Imidazo[1,2-a]pyridine-appended chalcone and Schiff base conjugates: Synthetic, spectrophotometric, biological, and computational aspects
Herein we describe 2-chloroimidazo[1,2-a]pyridine-appended Schiff base and chalcone conjugates, exploring their synthetic, spectrophotometric, biological, and computational aspects. UV–visible study revealed that scaffolds VIc and VIIIa exhibit bathochromic and hypsochromic shifts respectively compa...
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Elsevier
2024-12-01
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| Series: | Chemical Physics Impact |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S266702242400238X |
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| author | Seema R. Jadhav Shailesh S. Gurav Haya Yasin Promila Nagpal Suraj N. Mali |
| author_facet | Seema R. Jadhav Shailesh S. Gurav Haya Yasin Promila Nagpal Suraj N. Mali |
| author_sort | Seema R. Jadhav |
| collection | DOAJ |
| description | Herein we describe 2-chloroimidazo[1,2-a]pyridine-appended Schiff base and chalcone conjugates, exploring their synthetic, spectrophotometric, biological, and computational aspects. UV–visible study revealed that scaffolds VIc and VIIIa exhibit bathochromic and hypsochromic shifts respectively compared to their analogs, due to auxochrome effect. The molecular docking simulations were performed to investigate the binding interactions of motifs with three cancerous target proteins (4HJO, 1M14, and 1M17) and four microbial target proteins. The compound VIIIb exhibited significant anti-lung cancer activity (GI50: 22.3) against the A-459 cell line. Moreover, the synthesized compounds exhibited auspicious antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae, with MIC ranging from 64 to 175 µg/mL. Additionally, in-silico target prediction analysis suggested a considerable likelihood (26.7%) of acting on kinases for compounds VIIIa and VIIIc. In-silico toxicity scrutiny anticipated all compounds as non-fatal and less toxic as they belong to toxicity class 4 (300 < LD50 ≤ 2000). Further structural insights into the synthesized compounds were gained through optimized geometries, FMOs, MEP plots, and global reactivity descriptors (µ, ɳ, S, and ω), aiding in understanding their structural features, potential reactivity, and toxicity. Overall, these results highlight the potential of the prepared moieties as hopeful intrants for further development. |
| format | Article |
| id | doaj-art-0da4504fd8d34d32a63d46b8f17c42fd |
| institution | Kabale University |
| issn | 2667-0224 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Elsevier |
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| series | Chemical Physics Impact |
| spelling | doaj-art-0da4504fd8d34d32a63d46b8f17c42fd2024-11-27T05:03:29ZengElsevierChemical Physics Impact2667-02242024-12-019100694Imidazo[1,2-a]pyridine-appended chalcone and Schiff base conjugates: Synthetic, spectrophotometric, biological, and computational aspectsSeema R. Jadhav0Shailesh S. Gurav1Haya Yasin2Promila Nagpal3Suraj N. Mali4Department of Chemistry, VIVA College, Virar, Maharashtra, India; Corresponding authors.Department of Chemistry, VIVA College, Virar, Maharashtra, India; Corresponding authors.Department of Pharmaceutical Sciences, College of Pharmacy and Health Sciences, Ajman University, Ajman 346, United Arab Emirates; Corresponding authors.Department of Chemistry, VIVA College, Virar, Maharashtra, IndiaSchool of Pharmacy, D. Y. Patil University (Deemed to be University), Navi Mumbai, Maharashtra, India; Corresponding authors.Herein we describe 2-chloroimidazo[1,2-a]pyridine-appended Schiff base and chalcone conjugates, exploring their synthetic, spectrophotometric, biological, and computational aspects. UV–visible study revealed that scaffolds VIc and VIIIa exhibit bathochromic and hypsochromic shifts respectively compared to their analogs, due to auxochrome effect. The molecular docking simulations were performed to investigate the binding interactions of motifs with three cancerous target proteins (4HJO, 1M14, and 1M17) and four microbial target proteins. The compound VIIIb exhibited significant anti-lung cancer activity (GI50: 22.3) against the A-459 cell line. Moreover, the synthesized compounds exhibited auspicious antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Klebsiella pneumoniae, with MIC ranging from 64 to 175 µg/mL. Additionally, in-silico target prediction analysis suggested a considerable likelihood (26.7%) of acting on kinases for compounds VIIIa and VIIIc. In-silico toxicity scrutiny anticipated all compounds as non-fatal and less toxic as they belong to toxicity class 4 (300 < LD50 ≤ 2000). Further structural insights into the synthesized compounds were gained through optimized geometries, FMOs, MEP plots, and global reactivity descriptors (µ, ɳ, S, and ω), aiding in understanding their structural features, potential reactivity, and toxicity. Overall, these results highlight the potential of the prepared moieties as hopeful intrants for further development.http://www.sciencedirect.com/science/article/pii/S266702242400238X2-chloroimidazo[1,2-a]pyridineChalconesSchiff's basesSpectrophotometric studyToxicityMolecular docking |
| spellingShingle | Seema R. Jadhav Shailesh S. Gurav Haya Yasin Promila Nagpal Suraj N. Mali Imidazo[1,2-a]pyridine-appended chalcone and Schiff base conjugates: Synthetic, spectrophotometric, biological, and computational aspects Chemical Physics Impact 2-chloroimidazo[1,2-a]pyridine Chalcones Schiff's bases Spectrophotometric study Toxicity Molecular docking |
| title | Imidazo[1,2-a]pyridine-appended chalcone and Schiff base conjugates: Synthetic, spectrophotometric, biological, and computational aspects |
| title_full | Imidazo[1,2-a]pyridine-appended chalcone and Schiff base conjugates: Synthetic, spectrophotometric, biological, and computational aspects |
| title_fullStr | Imidazo[1,2-a]pyridine-appended chalcone and Schiff base conjugates: Synthetic, spectrophotometric, biological, and computational aspects |
| title_full_unstemmed | Imidazo[1,2-a]pyridine-appended chalcone and Schiff base conjugates: Synthetic, spectrophotometric, biological, and computational aspects |
| title_short | Imidazo[1,2-a]pyridine-appended chalcone and Schiff base conjugates: Synthetic, spectrophotometric, biological, and computational aspects |
| title_sort | imidazo 1 2 a pyridine appended chalcone and schiff base conjugates synthetic spectrophotometric biological and computational aspects |
| topic | 2-chloroimidazo[1,2-a]pyridine Chalcones Schiff's bases Spectrophotometric study Toxicity Molecular docking |
| url | http://www.sciencedirect.com/science/article/pii/S266702242400238X |
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