Green approach for synthesis of bioactive Hantzsch 1,4-dihydropyridine derivatives based on thiophene moiety via multicomponent reaction

R Soc Open Sci. 2017 Jun 14;4(6):170006. doi: 10.1098/rsos.170006. eCollection 2017 Jun.

Abstract

A novel green and efficient one-pot multicomponent reaction of dihydropyridine derivatives was reported as having good to excellent yield. In the presence of the catalyst ceric ammonium nitrate (CAN), different 1,3-diones and same starting materials as 5-bromothiophene-2-carboxaldehyde and ammonium acetate were used at room temperature under solvent-free condition for the Hantzsch pyridine synthesis within a short period of time. All compounds were evaluated for their in vitro antibacterial and antifungal activity and, interestingly, we found that 5(b-f) show excellent activity compared with Ampicillin, whereas only the 5e compound shows excellent antifungal activity against Candida albicans compared with griseofulvin. The cytotoxicity of all compounds has been assessed against breast tumour cell lines (BT-549), but no activity was found. The X-ray structure of one such compound, 5a, viewed as a colourless block crystal, corresponded accurately to a primitive monoclinic cell.

Keywords: Green approach; Hantzsch reaction; ceric ammonium nitrate; microbial study; one-pot multicomponent reaction; single crystal study.

Associated data

  • figshare/10.6084/m9.figshare.c.3796852
  • Dryad/10.5061/dryad.66gd7