Novel Nicotintaldehyde Derivatives via Pd (0) Catalyzed Suzuki Coupling Approach; Characterization, DFT and Molecular Docking and evaluation of anti-antibiofilm, antiquorum sensing activities against Oral pathogens

Author:

Ullah Aman1,Amin Adnan1,Aiman Ume1,Rab Safia Obaidur2,Rehman Fazal Ur1,Awais Sofia3,Aziz Qaiser4,Adeel Muhammad1,Ullah Niamat1,Ahmad Rashid5

Affiliation:

1. Gomal University

2. King Khalid University

3. IBADAT International University

4. University of Azad Jammu and Kashmir

5. University of Malakand

Abstract

Abstract

A very efficient Pd-built catalytic system for the Suzuki Miyaura SM coupling of nicotinaldehydes were developed under gentle reaction conditions. Analytical techniques included FTIR, Uv-Visible, 1H NMR, and 13C NMR, whereas computational analysis used during the investigation involved density functional (DFT), Molecular docking PASS, ADMET and drug likeness. In the current investigation, new nicotinaldehyde compounds i;e 2-(2,3-dimethylphenyl) nicotinaldehyde DMPN, 2-(3-bromophenyl) nicotinaldehyde BrPN, 2-(4-(tert-butyl)-[1, 1-biphenyl]-4-yl) nicotinaldehyde tBuBPN were synthesized. In computational analysis HOMO-LUMO band gaps (Egap) were obtained in the range of 0.14947–0.15888 eV. By using spectroscopic analysis such as FTIR, Uv-Visible, 1H NMR, and 13C NMR, the structures of new synthesized composites were verified. Molecular docking of compounds revealed stable strong interaction with 1JIJ and 2XET. All drug molecules followed drug likeness rules and PASS analysis revealed significant antimicrobial potential high confidence interval (0.329–0.751). The antimicrobial evaluation of tested molecules revealed significant inhibition of oral pathogens including Pseudomonas aeruginosa, Bacillus chungangensis1, Bacillus paramycoides, Bacillus chungangensis2 and Paenibacillus dendritiformis (MIC 1.56–49.2µg/mL). Further significant antibiofilm were recorded in case of DMPN (1.56–6.24 µg/mL) and M2 (MIC 1.56–6.24 µg/mL), whereas all three compounds presented moderate (54–57%) antiquorum sensing activity. It was therefore concluded that compounds DMPN and BrPN possessed strong activities against oral pathogens.

Publisher

Springer Science and Business Media LLC

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