ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Biological potential of vinyl/allyl substituted imidazole-based N-heterocyclic carbene adducts: synthesis, spectral and X-ray crystallographic structural characteristics

Amna Kamal, Ahmad H. Ibrahim, Sawsan S. Al-Rawi, Muhammad Adnan Iqbal, and Haq Nawaz Bhatti

Department of Chemistry, University of Agriculture Faisalabad, Faisalabad, Pakistan

E-mail: adnan.iqbal@uaf.edu.pk

Received: 19 April 2023  Accepted: 29 September 2023

Abstract:

This manuscript describes the synthesis of three new selenium vinyl/allyl adducts (IV–VI), which incorporate imidazolium- N-heterocyclic carbene salts (I–III) are. The characterization was carried out using NMR spectroscopy and elemental analysis. Particularly, for adduct IV, its structural elucidation was further validated through X-ray diffraction. The vinyl/allyl compounds (I–VI) were evaluated toward two different bacterial strains Escherichia coli and staphylococcus aureus. Salt III shows a MIC = 62.5 µg/ mL and its respective adducts VI shows MIC = 31.2 µgmL⁻¹ against Escherichia coli. All the compounds (I–VI) exhibited significant efficacy against S. aureus with MIC value in the range of 31.2–250 µgmL⁻¹. The highest activity is shown by compound VI i-e 31.2 µg/ mL. All the compounds (I–VI) have thrombolytic potential (65.2 ± 0.89–88.2 ± 0.11%), suggesting their viability as effective agents for thrombolysis. Hemolysis showed cytotoxicity in the range of 2.87 ± 0.12 to 5.49 ± 0.28% which demonstrated they have not injurious effect on health and thus safe.

Keywords: Selenium; NHC; Antibacterial; Crystal structure

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-03126-2

Chemical Papers 78 (2) 851–860 (2024)