1,2-Benzisoxazole compounds: a patent review (2009 – 2014)

Abstract

More recent examples of structural modification of existing drugs led to the discovery of some promising benzisoxazoles for antipsychotic use. The design of multi-target ligands is important for the manipulation of pharmacological properties and safety profiles for the use of antipsychotics. Benzisoxazoles have been widely used as pharmacophores in the search for novel drug candidates in a variety of therapeutic area. It is fair to assume that the wide and frequent use of benzisoxazoles in drug discovery and development will continue into the future.

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

“…3). [39,40]. The heterocyclic ring structure of 1 shares similarity with the clinically used antibiotics cycloserine and linezolid.…”

Substitutional Diversity-Oriented Synthesis and In Vitro Anticancer Activity of Framework-Integrated Estradiol-Benzisoxazole Chimeras

“…Because of their versatile properties and potential as selective ligands for a variety of macromolecular targets, these bicyclic aromatic ring systems constitute the essential structural motif in a wide range of pharmacologically active compounds, including a number of potential anticancer agents ( Figure 1 ) [ 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Furthermore, the benzisoxazole scaffold is often used as a bioisosteric replacement for the benzoyl group of biologically active molecules [ 10 ].…”

Synthesis and Biological Evaluation of Fused Tricyclic Heterocycle Piperazine (Piperidine) Derivatives As Potential Multireceptor Atypical Antipsychotics

“…This approach takes two separate pharmacophores with distinct pharmacology and integrates them into one molecule with the attributes of both parent molecules. , The privileged structures from known antipsychotic drugs were covered (Figure ): (1) phenylpiperazines, which are known to be important motifs for the functional activity of antipsychotics, the preclinical and clinical tests demonstrated that compounds incorporating the 2,3-dichlorophenylpiperazine and 2-methoxyphenylpiperazine scaffolds are useful in the design of atypical antipsychotics, and (2) benzisoxazoles and benzoisothiazoles, which are important fragments, and some medications containing these moieties have been approved for human clinical use, including atypical antipsychotics (risperidone, paliperidone, ziprasidone, and lurasidone). The activities of the piperazine or piperidine moiety at D 2 and 5-HT 2A receptors followed by similar structural heterocycles have proven useful for antipsychotic efficacy . Moreover, the appropriate linker between the tricyclic heterocycles and the privileged structures is important for new compounds binding to the desired multireceptors (D 2 , D 3 , 5-HT 1A , 5-HT 2A , and 5-HT 6 receptors).…”