Table of Contents
Organic Chemistry International
Volume 2016, Article ID 8696817, 10 pages
http://dx.doi.org/10.1155/2016/8696817
Research Article

Synthesis, Structural Elucidation, and Antibacterial Evaluation of Some New Molecules Derived from Coumarin, 1,3,4-Oxadiazole, and Acetamide

1Department of Chemistry, Government College University, Lahore 54000, Pakistan
2Faculty of Pharmacy, University Technology MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
3Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, University Technology MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
4Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan

Received 30 April 2016; Accepted 25 July 2016

Academic Editor: Jonathan White

Copyright © 2016 Shahid Rasool et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Because of the reported biological activities of coumarin, 1,3,4-oxadiazole, and acetamides, some new compounds incorporating these moieties were synthesized and evaluated for their biological potential against Gram-positive and Gram-negative bacteria. In the present work, 4-chlororesorcinol (1) and ethyl acetoacetate (2) were mixed in a strong acidic medium to synthesize 6-chloro-7-hydroxy-4-methyl-2-oxo-2H-chromene (3) which was subjected to the intermolecular cyclization after consecutive three steps to synthesize 5-(6-chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]-1,3,4-oxadiazol-2-thiol (6). A series of acetamoyl electrophiles, 8ao, were synthesized from aralkyl/alkyl/aryl amines, 7ao, in an aqueous basic medium. The final compounds, 9ao, were synthesized by the reaction of compounds 6 and 8ao in DMF/NaH. The synthesized compounds were structurally elucidated by spectral data analysis of IR, 1H-NMR, and EIMS. The most of the synthesized compounds remained moderate to excellent antibacterial agents. The molecules, 9e, 9j, and 9k, were the most efficient ones against all the five bacterial strains taken into account.