623553-27-5

Usage

Molecular structure

2-[2-(1,3-Benzoxazol-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione consists of a benzoxazole ring and an isoindole-dione moiety, which contribute to its unique properties and potential applications.

Pharmaceutical industry

It can be used as a building block for the synthesis of new drug molecules or as an intermediate in the production of dyes and pigments.

Materials science and optoelectronics

Its structure suggests potential use as a fluorescent probe or as a photoactive compound for various applications.

Need for further research

More research and analysis are required to fully understand the potential uses and properties of 2-[2-(1,3-Benzoxazol-2-yl)ethyl]-1H-isoindole-1,3(2H)-dione.

Upstream product

• 615-36-1 2-bromoaniline 
• 3339-73-9 3-phthalimidopropanoic acid 
• 95-55-6 2-amino-phenol 
• 17137-11-0 3-phthalimidopropionyl chloride 

Downstream Products

• 623553-29-7 2-benzoxazol-2-yl-ethylamine 

Relevant academic research and scientific papers

Synthesis and pharmacological characterization of a new benzoxazole derivative as a potent 5-HT3 receptor agonist

N-(2-Benzoxazol-2-yl-ethyl)-guanidine hydrochloride (10) was synthesized and pharmacologically tested. This compound showed high affinity for the 5-HT3 receptor (Ki=0.77 nM) and potently triggered the von Bezold-Jarisch reflex (BJR) in rats with an ED50=0.52 μg/kg iv and intrinsic activity next to 1 (i.a.=0.94). This stimulant effect was abolished by pretreatment with the 5-HT3 receptor antagonist granisetron and was subject to a rapid and pronounced tachyphylaxis, due to desensitization of the peripheric cardiac 5-HT3 receptor. Consequently, 10 acts as an in vivo 5-HT3 antagonist inhibiting the BJR responses evoked by submaximal doses of 5-HT with an ID50=5.8 μg/kg iv.

Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides

A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.