157640-14-7

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Benzisoxazol-6-amine,3-methyl-(9CI) is used as a synthetic intermediate for the development of various pharmaceuticals. Its unique structure and biological activities contribute to the creation of new drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1,2-Benzisoxazol-6-amine,3-methyl-(9CI) is utilized as a key component in the synthesis of agrochemicals. Its incorporation aids in the development of effective compounds for crop protection and pest control.
Used in Research and Development:
1,2-Benzisoxazol-6-amine,3-methyl-(9CI) is employed as a molecular probe in biological research. Its diverse interactions with biological systems make it a valuable tool for studying various biological processes and mechanisms.
Used in Drug Discovery:
1,2-Benzisoxazol-6-amine,3-methyl-(9CI) is used as a lead compound in drug discovery, where its structural and functional properties are explored for the development of innovative therapeutic agents targeting specific diseases or conditions.

Upstream product

• 145508-92-5 6-acetamido-3-methyl-1,2-benzisoxazole 
• 117933-03-6 6-fluoro-3-methyl-1,2-benzisoxazole 
• 62572-86-5 1-(2,4-dinitrophenyl)ethanone 
• 157640-13-6 4-acetamido-2-hydroxyacetophenone oxime acetate 

Downstream Products

• 145509-02-0 6-benzamido-3-methyl-1,2-benzisoxazole 
• 145509-04-2 6-benzenesulfonamido-3-methyl-1,2-benzisoxazole 
• 945526-04-5 (3-methyl-benzo[d]isoxazol-6-yl)-carbamic acid benzyl ester 
• 145509-03-1 4-[2-(6-Benzoylamino-benzo[d]isoxazol-3-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 145509-05-3 4-[2-(6-Benzenesulfonylamino-benzo[d]isoxazol-3-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis

Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.

Bicyclic heterocyclic anthranilic diamides as ryanodine receptor modulators with insecticidal activity

The diamide insecticides act on the ryanodine receptor (RyR). The synthesis of various bicyclic anthranilic derivatives is reported. Their activity against the insect ryanodine receptor (RyR) and their insecticidal activity in the greenhouse is presented,

ANTIBACTERIAL AGENTS

The present invention provides a compound of Formula (I) Or a pharmaceutically acceptable salt thereof wherein: W is CH2NHC(=Z)R1, C(=Z)NHR2, or CH2het; X is H, C1-6alkyl, or C2-6alkenyl; Y is H, or F; Z is O, or S; R1 is C1-6alkyl, NHC1-6alkyl, C3-7cycloalkyl, C2-6alkenyl, or OC1-4alkyl; R2 is H, C1-4alkyl, or -OC1-4alkyl; and het is a five-(5) or six-(6) membered heterocyclic ring having 1-4 heteroatoms selected from the group consisting of oxygen, sulfur, and nitrogen within the ring, wherein each carbon atom in het is optionally substituted with C1-4alkyl, C2-4alkenyl, C2-4alkynyl, halo, OR3, CN, NO2, NHR3R3, oxo, CF3, OCF3, C(=O)C1-4alkyl, OC(=O)C1-4alkyl, or C(=O)OR3; wherein R3 is H, or C1-4alkyl.

Novel benzisoxazole derivatives as potent and selective inhibitors of acetylcholinesterase

A series of N-benzylpiperidine benzisoxazoles has been developed as potent and selective inhibitors of the enzyme acetylcholinesterase (AChE). The benzisoxazole heterocycle was found to be an appropriate bioisosteric replacement for the benzoyl functionality present in the N-benzylpiperidine class of inhibitors. The title compounds were synthesized by alkylating 3- methyl-1,2-benzisoxazoles with an iodo piperidine derivative as the key step. Benzisoxazoles 1b-j,o displayed potent inhibition of AChE in vitro with IC50's = 0.8-14 nM. Particularly interesting were N-acetyl and morpholino derivatives 1g (IC50 = 3 nM) and 1j (IC50 = 0.8 nM), respectively, which displayed outstanding selectivity for acetyl- over butyrylcholinesterase, in excess of 3 orders of magnitude. N-acetyl 1g also displayed a favorable profile in vivo. This analog showed a dose-dependent elevation of total acetylcholine in mouse forebrain after oral administration with an ED50 = 2.4 mg/kg. In addition, 1g was able to reverse amnesia in a mouse passive avoidance model at doses of 3.2 and 5.6 mg/kg with an average reversal of 89.7%. Molecular dynamics simulations were used to study the possible binding modes of N-benzylpiperidine benzisoxazoles to AChE from Torpedo californica. Key structural insights were obtained regarding the potency of this class of inhibitors. Specifically, Asp-72, Trp-84, Trp-279, Phe-288, and Phe-330 are implicated in the binding of these inhibitors. The N-benzylpiperidine benzisoxazoles may be suitable compounds for the palliative treatment of Alzheimer's Disease.