STUDY OF AZO COMPOUNDS DERIVED FROM P-CRESOL LIGAND: SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY

Hutham mahmood Yousif  Al-labban; Adil ibadi  Al-luhaiby; Nuha salman  salih; Widad ibrahem  Yahya; Ahmed Abdul jabbar Jaloob  Aljanaby

doi:10.18006/2021.9(3).401.406

Authors

Hutham mahmood Yousif Al-labban Department of Chemistry, Faculty of Science, University of Kufa, Iraq
Adil ibadi Al-luhaiby Department of Laboratory Investigation, Faculty of Science, University of Kufa, Iraq
Nuha salman salih Department of Chemistry, Faculty of Science, University of Kufa, Iraq
Widad ibrahem Yahya Department of Chemistry, Faculty of Science, University of Kufa, Iraq
Ahmed Abdul jabbar Jaloob Aljanaby Department of Biology, Faculty of Science, University of Kufa, Iraq https://orcid.org/0000-0002-9817-3318

DOI:

https://doi.org/10.18006/2021.9(3).401.406

Keywords:

P-cresol, Azo dyes derivatives, Biological activity, Staphylococcus aureus, Pseudomonas aeruginosa

Abstract

Azo compounds contain two aromatic rings separated by an azo (-N=N-) link. These are versatile molecules that have garnered a lot of interest in both basic and applied research. In this work, synthesis of some Azo dyes derivatives by coupling P-cresol with diazonium salts obtained from p-chloroaniline and p-methoxyaniline. The structure of the synthesized compound has been characterized by using techniques like UV-Vis Spectroscopy, and Fourier-transform infrared spectroscopy (FTIR). In addition, the antimicrobial activity of these synthesized dyes compounds was examined by using the disc diffusion method against gram negative and gram positive bacteria Staphylococcus aureus and Pseudomonas aeruginosa which have been isolated from the patients of wound infection. Further, synthesized compounds showed moderate to significant inhibitory effect at the selected concentrations against the tested microorganisms. The results of antibacterial activities demonstrated that compound p-chloroaniline had good antibacterial activity against S. aureus and P. aeruginosa at the concentration of 300 mg/ml with 8.079 mm and 6.16 mm inhibition zone, diameter respectively. This study synthesized two new compounds viz., p-chloroaniline and p-methoxyaniline, and among these two p-chloroaniline has good anti-bacterial activity against S. aureus. Therefore, this can serve as a new compound for the manufacture of ointment to treat wound infections.

References

Abdallah SM (2012) Metal complexes of azo compounds derived from 4-acetamidophenol and substituted aniline. Arabian Journal of Chemistry 5(2):251-256.

Adam RW, Al-Labban HM, Aljanaby AAJ, Abbas NA (2019) Synthesis, characterization and antibacterial activity of some new of novel 1, 2, 3-Triazol-Chalcone derivatives from N-Acetyl-5H-Dibenzo [b, f] Azepine-5-Carboxamide. Nano Biomedicine and Engineering 11(2):99-110.

Aljanaby AAJ (2013) Antibacterial activity of an aqueous extract of Petroselinumcrispum leaves against pathogenic bacteria isolated from patients with burns infections in Al-najaf Governorate, Iraq. Research on Chemical Intermediates 39(8):3709-14.

Aljanaby AAJ (2018) Antibacterial activity of an aqueous extracts of Alkannatinctoria roots against drug resistant aerobic pathogenic bacteria isolated from patients with burns infections. Russian Open Medical Journal 7(1):1-6.

Aljanaby AAJ, Aljanaby IA (2018) Prevalence of aerobic pathogenic bacteria isolated from patients with burn infection and their antimicrobial susceptibility patterns in Al-Najaf City, Iraq-a three-year cross-sectional study. F1000Research 7(1157):1157.

Alkazily WI, Alasedi KK (2013) Analysis of P-cresol Derivatives by Gas Chromatography. Journal of Analytical Techniques 3(1):19.

Al-Labban HM (2017) Synthesis, characterization and study of biological activity of some new 1, 2, 3, 4-Tetrazole derivatives. Research Journal of Pharmacy and Technology 10(10):3645-52.

Al-labban HM, Aljanaby AAJ (2020) An overview of some heterocyclic organic compounds; synthesis, characterization, thermal properties and antibacterial activity. International Journal of Pharmaceutical Research 1: 2394- 2399.

Al-Zinkee JM, Jarad AJ (2019) Synthesis, spectral studies and microbial evaluation of azo dye ligand complexes with some transition metals. Journal of Pharmaceutical Sciences and Research 11(1): 98-103.

Ekennia AC, Onwudiwe DC, Ume C, Ebenso EE (2015) Mixed ligand complexes of N-methyl-N-phenyl dithiocarbamate: synthesis, characterisation, antifungal activity, and solvent extraction studies of the ligand. Bioinorganic chemistry and Applications 12:913424.

Feng J, Kweon O, Xu H, Cerniglia CE, Chen H (2012) Probing the NADH-and methyl red-binding site of a FMN-dependent azoreductase (AzoA) from Enterococcus faecalis. Biochemistry and Biophysics 520(2):99-107.

Fu X, Wei Z, Xia C, Shen C, Xu J, Yang Y, Wang K, Zhang P (2017) Palladium-Catalyzed Direct Ortho C–O bond construction of Azobenzenes with Iodobenzenediacetate via C–H Activation.Catalysis Letters 147(2):400-6.

Hayder T, Aljanaby AAJ (2019) Antibiotics susceptibility patterns of Citrobacterfreundii isolated from pa-tients with urinary tract infection in Al-Najaf governorate–Iraq. International Journal of Research in Pharmaceutical Sciences 10(2):1481-1488.

Jarad AJ, Majeed IY, Hussein AO (2018) Synthesis and spectral studies of heterocyclic azo dye complexes with some transition metals. Journal of Physics: Conference Series 1003: (1): 012021.

Kassa A (2015) Synthesis, Characterization AND Antimicrobial Activities OF Ni (II)-AND Cu (II)-Complexes OF N-Pyrazolylpropanamide. Palgo Journal of Medicine and Medical Sciences 2(1):24-32.

Kyei SK, Akaranta O, Darko G (2020) Synthesis, characterization and antimicrobial activity of peanut skin extract-azo-compounds. Scientific African 8:e00406.

Majeed HT, Aljanaby AAJ (2019) Antibiotic susceptibility patterns and prevalence of some extended spectrum beta-lactamases genes in gram-negative bacteria isolated from patients infected with urinary tract infections in Al-Najaf City, Iraq. Avicenna Journal of Medical Biotechnology 11(2):192.

Malinović BN, Pavlović MG, Djuričić T (2017) Electrocoagulation of textile wastewater containing a mixture of organic dyes by iron electrode. Journal of Electrochemical Science and Engineering 7(2):103-110.

Mehta KK, Patel AD (2016) Synthesis, characterization, biological and chelating properties of new antipyrine derived azo dyes and its transition metal complexes. ActaChimica and Pharmaceutica Indica 6:26-31.

Mohammed EH, Aljanaby AAJ (2020) Galectin3 and cd16 play an important immunological role in patients infected with salmonella typhi. International Journal of Research in Pharmaceutical Sciences 11(3): 4162–4169.

Sarigul M, Kariper SE, Deveci P, Atabey H, Karakas D, Kurtoglu

M (2017) Multi-properties of a new azo-Schiff base and its binuclear copper (II) chelate: Preparation, spectral characterization, electrochemical, potentiometric and modeling studies. Journal of Molecular Structure 1149:520-9.

Sharma AA, Kasem M, Ali E, Moustafa ME (2014) Synthesis and characterization of some new azo compounds based on 2, 4-dihydroxy benzoic acid. Journal of Basic and Environmental Sciences 1:76-85.

Tomi IH, Al-Daraji AH, Al-Qaysi RR, Hasson MM, Al-Dulaimy KH (2014) Synthesis, characterization and biological activities of some azo derivatives of aminothiadiazole derived from nicotinic and isonicotinic acids. Arabian Journal of Chemistry 7(5):687-94.