Synthesis, in silico and antimicrobial activity study of substituted aromatic imines and their corresponding amines
The antimicrobial properties of Schiff bases and their corresponding amines were assessed by exploring the impact of substituent variations on these activities. The present study involved the synthesis of Schiff base compounds and their corresponding sec-amines, characterization, antibacterial testi...
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Elsevier
2025-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624006829 |
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| author | Hanna Abbo Darin Edward Holman Mohamed-Deen Hendricks Christiana Abimbola Salubi Marshall Keyster Salam Titinchi |
| author_facet | Hanna Abbo Darin Edward Holman Mohamed-Deen Hendricks Christiana Abimbola Salubi Marshall Keyster Salam Titinchi |
| author_sort | Hanna Abbo |
| collection | DOAJ |
| description | The antimicrobial properties of Schiff bases and their corresponding amines were assessed by exploring the impact of substituent variations on these activities. The present study involved the synthesis of Schiff base compounds and their corresponding sec-amines, characterization, antibacterial testing, and molecular docking studies. These compounds featured diverse structural components, including alkyl chains, phenyl and methoxy groups. Three of the synthesized compounds are new, viz. N-[(2,3-dimethoxyphenyl) methylene]-1-propanamine (1), N-[(2,3-dimethoxyphenyl)methyl]-1-propanamine (2) and N-[(2,3-dimethoxyphenyl)methylene]-1-butanamine (3). The assessment of antibacterial properties targeted two strains recognized as opportunistic pathogens. Notably, all Schiff base compounds possessing the −C=N moiety exhibited good antibacterial activity against P. aeruginosa and P. agglomerans. Specifically, 1 and 3 demonstrated exceptional effectiveness against the tested bacterial strains, showcasing promising antibacterial capabilities. Furthermore, binding energy calculations revealed that compounds 1 and 3 exhibited binding energies of −3.9, −4.1, and −3.8, −3.9 kcal/mol with respect to P. agglomerans and P. aeruginosa candidate proteins, respectively. This underscores the strong interaction between the synthesized compounds and the bacterial strains, further supporting their potential as potent antimicrobial agents. P. aeruginosa and P. agglomerans were found to be sensitive to both compounds 1 and 3, as well as the standard control ampicillin. The MIC values for P. aeruginosa were 10 mM for 1, and 6 mM for 3. While for P. agglomerans, the MIC values were 6 mM for both 1 and 3. |
| format | Article |
| id | doaj-art-35828f86793440f991b57f3231e37844 |
| institution | Kabale University |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-35828f86793440f991b57f3231e378442025-01-29T05:00:48ZengElsevierResults in Chemistry2211-71562025-01-0113101986Synthesis, in silico and antimicrobial activity study of substituted aromatic imines and their corresponding aminesHanna Abbo0Darin Edward Holman1Mohamed-Deen Hendricks2Christiana Abimbola Salubi3Marshall Keyster4Salam Titinchi5Department of Chemistry, University of the Western Cape, Cape Town, South Africa; Department of Chemistry, College of Science, University of Basrah, IraqDepartment of Biotechnology, University of the Western Cape, Cape Town, South AfricaDepartment of Biotechnology, University of the Western Cape, Cape Town, South AfricaDepartment of Chemistry, University of the Western Cape, Cape Town, South AfricaDepartment of Biotechnology, University of the Western Cape, Cape Town, South Africa; Corresponding authors.Department of Chemistry, University of the Western Cape, Cape Town, South Africa; Corresponding authors.The antimicrobial properties of Schiff bases and their corresponding amines were assessed by exploring the impact of substituent variations on these activities. The present study involved the synthesis of Schiff base compounds and their corresponding sec-amines, characterization, antibacterial testing, and molecular docking studies. These compounds featured diverse structural components, including alkyl chains, phenyl and methoxy groups. Three of the synthesized compounds are new, viz. N-[(2,3-dimethoxyphenyl) methylene]-1-propanamine (1), N-[(2,3-dimethoxyphenyl)methyl]-1-propanamine (2) and N-[(2,3-dimethoxyphenyl)methylene]-1-butanamine (3). The assessment of antibacterial properties targeted two strains recognized as opportunistic pathogens. Notably, all Schiff base compounds possessing the −C=N moiety exhibited good antibacterial activity against P. aeruginosa and P. agglomerans. Specifically, 1 and 3 demonstrated exceptional effectiveness against the tested bacterial strains, showcasing promising antibacterial capabilities. Furthermore, binding energy calculations revealed that compounds 1 and 3 exhibited binding energies of −3.9, −4.1, and −3.8, −3.9 kcal/mol with respect to P. agglomerans and P. aeruginosa candidate proteins, respectively. This underscores the strong interaction between the synthesized compounds and the bacterial strains, further supporting their potential as potent antimicrobial agents. P. aeruginosa and P. agglomerans were found to be sensitive to both compounds 1 and 3, as well as the standard control ampicillin. The MIC values for P. aeruginosa were 10 mM for 1, and 6 mM for 3. While for P. agglomerans, the MIC values were 6 mM for both 1 and 3.http://www.sciencedirect.com/science/article/pii/S2211715624006829Antimicrobial activityIn silicoSec-aminesSchiff baseP. aeruginosaP. agglomerans |
| spellingShingle | Hanna Abbo Darin Edward Holman Mohamed-Deen Hendricks Christiana Abimbola Salubi Marshall Keyster Salam Titinchi Synthesis, in silico and antimicrobial activity study of substituted aromatic imines and their corresponding amines Results in Chemistry Antimicrobial activity In silico Sec-amines Schiff base P. aeruginosa P. agglomerans |
| title | Synthesis, in silico and antimicrobial activity study of substituted aromatic imines and their corresponding amines |
| title_full | Synthesis, in silico and antimicrobial activity study of substituted aromatic imines and their corresponding amines |
| title_fullStr | Synthesis, in silico and antimicrobial activity study of substituted aromatic imines and their corresponding amines |
| title_full_unstemmed | Synthesis, in silico and antimicrobial activity study of substituted aromatic imines and their corresponding amines |
| title_short | Synthesis, in silico and antimicrobial activity study of substituted aromatic imines and their corresponding amines |
| title_sort | synthesis in silico and antimicrobial activity study of substituted aromatic imines and their corresponding amines |
| topic | Antimicrobial activity In silico Sec-amines Schiff base P. aeruginosa P. agglomerans |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624006829 |
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