Ultrasound-assisted one-pot three-component synthesis of new isoxazolines bearing sulfonamides and their evaluation against hematological malignancies

In the present study, following a one-pot two-step protocol, we have synthesized novel sulfonamides-isoxazolines hybrids (3a-r) via a highly regioselective 1,3-dipolar cycloaddition. The present methodology capitalized on trichloroisocyanuric acid (TCCA) as a safe and ecological oxidant and chlorina...

Full description

Bibliographic Details
Main Authors: Aicha Talha, Cécile Favreau, Maxence Bourgoin, Guillaume Robert, Patrick Auberger, Lahcen EL Ammari, Mohamed Saadi, Rachid Benhida, Anthony R. Martin, Khalid Bougrin
Format: Article
Language:English
Published: Elsevier 2021-10-01
Series:Ultrasonics Sonochemistry
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S135041772100290X
Description
Summary:In the present study, following a one-pot two-step protocol, we have synthesized novel sulfonamides-isoxazolines hybrids (3a-r) via a highly regioselective 1,3-dipolar cycloaddition. The present methodology capitalized on trichloroisocyanuric acid (TCCA) as a safe and ecological oxidant and chlorinating agent for the in-situ conversion of aldehydes to nitrile oxides in the presence of hydroxylamine hydrochloride, under ultrasound activation. These nitrile oxides could be engaged in 1,3-dipolar cycloaddition reactions with various alkene to afford the targeted sulfonamides-isoxazolines hybrids (3a-r). The latter were assessed for their antineoplastic activity against model leukemia cell lines (Chronic Myeloid Leukemia, K562 and Promyelocytic Leukemia, HL-60).
ISSN:1350-4177