The synthesis, antimicrobial activity and theoretical calculations of 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline

Vagif  Abbasov; Nargiz  Orujova; Ayaz  Mammadov; Rana  Jafarova; Saida  Ahmadbayova; Sevda  Muradova; Elshan Akhmedov

doi:10.24959/nphj.24.147

Authors

Vagif Abbasov Institute of Petrochemical Processes named after academician Y.H. Mammadaliyev of the Ministry of Science and Education of the Republic of Azerbaijan, Baku Azerbaijan, Azerbaijan https://orcid.org/0009-0003-9270-6624
Nargiz Orujova Petrochemical Processes named after academician Y. H. Mammadaliyev, Baku Azerbaijan, Azerbaijan https://orcid.org/0009-0001-4743-8734
Ayaz Mammadov Institute of Petrochemical Processes named after academician Y. H. Mammadaliyev, Baku Azerbaijan, Azerbaijan
Rana Jafarova Institute of Petrochemical Processes named after academician Y. H. Mammadaliyev, Baku Azerbaijan, Azerbaijan https://orcid.org/0009-0003-1331-4092
Saida Ahmadbayova Institute of Petrochemical Processes named after academician Y. H. Mammadaliyev, Baku Azerbaijan, Azerbaijan https://orcid.org/0000-0003-1672-6394
Sevda Muradova Azerbaijan Medical University, Baku Azerbaijan, Azerbaijan https://orcid.org/0009-0000-2819-6146
Elshan Akhmedov National University of Pharmacy of the Ministry of Health of Ukraine, Kharkiv, Ukraine https://orcid.org/0000-0001-6727-8259

DOI:

https://doi.org/10.24959/nphj.24.147

Keywords:

imidazole, synthesis, microwave, ionic liquid catalysts, antimicrobial activity, theoretical calculations, stability

Abstract

Aim. To synthesize 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline, as well as make theoretical calculations of its structure and study its antimicrobial properties.

Materials and methods. The synthesis procedures were performed in the presence of ionic liquid catalysts and under microwave conditions. The catalysts included 1-butyl-3-methylimidazolehydrosulfate, N-methylpyrrolidone perchlorate, and 1,4-dimethylpiperazinedihydrosulfate ionic liquids. Benzyl, ammonium acetate, p-aminoazobenzene and 4-(dimethylamino)benzaldehyde were taken as reagents. Ethanol was used as a solvent.

Results. The results of the conditions were compared and it was determined that the 1,4-dimethylpiperazinedihydrosulfate catalyst reacted under microwave conditions in a shorter time (19 min) with a higher yield (78.1 %). The structure of the compound synthesized was analyzed by ¹H, ¹³C NMR and IR spectroscopy. The theoretical calculations of the compound were determined using the density functional theory (DFT/B3LYP) method with a basic set of 6-31G(d,p). The geometry of the structure was optimized, bond lengths, angle degrees were given, and important quantum chemical parameters, such as HOMO, LUMO orbitals, reactivity, stability, electrophilicity, electronegativity, chemical softness, chemical hardness were calculated. It was found that the compound had a high stability (∆E = 2.359 eV) and a high biological activity (ω = 5.754 eV). The antimicrobial activity of the sample against bacteria of S. aureus, E. coli, P. aeruginosa, K. pneumoniae, B. anthracoides and C. albicans fungus was studied.

Conclusions. In this work, 4-(4,5-diphenyl-1-(4-(phenyldiazenyl)phenyl)-1H-imidazol-2-yl)-N,N-dimethylaniline has been synthesized from benzyl, ammonium acetate, p-aminoazobenzene and 4-(dimethylamino)benzaldehyde in the presence of microwave and ionic liquid catalysts. It has been determined that 1,4-dimethylpiperazinedihydrosulfate catalyst reacts under microwave conditions in a shorter time (19 min) with a higher yield (78.1 %). The compound has been tested as an antimicrobial agent against bacteria of S. aureus, E. coli, P. aeruginosa, K. pneumoniae, B. anthracoides and C. albicans fungus, showing moderate and higher activity.

Author Biographies

Vagif Abbasov, Institute of Petrochemical Processes named after academician Y.H. Mammadaliyev of the Ministry of Science and Education of the Republic of Azerbaijan, Baku Azerbaijan

Doctor of Chemistry (Dr. habil.), academician, general director

Nargiz Orujova, Petrochemical Processes named after academician Y. H. Mammadaliyev, Baku Azerbaijan

PhD student, senior researcher

Ayaz Mammadov, Institute of Petrochemical Processes named after academician Y. H. Mammadaliyev, Baku Azerbaijan

Candidate of Chemistry (PhD), head of the Department of İnformation and Telecommunication

Rana Jafarova, Institute of Petrochemical Processes named after academician Y. H. Mammadaliyev, Baku Azerbaijan

Doctor of Chemistry (Dr. habil.), professor, head of the Department of Physical and Physicochemical Studies

Saida Ahmadbayova, Institute of Petrochemical Processes named after academician Y. H. Mammadaliyev, Baku Azerbaijan

Candidate of Chemistry (PhD), senior researcher

Sevda Muradova, Azerbaijan Medical University, Baku Azerbaijan

Candidate of Medicine (PhD), senior lecturer

Elshan Akhmedov, National University of Pharmacy of the Ministry of Health of Ukraine, Kharkiv

PhD, Associated Professor of General Chemistry Department

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