Montmorillonite K-10 catalyzed green synthesis of 2,6-unsubstituted dihydropyridines as potential inhibitors of PDE4

Montmorillonite K-10 mediated MCR of anilines, arylaldehydes and ethyl-3,3-diethoxypropionate in water afforded 2,6-unsubstituted dihydropyridines depending on the nature of anilines employed. A variety of dihydropyridines were prepared by using this green methodology in good yields and montmorillonite K-10 was found to be an inexpensive and reusable catalyst. The structure elaboration of a representative compound was carried out under Heck conditions. Some of the compounds synthesized showed significant inhibition of PDE4B when tested in vitro. Docking studies indicated that one of the ester moieties of these compounds played a key role in their interactions with the PDE4B protein.

Graphical abstract2,6-unsubstituted dihydropyridines synthesized via montmorillonite K-10 mediated MCR have been identified as a new class of PDE4 inhibitors.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A green synthesis of 2,6-unsubstituted 1,4-DHPs has been achieved. ► Montmorillonite K-10 was found to be a reusable catalyst for this purpose. ► These compounds showed PDE4 inhibitory properties in vitro. ► Docking studies performed using some of the compounds are presented.