Pd-Catalysed [3 + 2]-cycloaddition towards the generation of bioactive bis-heterocycles/identification of COX-2 inhibitors analysis

• Published in: Organic & biomolecular chemistry Vol. 2; no. 23; pp. 4746 - 4752
• Main Authors: Sathish, Elagandhula, Ansari, Arshad J, Joshi, Gaurav, Pandit, Akansha, Shukla, Monika, Kumari, Neha, Sharon, Ashoke, Verma, Ved Prakash, Sawant, Devesh M
• Format: Journal Article
• Published: 15.06.2022
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d2ob00467d

In the current research, we envisaged the synthesis of bis-heterocycles containing the dihydroisoxazole ring by [3 + 2] cycloaddition of VECs (vinyl ethylene carbonates) and nitrile oxides, assisted by a Pd catalyst. Herein we explored hydroximoyl chlorides as versatile precursors for the in situ generation of nitrile oxides that were exploited to achieve the cycloaddition reaction on a vinyl group of VECs to generate bis-heterocycles. In silico -based studies of bis-heterocycles on the cyclooxygenase (COX) enzyme displayed selective COX-2 inhibition. Pd-catalysed [3 + 2] cycloaddition reaction of VECs and nitrile oxides to access bis-heterocycles was developed. In silico -based studies suggested interaction with COX receptors that may be corroborated biologically in the future.