3-AMINOIMIDAZO[1,2-a] PYRIDINE DERIVATIVES: SYNTHESIS AND ANTIMICROBIAL ACTIVITIES

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dc.contributor.authorDragmeh, Osama
dc.date.accessioned2025-01-21T11:05:03Z
dc.date.available2025-01-21T11:05:03Z
dc.date.issued2024-12-18
dc.descriptionBackground: Worldwide, antimicrobial resistance continues to be a major public health issue. Novel antibacterials with improved activity characteristics are therefore in high demand. Antibacterial is one of the many pharmacological actions of imidazo[1,2-a]pyridines. These bioactive substances are the main ingredients of several widely marketed therapeutic medications, such as Alpidem and Zolpidem. Objectives: Creation of novel 3-amino-6-floroimidazo[1,2-a]pyridine derivatives and evaluation of their effectiveness against five bacterial strains. Methodology: The one-pot Groebke-Blackburn-Bienayme-Three Component Reaction (GBB-3CR) was used in the compound synthesis. Several spectroscopic methods, including infrared (IR), proton nuclear magnetic resonance (1H NMR), and carbon-13 nuclear magnetic resonance (13C NMR), were used to confirm the structure. The assessment of purity also makes use of the High-Performance Liquid Chromatography (HPLC) technology. To evaluate the compounds' effectiveness against S. aureus, S. epidermidis, K. pneumonia, P. aeruginosa, and E. coli, biological experiments were conducted on the produced compounds. Results: The seven synthetic compounds (85-91) were produced with a purity of 88-100%. These compounds (85-91) have been verified for their structural formula using 1H NMR, 13C NMR, and IR spectroscopy. These techniques indicate the GBB-3CR normal product. Biologically, compound 91 exhibited the best inhibitory behavior among the others; the lowest MIC value (15.625 µg/ml) was recorded for compound 91 against E. coli. Moreover, compound 91 works better than Gentamicin against K. pneumoniae. The same observation was reported for compounds 85 and 89 against S. epidermis. It is worth pointing out that compound 89 in this study kills E. coli and S. epidermis at lower concentrations (62.5 µg/mL) than Gentamicin antibiotics 125 µg/mL and 250 µg/mL, respectively. The same observation was noticed for compound 85 against S. epidermis with an MBC value of 62.5 µg/mL. Compounds 91, 89, and 85 have good antibacterial effects due to the substitution on C-2 of 3-amino-6-floroimidazo[1,2-a]pyridine scaffolds, which are 1-methylimidazole, p-trifluoromethylphenyl, and 3,5-dimethoxy-4-hydroxyphenyl, respectively. Conclusions: A straightforward, cost-effective, one-step process was used to create new, promising bioactive chemicals. Additional research on these derivatives might provide more potent compounds that show promise as innovative antibacterial treatment options.
dc.description.abstractBackground: Worldwide, antimicrobial resistance continues to be a major public health issue. Novel antibacterials with improved activity characteristics are therefore in high demand. Antibacterial is one of the many pharmacological actions of imidazo[1,2-a]pyridines. These bioactive substances are the main ingredients of several widely marketed therapeutic medications, such as Alpidem and Zolpidem. Objectives: Creation of novel 3-amino-6-floroimidazo[1,2-a]pyridine derivatives and evaluation of their effectiveness against five bacterial strains. Methodology: The one-pot Groebke-Blackburn-Bienayme-Three Component Reaction (GBB-3CR) was used in the compound synthesis. Several spectroscopic methods, including infrared (IR), proton nuclear magnetic resonance (1H NMR), and carbon-13 nuclear magnetic resonance (13C NMR), were used to confirm the structure. The assessment of purity also makes use of the High-Performance Liquid Chromatography (HPLC) technology. To evaluate the compounds' effectiveness against S. aureus, S. epidermidis, K. pneumonia, P. aeruginosa, and E. coli, biological experiments were conducted on the produced compounds. Results: The seven synthetic compounds (85-91) were produced with a purity of 88-100%. These compounds (85-91) have been verified for their structural formula using 1H NMR, 13C NMR, and IR spectroscopy. These techniques indicate the GBB-3CR normal product. Biologically, compound 91 exhibited the best inhibitory behavior among the others; the lowest MIC value (15.625 µg/ml) was recorded for compound 91 against E. coli. Moreover, compound 91 works better than Gentamicin against K. pneumoniae. The same observation was reported for compounds 85 and 89 against S. epidermis. It is worth pointing out that compound 89 in this study kills E. coli and S. epidermis at lower concentrations (62.5 µg/mL) than Gentamicin antibiotics 125 µg/mL and 250 µg/mL, respectively. The same observation was noticed for compound 85 against S. epidermis with an MBC value of 62.5 µg/mL. Compounds 91, 89, and 85 have good antibacterial effects due to the substitution on C-2 of 3-amino-6-floroimidazo[1,2-a]pyridine scaffolds, which are 1-methylimidazole, p-trifluoromethylphenyl, and 3,5-dimethoxy-4-hydroxyphenyl, respectively. Conclusions: A straightforward, cost-effective, one-step process was used to create new, promising bioactive chemicals. Additional research on these derivatives might provide more potent compounds that show promise as innovative antibacterial treatment options.
dc.identifier.urihttps://hdl.handle.net/20.500.11888/19821
dc.language.isoen
dc.publisherAn-Najah National University
dc.supervisorAl-Maharik, Nawaf
dc.supervisorAlhaj, Nisreen
dc.title3-AMINOIMIDAZO[1,2-a] PYRIDINE DERIVATIVES: SYNTHESIS AND ANTIMICROBIAL ACTIVITIES
dc.title.alternativeمشتقات 3-أمينو إيميدازو[1,2-أ]بيريدين: التخليق والأنشطة المضادة للميكروبات
dc.typeThesis
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