Details

Autor(en) / Beteiligte

• Talha, Aicha
• Favreau, Cécile
• Bourgoin, Maxence
• Robert, Guillaume
• Auberger, Patrick
• EL Ammari, Lahcen
• Saadi, Mohamed
• Benhida, Rachid
• Martin, Anthony R.
• Bougrin, Khalid

Titel

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

Ist Teil von

• Ultrasonics sonochemistry, 2021-10, Vol.78, p.105748-105748, Article 105748

Ort / Verlag

Netherlands: Elsevier B.V

Erscheinungsjahr

2021

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• •Ultrasound-assisted, one-pot green synthesis of new isoxazolines bearing sulfonamides.•Selective synthesis of isoxazolines using trichloroisocyanuric acid (TCCA) in EtOH-water as solvent.•Good to excellent yields and shorter reaction times under sonication.•Compound 3 h displayed promising cytotoxic activities against K562 and HL-60 cells. 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).