and hydrazine dicarboxylate by-products. In addition to the development of more readily separable Mitsunobu reagents, the product's physicochemical properties may be exploited to facilitate purification. In this regard, we present a swift and efficient preparation of 3-hydroxybenzisoxazoles by the Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids, which can be isolated by an acid–base work-up. As expected, a range of functional groups was compatible with the chemistry.

Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy

Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5′-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification.

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-.

Small molecule inhibitors of caspases

The present invention provides compounds having formula (I): and pharmaceutically acceptable derivatives thereof, wherein A, B, D, E, G, J, n, and R1 are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof as caspase inhibitors and for the treatment of disorders caused by excessive apoptotic activity.

PROLINE DERIVATIVES AND USE THEREOF AS DRUGS

The present invention aims at providing compounds having therapeutic effects due to a DPP-IV inhibitory action, and satisfactory as pharmaceutical products. The present inventors have found that derivatives having a substituent introduced into the γ-position of proline represented by the formula (I) wherein each symbol is as defined in the specification, have a potent DPP-IV inhibitory activity, and completed the present invention by increasing the stability.

Muscarinic agonists

Compounds and methods are provided for the treatment of disease conditions in which modification of cholinergic, especially muscarinic m1, m4, or both m1 and m4, receptor activity has a beneficial effect. In the method, an effective amount of a compound is administered to a patient in need of such treatment.

Synthesis of an Optically Active Octahydro-2H-pyridopyrazine Based CNS Agent

A synthesis of an optically active octahydro-2H-pyridopyrazine is presented.The key sequence involved the equilibration of an optically active cis-aldehyde to give the thermodynamic transaldehyde that was trapped by nitromethane anion.