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. 2023 Nov 18;17(1):155.
doi: 10.1186/s13065-023-01067-1.

Cu (II)-catalyzed: synthesis of imidazole derivatives and evaluating their larvicidal, antimicrobial activities with DFT and molecular docking studies

Janani Mullaivendhan  1 , Idhayadhulla Akbar  2 , Mansour K Gatasheh  3 , Ashraf Atef Hatamleh  4 , Anis Ahamed  4 , Mohamed Hussain Syed Abuthakir  5 , Raman Gurusamy  6
Affiliations

Cu (II)-catalyzed: synthesis of imidazole derivatives and evaluating their larvicidal, antimicrobial activities with DFT and molecular docking studies

Janani Mullaivendhan et al. BMC Chem. .

Abstract

This paper deals with the evaluation of novel imidazole molecules for their antimicrobial and larvicidal activities. A series of imidazole derivatives 1(a-f) and 2(a-e) were prepared by the Mannich base technique using a Cu(II) catalyst. The Cu(phen)Cl2 catalyst was found to be more effective than other methods. FTIR, elemental analyses, mass spectrometry, 1H NMR, and 13C NMR spectroscopy were performed to elucidate the structures of the synthesised compounds. Antimicrobial and larvicidal activities were investigated for all compounds. The antibacterial activity of compounds (2d) and (2a) were highly active in S.aureus (MIC: 0.25 μg/mL) and K.pneumoniae (MIC: 0.25 μg/mL) compared to ciprofloxacin. Compound (1c) was significantly more effective than clotrimazole in C.albicans (MIC: 0.25 μg/mL). Molecular docking studies of compound 2d showed a higher binding affinity for the 1BDD protein (- 3.4 kcal/mol) than ciprofloxacin (- 4.4 kcal/mol). Compound 1c had a higher binding affinity (- 6.0 kcal/mol) than clotrimazole (- 3.1 kcal/mol) with greater frontier molecular orbital energy and reactivity properties of compound 1c (∆E gap = 0.13 eV). The activity of compound 1a (LD50: 34.9 μg/mL) was more effective in the Culex quinquefasciatus than permethrin (LD50: 35.4 μg/mL) and its molecular docking binding affinity for 3OGN protein (- 6.1 kcal/mol). These newly synthesised compounds can act as lead molecules for the development of larvicides and antibiotic agents.

Keywords: Antibacterial; Antifungal; DFT; Larvicidal activity; Mannich base; Molecular docking.

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Conflict of interest statement

The authors declare that they have no competing interests.

Figures

Fig. 1
Fig. 1
The Structure of typical of (1-methyl-1H-imidazole) based natural products
Scheme 1
Scheme 1
The synthetic route of compounds (1a-f) and (2a-e)
Fig. 2
Fig. 2
Previous and current of structure–activity relationship
Fig. 3
Fig. 3
The molecular docking studies of compound 2d and Ciprofloxacin binding with 1BDD protein
Fig. 4
Fig. 4
The molecular docking studies of compound 1c and Clotrimazole binding with 1AI9 protein
Fig. 5
Fig. 5
The molecular docking studies of compound 1a binding with 3OGN Protein
Fig. 6
Fig. 6
HOMO–LUMO energy diagram of 2c, 2a, 1c
Fig. 7
Fig. 7
Electrostatic potential Map 2c, 2a and 1c
Fig. 8
Fig. 8
Electron density 2c, 2a and 1c
See this image and copyright information in PMC

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