Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of benzothiazole derivatives

Gabr, Moustafa T.; El‐Gohary, Nadia S.; El‐Bendary, Eman R.; El‐Kerdawy, Mohamed M.; Ni, Nanting; Shaaban, Mona I.

doi:10.1016/j.cclet.2015.09.004

Cited by 40 publications

(17 citation statements)

References 27 publications

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“…The complete reaction conditions involved in the synthesis of titled compounds 4 a‐l are illustrated in Scheme and Scheme . The Vilsmeier‐Haack formylation of hydrazone achieved the key intermediate 1,3‐disubstituted 4‐functionalized pyrazole ( 1 ), in 7–8 h, which in turn obtained by the condensation of 3‐acetyl coumarin and benzothiazole hydrazine in refluxing methanol in the presence of catalytic amount of glacial acetic acid for 4–5 h ,. Further, the reaction of an aldehyde 1 with thiosemicarbazide 2 and various α ‐bromoketones 3 a‐l by refluxing in ethanol for about 4–6 h in the presence of catalytic amount of glacial acetic acid leads to the target hybrid compounds 4 a‐l in excellent yields (85‐95%).…”

Section: Resultsmentioning

confidence: 99%

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Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

et al. 2018

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In the present study, a series of novel pyrazole‐thiazole hybrids (4a‐l) were designed, synthesized and assessed for their in vitro antimicrobial activity against both Gram‐positive and Gram‐negative pathogenic bacterial and fungal strains. Compounds derived from p‐CH3 phenyl (4b), p‐Br phenyl (4g), 8‐bromocoumarinyl (4k), and 6,8‐dibromocoumarinyl (4l) exhibited promising inhibitory activity against the tested bacterial strains with minimum inhibitory concentration (MIC)/minimum bactericidal concentration (MBC) spectrum of 1.9/7.8 μg/mL to 3.9/7.8 μg/mL. The compounds with p‐CH3 phenyl (4b), p‐OCH3 phenyl (4c), benzo[f]coumarinyl (4j), 8‐bromocoumarinyl (4k) substitutions showed their inhibitory potency against various Candida strains with MIC/minimum fungicidal concentration (MFC) values of 3.9/7.8 μg/mL. Also, anti‐biofilm and toxicity profile of the compounds was also tested. The biofilm inhibition results revealed that the compound 4 j exhibited promising activity with an IC50 value of 11.8 μM against S. aureus MTCC 96, while 4 k showed significant activity against S. aureus MLS16 MTCC 2940, K. planticola MTCC 530 and C. albicans MTCC 3017 with IC50 values of 12, 14 and 16 μM, respectively. The present study has emphasized that thiazole‐pyrazole hybrids with benzothiazole and coumarin scaffolds can be a novel and potent class of molecules with potential biological activities.

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Section: Resultsmentioning

confidence: 99%

“…also showed that benzothiazole containing compounds were more anticandidal than antimicrobial in nature. They further demonstrated that most of the benzothiazole scaffolds containing compounds were cytotoxic due to their low drug score values …”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

et al. 2018

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“…Also, Streptomyces coelicoflavus isolated from soil microbiota produced 1 H-pyrrole-2-carboxylic acid with QSI effect 8 . Synthetic molecules and peptides exhibited QSI activity 9 . Previous studies focused on the effect of some antimicrobials such as aminoglycosides and quinolones on QS of P. aeruginosa.…”

Section: Introductionmentioning

confidence: 99%

Quorum sensing inhibitory activity of sub-inhibitory concentrations of β-lactams

El-Mowafy

Galil

Habib³

et al. 2017

Afr H. Sci.

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Introduction: The virulence factors of Pseudomonas aeruginosa are under the control of quorum sensing (QS) signals. Hence, interference with QS prevents its pathogenesis. Objective: The aim of the present research is to assess the influence of some β-lactam antibiotics on cell communication and the release of different virulence factors. Methods: The minimal inhibitory concentrations of ceftazidime, cefepime and imipenem were evaluated by microbroth dilution method. The effect of sub-inhibitory concentration of the tested antibiotics on QS signals was investigated using reporter strain assay. In addition, different virulence factors (elastase, protease, pyocyanin and hemolysin) were estimated in the presence of their sub-inhibitory concentrations. Results: Low concentrations of ceftazidime, cefepime and imipenem caused significant elimination of the QS signals 3OH-C12-HSL and C4-HSL up to 1/20 MIC. Furthermore, low concentrations of the tested antimicrobials suppressed virulence factors elastase and hemolysin. Moreover, 1/20 of their MICs reduced elastase, protease, pyocyanin and hemolysin. Conclusion: Utilization of β-lactam antibiotics at low concentrations could be an effective approach for prevention and treatment of P. aeruginosa infection.

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“…% Inhibition = (mean OD of untreated group − mean OD of treated group)/mean OD of untreated group) × 100. [ 38 ]…”

Section: Methodsmentioning

confidence: 99%

3′‐(4‐(Benzyloxy)phenyl)‐1′‐phenyl‐5‐(heteroaryl/aryl)‐3,4‐dihydro‐1′H,2H‐[3,4′‐bipyrazole]‐2‐carboxamides as EGFR kinase inhibitors: Synthesis, anticancer evaluation, and molecular docking studies

Nawaz

Alam

Perwez

et al. 2020

Archiv der Pharmazie

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Pyrazoline‐linked carboxamide derivatives were designed, synthesized, and evaluated for potential epidermal growth factor receptor (EGFR) kinase inhibition, anticancer activity, and apoptotic and cardiomyopathy toxicity. Compounds 6m and 6n inhibit EGFR kinase at a concentration of 6.5 ± 2.91 and 3.65 ± 0.54 µM, respectively. Some of these compounds showed effects on proliferation, which were also then evaluated against four different human cancer cell lines, that is, MCF‐7 (breast cancer), A549 (non‐small‐cell lung tumor), HCT‐116 (colon cancer), and SiHa cells (cancerous tissues of the cervix uteri). The results showed that certain synthetic compounds showed significant inhibitor activity; compounds 6m and 6n were more cytotoxic than doxorubicin against A549 cancer cells, with IC50 values of 10.3 ± 1.07 and 4.6 ± 0.57 µM, respectively. Additionally, compounds 6m and 6n induced apoptosis in A549 cancer cells, as evidenced by 4′,6‐diamidino‐2‐phenylindole (DAPI) staining and phase‐contrast microscopy. Potency to induce apoptosis by compound 6n was further confirmed by fluorescence‐activated cell sorting using Annexin V‐FITC and propidium iodide labeling. Compound 6n showed normal cardiomyocytes with no marked sign of pyknotic nuclei in cardiomyopathy and also normal histological appearance of the renal cortex when compared with that of control. Results of molecular docking studies suggested that compounds 6m and 6n can bind to the hinge region of the adenosine triphosphate‐binding site of EGFR kinase, like the standard drug erlotinib. Therefore, the present study suggests that compounds 6m and 6n have potent in vitro antitumor activities against the human non‐small‐cell lung tumor cell line A549, which can be further explored in other cancer cell lines and in animal studies.

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Synthesis, antimicrobial, antiquorum-sensing and cytotoxic activities of new series of benzothiazole derivatives

Cited by 40 publications

References 27 publications

Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

Quorum sensing inhibitory activity of sub-inhibitory concentrations of β-lactams

3′‐(4‐(Benzyloxy)phenyl)‐1′‐phenyl‐5‐(heteroaryl/aryl)‐3,4‐dihydro‐1′H,2H‐[3,4′‐bipyrazole]‐2‐carboxamides as EGFR kinase inhibitors: Synthesis, anticancer evaluation, and molecular docking studies

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