Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

Anas J Rasras; Mohamed El-Naggar; Nesreen A Safwat; Raed A Al-Qawasmeh

doi:10.3762/bjoc.18.63

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

Beilstein J Org Chem. 2022 May 31:18:631-638. doi: 10.3762/bjoc.18.63. eCollection 2022.

Authors

Anas J Rasras¹, Mohamed El-Naggar², Nesreen A Safwat³, Raed A Al-Qawasmeh^{2

4}

Affiliations

¹ Faculty of Science, Department of Chemistry, Al-Balqa Applied University, PO Box 19117, Al-Salt, Jordan.
² College of Sciences, Department of Chemistry, University of Sharjah, Pure and Applied, Chemistry Research Group, PO Box 27272, Sharjah, United Arab Emirates.
³ The Regional Center for Mycology and Biotechnology, Al-Azhar University, Nasr City, Cairo, 11371, Egypt.
⁴ Department of Chemistry, The University of Jordan, Amman 11942, Jordan.

Abstract

A new chemical library based on the hybridization of cholic acid with the heterocyclic moiety 1,3,4-oxadizole was synthesized, and tested for antimicrobial activity against Gram-positive, Gram-negative bacteria, and fungi. Among the synthesized compounds, the most potent derivatives against S. aureus were 4t, 4i, 4p, and 4c with MIC values between 31 and 70 µg/mL, while compound 4p was the most active one against Bacillus subtilis with a MIC value of 70 µg/mL. Interestingly, compounds 4a and 4u exerted selective activity against Gram-positive bacteria. The synthesized compounds showed good activity against A. fumigatus and C. albicans and compound 4v exhibited selective activity against fungi only.

Keywords: Mannich reaction; antibacterial; cholic acid; heterocyclic; oxadiazole.

Grants and funding

The authors acknowledge the generous funding from Deanship of Scientific Research, Al-Balqa Applied University, grant no. 864/2019/2020 and the Center of Advanced Material/RISE at the University of Sharjah, UAE, for logistic support.