5-Styrylisoxazoles: π-Conjugated System with Fluorescent Properties and Bioactivity

A simple two-step protocol for the synthesis of 3-aryl/hetaryl-4-nitro-5-styrylisoxazole was elaborated. A large series of novel 5-styrylisoxazoles (36 compounds) containing various substituents at positions 3 and 5 of isoxazole cycle was obtained. The title compounds revealed fluorescent properties in visible region, possessing emission maximum up to 610nm. The effect of solvatochromism and chemosensor properties towards a number of metal cations were demonstrated. Cytotoxic activity against MCF-7 (breast carcinoma), HCT-116 (colon carcinoma), A549 (pulmonary carcinoma) and WI38 (fibroblasts from lung tissue) cell lines was tested and toxicity in the concentration range of 10-100 mu M was found for several compounds.

Automated summary

A simple two-step protocol was developed for the synthesis of 3-aryl/hetaryl-4-nitro-5-styrylisoxazole, resulting in a large series of novel 5-styrylisoxazoles with various substituents. These compounds exhibited fluorescent properties in the visible region, with emission maximum up to 610nm. Additionally, they demonstrated solvatochromism and chemosensor properties towards multiple metal cations. Cytotoxic activity against various cancer cell lines was tested, showing toxicity for some compounds in the concentration range of 10-100 μM.