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

Aicha Talha (1) , Cécile Favreau (2) , Maxence Bourgoin (2) , Guillaume Robert (2) , Patrick Auberger (2) , Lahcen El Ammari (1) , Mohamed Saadi (1) , Rachid Benhida (3, 4) , Anthony R. Martin (4) , Khalid Bougrin (1, 3)

1 UM5 - Université Mohammed V de Rabat [Agdal]
2 C3M - Centre méditerranéen de médecine moléculaire
3 UM6P - Université Mohammed VI Polytechnique [Ben Guerir]
4 ICN - Institut de Chimie de Nice

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).

Mots clés: Sulfonamides-Isoxazolines; One-pot synthesis; Radical processes; Ultrasound; Hematological Malignancies; Sulfonamides-Isoxazolines

Domaines: Chimie

Aicha Talha, Cécile Favreau, Maxence Bourgoin, Guillaume Robert, Patrick Auberger, et al.. Ultrasound-assisted one-pot three-component synthesis of new isoxazolines bearing sulfonamides and their evaluation against hematological malignancies. Ultrasonics Sonochemistry, 2021, 78, pp.105748. ⟨10.1016/j.ultsonch.2021.105748⟩. ⟨hal-03342490⟩