Synthesis and biological activity of novel benzothiazole pyridine derivatives

Jemmezi, Faycel; Kether, Fethi Bel Haj; Amri, Ismail; Bassem, Jamoussi; Jameleddine, Khiari

doi:10.9790/5736-07116266

Cited by 16 publications

(9 citation statements)

References 8 publications

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“…The pyrazolo[5,1‐ a ]isoindole derivatives were known to possess antihypotensive and antireproductive activities. Moreover, pyridine derivatives were extensively investigated for their pharmacological uses, some of these compounds showed antimicrobial , insecticidal , antimitotic , antitumor , antimalarial , and anti‐inflammatory activities. Considering these published data and in searching for new compounds of potent antimicrobial and antiquorum‐sensing activities, we are reporting herein the synthesis of new series of isoindoline‐1,3‐dione, pyrazolo[5,1‐ a ]isoindole, and pyridine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial, Antiquorum‐Sensing, and Cytotoxic Activities of New Series of Isoindoline‐1,3‐dione, Pyrazolo[5,1‐a]isoindole, and Pyridine Derivatives

El‐Gohary

Shaaban

2015

Archiv der Pharmazie

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New series of isoindoline-1,3-diones 2-9, pyrazolo[5,1-a]isoindoles 10-14, and pyridines 16-18 were synthesized. Twenty of the synthesized compounds were screened for their antibacterial activity against S. aureus, B. cereus, and E. coli. Compound 5 was proved to be the most active member in this study, showing the highest antibacterial activity against the three selected microorganisms. The antifungal activity of these compounds was also tested against C. albicans and A. flavus 3375. Compounds 4, 5, 8, and 17a exhibited the best antifungal activity against A. flavus 3375. The same compounds were examined for their antiquorum-sensing activity against Ch. violacium ATCC 12472, whereas compound 5 displayed strong antiquorum-sensing activity. The in vitro cytotoxicity testing of compounds 4-9 and 17a against human normal lung fibroblast (W138) cell line revealed that compounds 4, 5, and 8 are the least cytotoxic analogs in this study. In vivo acute toxicity testing of compounds 4, 5, and 8 was performed. The DNA-binding affinity of compounds 4-9 and 17a was also tested and the obtained results showed that all tested compounds have moderate DNA-binding affinity.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial, Antiquorum‐Sensing, and Cytotoxic Activities of New Series of Isoindoline‐1,3‐dione, Pyrazolo[5,1‐a]isoindole, and Pyridine Derivatives

El‐Gohary

Shaaban

2015

Archiv der Pharmazie

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“…Although pyridine itself is not a compound directly useful in medicine, numerous derivatives based on the pyridine scaffold or incorporating pyridine moiety are found among the clinically used pharmaceuticals. Pyridine derivatives compose about 7000 drugs used against many health disorders. − Compounds containing the pyridine ring show a widespread biological activity, including antiamoebic, , analgesic, ,, anticonvulsant, , antibacterial, ,− antifungal, antihistaminic, antimalarial, , antimuscarinic, anticancer, ,,, antidiabetic, , antiinflammatory, antioxidant, antiviral, ,, and those for central nervous system disorders. , Furthermore, some derivatives of pyridine exhibit inhibitory activity. − …”

Section: Introductionmentioning

confidence: 99%

“…Pyridine derivatives compose about 7000 drugs used against many health disorders. 1−3 Compounds containing the pyridine ring show a widespread biological activity, including antiamoebic, 4,5 analgesic, 4,6,7 anticonvulsant, 8,9 antibacterial, 4,10−14 antifungal, 10 antihistaminic, 3 antimalarial, 1,15 antimuscarinic, 16 anticancer, 4,12,17,18 antidiabetic, 4,19 antiinflammatory, 7 antioxidant, 4 antiviral, 4,20,21 and those for central nervous system disorders. 22,23 Furthermore, some derivatives of pyridine exhibit inhibitory activity.…”

Section: ■ Introductionmentioning

confidence: 99%

Calculations of pK_a Values of Selected Pyridinium and Its N-Oxide Ions in Water and Acetonitrile

et al. 2019

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Pyridine, its N-oxide, and their derivatives are exciting classes of organic bases. These compounds show widespread biological activity, and they are often used in synthesis. In this work results on theoretical calculations of acid dissociation constants as pK a of pyridine, its N-oxide, and their derivatives were done based on the thermodynamic cycle in water and acetonitrile. Additionally, gas-phase basicity (GB) and proton affinity (PA) values were computed for systems studied. All pK a values were obtained using B3LYP, M06-2X, and G4MP2 methods in the gas phase, which were combined with the PCM model calculations (at the Hartree–Fock method) and with the use of four different scale factors alpha. Theoretical GB, PA, and pK a values were then compared with the available experimental ones. Results obtained from B3LYP and M06-2X methods are quite similar and compatible with experimental ones in terms of quality with correlation coefficients values R 2 higher than 0.9, whereas results received from G4MP2 deviate strongly. The calculated pK a values are highly sensitive to the scale factors alpha used in the computational procedure. Root-mean-square deviations (RMSD) between both theoretically and experimentally available pK a values of systems studied were also computed. The RMSD values are lower than 0.8 for the best results, suggesting that the theoretical model presented in this work is promising for applications for pK a calculations of different classes of compounds.

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“…Compound 344 was found to be the one that showed the best activity, which is comparable to the activity of tetracycline. This was due to the presence of an aldehyde function, which imparted its tremendous biological activities [ 41 ].…”

Section: Antibacterial Activity Of Heterocyclic Compoundsmentioning

confidence: 99%

Potential Nitrogen-Based Heterocyclic Compounds for Treating Infectious Diseases: A Literature Review

et al. 2022

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Heterocyclic compounds are considered as one of the major and most diverse family of organic compounds. Nowadays, the demand for these compounds is increasing day-by-day due to their enormous synthetic and biological applications. These heterocyclic compounds have unique antibacterial activity against various Gram-positive and Gram-negative bacterial strains. This review covers the antibacterial activity of different heterocyclic compounds with nitrogen moiety. Some of the derivatives of these compounds show excellent antibacterial activity, while others show reasonable activity against bacterial strains. This review paper aims to bring and discuss the detailed information on the antibacterial activity of various nitrogen-based heterocyclic compounds. It will be helpful for the future evolution of diseases to synthesize new and effective drug molecules.

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Synthesis and biological activity of novel benzothiazole pyridine derivatives

Cited by 16 publications

References 8 publications

Synthesis, Antimicrobial, Antiquorum‐Sensing, and Cytotoxic Activities of New Series of Isoindoline‐1,3‐dione, Pyrazolo[5,1‐a]isoindole, and Pyridine Derivatives

Synthesis, Antimicrobial, Antiquorum‐Sensing, and Cytotoxic Activities of New Series of Isoindoline‐1,3‐dione, Pyrazolo[5,1‐a]isoindole, and Pyridine Derivatives

Calculations of pK_a Values of Selected Pyridinium and Its N-Oxide Ions in Water and Acetonitrile

Potential Nitrogen-Based Heterocyclic Compounds for Treating Infectious Diseases: A Literature Review

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Synthesis and biological activity of novel benzothiazole pyridine derivatives

Cited by 16 publications

References 8 publications

Synthesis, Antimicrobial, Antiquorum‐Sensing, and Cytotoxic Activities of New Series of Isoindoline‐1,3‐dione, Pyrazolo[5,1‐a]isoindole, and Pyridine Derivatives

Synthesis, Antimicrobial, Antiquorum‐Sensing, and Cytotoxic Activities of New Series of Isoindoline‐1,3‐dione, Pyrazolo[5,1‐a]isoindole, and Pyridine Derivatives

Calculations of pKa Values of Selected Pyridinium and Its N-Oxide Ions in Water and Acetonitrile

Potential Nitrogen-Based Heterocyclic Compounds for Treating Infectious Diseases: A Literature Review

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Calculations of pK_a Values of Selected Pyridinium and Its N-Oxide Ions in Water and Acetonitrile