An ultrasound assisted synthesis of spirooxindolo-1,2,4-oxadiazoles via [3+2] cycloaddition reaction and their anti-cancer activity

Abstract

A facile and ultrasound assisted green methodology was adopted to achieve spirooxindolo-1,2,4-oxadiazoles via a [3+2] cycloaddition of aryl nitrile oxides and isatin Schiff bases at room temperature with good yields and lesser reaction times. The proposed procedure avoids traditional column chromatography resulting in good to excellent yields. The synthesized compounds were evaluated for their anti-cancer activity against SK-OV-3, HeLa, HCT-116, DU-145, A549 and HEK-293 cell lines. Two of them showed significant anti-cancer activity against HeLa with IC50 value 10.75±0.39 µM and 12.43±0.77 µM respectively. In vitro anti-cancer activity X-ray structure Molecular docking Good yields up to 85% Less reaction time Column chromatography free

Ultrasound-assisted ionic liquid-mediated green method for synthesis of 1,3-diphenylpyrazole-based spirooxindolopyrrolizidines, their anti-tubercular activity, molecular docking study and ADME predictions

“…[28][29][30][31] Recently as a green methodology, using ultrasonication plenty of organic reactions were performed with notable yield, less reaction time and softer circumstances. 32,33 Compared with traditional methods, this method is more efficient and simpler controllable method. [34][35][36] In addition to the traditional techniques, the synthesis of spirooxindolopyrrolizidines under environmentally friendly conditions has been shown in many articles.…”

Synthesis, Anti-mycobacterial activity, Molecular Docking and ADME analysis of spiroquinoxaline-1,2,4-oxadiazoles via [3+2] cycloaddition reaction under ultrasound irradiation

“…Ribeiro et al reported spiro-1,2,4-oxadiazoles from the mixture of 3-imino-indolin2-one derivative and hydroximoyl chloride derivative in dry dichloromethane (DCM) under a nitrogen atmosphere for 5-12 h [13]. Our previous work by Kanchrana et al reported spiro-1,2,4oxadiazoles from the mixture of isatin Schiff bases and aryl nitrile oxides at room temperature under ultrasonic irradiation in 20 mins [14]. Herein using same methodology we have synthesized spiroquinoxaline-1,2,4-oxadiazoles from aryl nitrile oxides and quinoxaline Schiff bases under ultrasonic irradiation in 15-30 mins.…”