Synthesis of Some New Antimicrobial Thiadiazolyl and Oxadiazolyl Quinoline Derivatives

Rizk, Ola H.; Mahran, Mona A.; El‐Khawass, S. M.; El‐Dine, S. A. Shams; Ibrahim, E. A.

doi:10.1007/s00044-005-0138-7

Cited by 7 publications

(7 citation statements)

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“…), and 599 (aromatic C�C str. ; 1 H NMR (400 MHz, DMSO-d6): δH 6.72 (1H, d, J � 12.25 Hz, H-10), 6.91 (1H, d, J � 12.25 Hz, H-9), 7.16 (2H, m, H-4′, H-5′), 7.44 (2H, m, H-6, H-7), 7.56 (1H, td, H-3′), 7.66 (1H, m, H-2′), 7.78 (2H, m, H-5′,H-6′), 7.94 (1H, t, J � 7.45 Hz, H-8), and 8.14 (1H, s, H-4); 13 C NMR (100 MHz, DMSO-d6): δC 125.7 (C-9), 127.2 (C-4), 127.4 (C-5), 127.9 (C-6), 128.0 (C-3), 128.3 (C-4′), 128.4 (C-8), 129.0 (C-2′, C-6′), 129.1 (C-3′, C-5′), 131.2 (C-10), 133.7 (C-4), 135.9 (C-7), 138.9 (C-11), 146.6 (C-2), and 149.9 (C-8a).…”

Section: E Spectroscopic Data Of (Z)-2-chloro-3-styrylquinoline (5)mentioning

confidence: 99%

“…Quinoline moiety is one of the most important heterocyclic scaffolds present in many classes of biologically active compounds [5]. e quinoline nuclei, known since 1962, displays remarkable pharmacological properties such as antiplasmodium [6], anticancer [7][8][9], antibiotic [4,10], antioxidant [4,11], antimicrobial [12,13], and antiinflamation [13]. Among quinolones, fluoroquinolones were known for their broad-spectrum antimicrobial activities and structural modifications that have resulted in the development of the first-to fifth-generation fluoroquinolone drugs [14,15].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines

Zeleke

Melaku

Belay

et al. 2021

Advances in Pharmacological and Pharmaceutical Sciences

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Emergence of antimicrobial resistance to standard commercial drugs has become a critical public health concern worldwide. Hence, novel antimicrobials with improved biological activities are urgently needed. In this regard, a series of quinoline-stilbene derivatives were synthesized from substituted quinoline and benzyltriphenylphosphonium chloride using Wittig reaction. Furthermore, a novel pinacol of quinoline was synthesized by pinacolinazation of 2-methoxyquinoline-3-carbaldehyde which was achieved by aluminum powder-potassium hydroxide reagent combination at ambient temperature in methanol. The structures of the synthesized compounds were established based on their spectral data. The antibacterial activities of the synthesized compounds were evaluated in vitro by the paper disc diffusion method against two Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis) and two Gram-negative bacteria (Escherichia coli and Salmonella typhimurium). The best activity was displayed by compound 19 against E. coli with an inhibition zone of 16.0 ± 0.82 mm and 14.67 ± 0.94 mm at 500 and 250 μg/mL, respectively. This is close to ciprofloxacin which is used as a positive control. The results of in silico molecular docking evaluation of the compounds against E. coli DNA gyraseB were in good agreement with the in vitro antibacterial analysis. Compounds 19 (−6.9 kcal/mol) and 24 (−7.1 kcal/mol) showed the maximum binding affinity close to ciprofloxacin (−7.3 kcal/mol) used as positive control. Therefore, the antibacterial activity displayed by these compounds is encouraging for further investigation to improve the activities of quinoline-stilbenes by incorporating various bioisosteric groups in one or more positions of the phenyl nuclei for their potential pharmacological use. Findings of the DPPH radical scavenging assay indicated that some of the quinolone stilbenes and pinacol possess moderate antioxidant properties compared to ascorbic acid used as a natural antioxidant.

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Section: E Spectroscopic Data Of (Z)-2-chloro-3-styrylquinoline (5)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines

Zeleke

Melaku

Belay

et al. 2021

Advances in Pharmacological and Pharmaceutical Sciences

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“…Several studies also report a different heterocyclic nucleus with the anti-inflammatory effect [ 11 , 12 , 13 , 14 , 15 ] with the thiazole group being one of them [ 16 , 17 , 18 , 19 , 20 ]. Moreover, the substitution of the carboxylate function of NSAIDs by some azoles groups, thiazole, resulted in an increase in anti-inflammatory activity [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of New Benzophenone Derivatives with In Vivo Anti-Inflammatory Activity through Dual Inhibition of Edema and Neutrophil Recruitment

et al. 2018

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A series of novel benzophenone derivatives containing a thiazole heterocyclic nucleus were designed by molecular hybridization. Molecular docking studies have demonstrated the inhibitory potential of the designed compounds against cyclooxygenase (COX) isoenzymes. These compounds were synthesized, characterized, and evaluated for their anti-inflammatory properties by the croton oil-induced ear edema assay to examine their effect on both prostaglandin (PG) production and neutrophils recruitment. The thiazole derivatives displayed a potent effect in terms of reducing ear edema. The analysis suggested that the presence of 4-phenyl-2-hydrazinothiazole and the absence of C4′-OCH3 on the benzophenone derivative structure are strongly related to the inhibition of PG production. In addition, the derivatives 2e, 3a and 3c concomitantly inhibit PG production and neutrophil recruitment, which may be a mechanism of action better than of common NSAIDs due to their inability to inhibit the neutrophil recruitment. Thus, these compounds can be considered as potential lead compounds toward the development of new anti-inflammatory drugs with an innovating mechanism of action.

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“…On the other hand, quinoline derivatives are known to possess diverse pharmacological properties such as antioxidant 18,19 , antibiotic 20,21 , cardiovascular 22 , anti-TB 23 , antiplatelet 24 , anticancer 25,26 , receptor antagonists 27 , NK3 receptor antagonists-II 28 , anti-inflammatory 29 , antimicrobial 30,31 , selective estrogen receptor modulators (SERMs) 32 and protein kinase inhibitor 33 . Keeping above in mind, we decided to synthesize conjugates of the above-mentioned moieties to study the biological profile of the resulting product.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

Verbanac

Malik

Chand

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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C NMR, and finally mass spectrometry. All the synthesized compounds were evaluated in vitro for their potential antibacterial activity and their preliminary safety profile was assessed through cytotoxicity assay. Additionally, six selected conjugates were evaluated for their antioxidative properties on the basis of density functional theory calculations, using radical scavenging assay (DPPH) and cellular antioxidant assay. The reported results encourage further investigation of selected compounds and are shading light on their potential pharmacological use.

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Synthesis of Some New Antimicrobial Thiadiazolyl and Oxadiazolyl Quinoline Derivatives

Cited by 7 publications

References 0 publications

Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines

Synthesis, Molecular Docking Analysis, and Evaluation of Antibacterial and Antioxidant Properties of Stilbenes and Pinacol of Quinolines

Design and Synthesis of New Benzophenone Derivatives with In Vivo Anti-Inflammatory Activity through Dual Inhibition of Edema and Neutrophil Recruitment

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

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