Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studies
A series of novel arylazo nicotinates compounds, denoted as (3a-k and 5a-d) were synthesized and characterized through the reaction of 3-oxo-arylhydrazonals with various active methylene nitriles using microporous zeolite as a green catalyst. The structure of the newly prepared heterocycles was dete...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2023-05-01
|
| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610323000510 |
| _version_ | 1797804013648871424 |
|---|---|
| author | Mohamed R. Eletmany Marzough Aziz Albalawi Reem A.K. Alharbi Rokaia B. Elamary Abd El-Fattah A. Harb Moghraby A. Selim Asmaa Sayed Abdelgeliel Entesar A. Hassan Islam M. Abdellah |
| author_facet | Mohamed R. Eletmany Marzough Aziz Albalawi Reem A.K. Alharbi Rokaia B. Elamary Abd El-Fattah A. Harb Moghraby A. Selim Asmaa Sayed Abdelgeliel Entesar A. Hassan Islam M. Abdellah |
| author_sort | Mohamed R. Eletmany |
| collection | DOAJ |
| description | A series of novel arylazo nicotinates compounds, denoted as (3a-k and 5a-d) were synthesized and characterized through the reaction of 3-oxo-arylhydrazonals with various active methylene nitriles using microporous zeolite as a green catalyst. The structure of the newly prepared heterocycles was determined using various spectral techniques such as MS, IR, NMR, and elemental analysis. The antibacterial activity of these compounds against Escherichia coli (E. coli) and Bacillus subtilis (B. subtilis) was evaluated, and it was found that all arylazo nicotinate compounds were highly effective against both gram-negative (E. coli) and gram-positive (B. subtilis) bacterial strains. The efficacy of the developed arylazo nicotinate derivatives as antimicrobial agents against E. coli and B. subtilis was evaluated using minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values. Density-functional theory (DFT) was employed to investigate the structure–activity relationships of recently synthesized compounds. Gaussian 09 software was utilized to compute various molecular properties, including the distribution of frontier molecular orbitals (FMO), the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), the energy gap (Eg), as well as several biological activity descriptors such as ionization potential (IP), electron affinity (EA), chemical potential (μ), chemical hardness (η), electronegativity (χ), global softness (S), and electrophilicity index (ω). The results of the FMO calculations revealed that the arylazo nicotinates had effective charge separation and distinct HOMO/LUMO energy levels for each compound, as reflected by the different Eg values. The Eg values were found to have a strong correlation with the antibacterial efficacy against E. coli and B. subtilis. The highest and lowest efficacy among the molecules (3a-k) were observed for compounds 3b (Eg = 3.36 eV) and 3 k (Eg = 2.27 eV), respectively, while the highest and lowest efficacy among the molecules (5a-d) were observed for compounds 5d (Eg = 3.33 eV) and 5c (Eg = 2.94 eV), respectively. |
| first_indexed | 2024-03-13T05:29:42Z |
| format | Article |
| id | doaj.art-aebc476d7927416ab47877ba13281dee |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-03-13T05:29:42Z |
| publishDate | 2023-05-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-aebc476d7927416ab47877ba13281dee2023-06-15T04:54:30ZengElsevierJournal of Saudi Chemical Society1319-61032023-05-01273101647Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studiesMohamed R. Eletmany0Marzough Aziz Albalawi1Reem A.K. Alharbi2Rokaia B. Elamary3Abd El-Fattah A. Harb4Moghraby A. Selim5Asmaa Sayed Abdelgeliel6Entesar A. Hassan7Islam M. Abdellah8Department of Chemistry, Faculty of Science, South Valley University, Qena 83523, Egypt; Polymer and Color Chemistry Program, North Carolina State University, Raleigh 27606, USADepartment of Chemistry, Alwajh College, University of Tabuk, Tabuk 71491, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Taibah University, Al Madinah Al Munawarah 42353, Saudi ArabiaBotany and Microbiology Department, Faculty of Science, South Valley University, Qena 83523, EgyptDepartment of Chemistry, Faculty of Science, South Valley University, Qena 83523, EgyptDepartment of Chemistry, Faculty of Science, South Valley University, Qena 83523, EgyptBotany and Microbiology Department, Faculty of Science, South Valley University, Qena 83523, EgyptDepartment of Chemistry, Faculty of Science, South Valley University, Qena 83523, EgyptDepartment of Chemistry, Faculty of Science, Aswan University, Aswan 81528, Egypt; Corresponding author at: Department of Chemistry, Faculty of Science, Aswan University, Egypt & Postdoctoral researcher at NC State University, Raleigh, USA.A series of novel arylazo nicotinates compounds, denoted as (3a-k and 5a-d) were synthesized and characterized through the reaction of 3-oxo-arylhydrazonals with various active methylene nitriles using microporous zeolite as a green catalyst. The structure of the newly prepared heterocycles was determined using various spectral techniques such as MS, IR, NMR, and elemental analysis. The antibacterial activity of these compounds against Escherichia coli (E. coli) and Bacillus subtilis (B. subtilis) was evaluated, and it was found that all arylazo nicotinate compounds were highly effective against both gram-negative (E. coli) and gram-positive (B. subtilis) bacterial strains. The efficacy of the developed arylazo nicotinate derivatives as antimicrobial agents against E. coli and B. subtilis was evaluated using minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values. Density-functional theory (DFT) was employed to investigate the structure–activity relationships of recently synthesized compounds. Gaussian 09 software was utilized to compute various molecular properties, including the distribution of frontier molecular orbitals (FMO), the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), the energy gap (Eg), as well as several biological activity descriptors such as ionization potential (IP), electron affinity (EA), chemical potential (μ), chemical hardness (η), electronegativity (χ), global softness (S), and electrophilicity index (ω). The results of the FMO calculations revealed that the arylazo nicotinates had effective charge separation and distinct HOMO/LUMO energy levels for each compound, as reflected by the different Eg values. The Eg values were found to have a strong correlation with the antibacterial efficacy against E. coli and B. subtilis. The highest and lowest efficacy among the molecules (3a-k) were observed for compounds 3b (Eg = 3.36 eV) and 3 k (Eg = 2.27 eV), respectively, while the highest and lowest efficacy among the molecules (5a-d) were observed for compounds 5d (Eg = 3.33 eV) and 5c (Eg = 2.94 eV), respectively.http://www.sciencedirect.com/science/article/pii/S1319610323000510ZeoliteArylazo nicotinatesAntibacterial activityDensity-functional theory (DFT) studiesStructure-activity relationship |
| spellingShingle | Mohamed R. Eletmany Marzough Aziz Albalawi Reem A.K. Alharbi Rokaia B. Elamary Abd El-Fattah A. Harb Moghraby A. Selim Asmaa Sayed Abdelgeliel Entesar A. Hassan Islam M. Abdellah Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studies Journal of Saudi Chemical Society Zeolite Arylazo nicotinates Antibacterial activity Density-functional theory (DFT) studies Structure-activity relationship |
| title | Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studies |
| title_full | Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studies |
| title_fullStr | Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studies |
| title_full_unstemmed | Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studies |
| title_short | Novel arylazo nicotinate derivatives as effective antibacterial agents: Green synthesis, molecular modeling, and structure-activity relationship studies |
| title_sort | novel arylazo nicotinate derivatives as effective antibacterial agents green synthesis molecular modeling and structure activity relationship studies |
| topic | Zeolite Arylazo nicotinates Antibacterial activity Density-functional theory (DFT) studies Structure-activity relationship |
| url | http://www.sciencedirect.com/science/article/pii/S1319610323000510 |
| work_keys_str_mv | AT mohamedreletmany novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies AT marzoughazizalbalawi novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies AT reemakalharbi novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies AT rokaiabelamary novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies AT abdelfattahaharb novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies AT moghrabyaselim novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies AT asmaasayedabdelgeliel novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies AT entesarahassan novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies AT islammabdellah novelarylazonicotinatederivativesaseffectiveantibacterialagentsgreensynthesismolecularmodelingandstructureactivityrelationshipstudies |