Contemporary development in the synthesis and biological applications of pyridine-based heterocyclic motifs

Desai, N. C.; Monapara, Jahnvi D.; Jethawa, Aratiba M.; Pandit, Unnat

doi:10.1016/b978-0-323-91221-1.00007-5

Cited by 3 publications

(1 citation statement)

References 41 publications

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“… 14 Moreover, pyridine is a is a six-membered heterocyclic entity containing nitrogen atoms while pyrimidine has two nitrogen atoms at its adjacent carbon. Pyridine and pyrimidine derivatives have a wide range of biological activities, i.e., antimicrobial, 15 , 16 anti-inflammatory, 17 antitumor, 18 anticancer, 19 antitubercular, 20 , 21 etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antifungal Ergosterol Inhibition, Antibiofilm Activities, and Molecular Docking on β-Tubulin and Sterol 14-Alpha Demethylase along with DFT-Based Quantum Mechanical Calculation of Pyrazole Containing Fused Pyridine–Pyrimidine Derivatives

Desai,

Khasiya,

Jadeja

et al. 2023

ACS Omega

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Multidrug-resistant fungal infections have become much more common in recent years, especially in immune-compromised patients. Therefore, researchers and pharmaceutical professionals have focused on the development of novel antifungal agents that can tackle the problem of resistance. In continuation to this, a novel series of pyrazole-bearing pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione derivatives (4a–4o) have been developed. These compounds have been screened against Candida albicans, Aspergillus niger, and Aspergillus clavatus. The synthesized compounds were characterized by well-known spectroscopic techniques, i.e., IR, 1H NMR, 13C NMR, and mass spectrometry. In vitro antifungal results revealed that compound 4n showed activity against C. albicans having MIC value of 200 μg/mL. To know the plausible mode of action, the active derivatives were screened for anti-biofilm and ergosterol biosynthesis inhibition activities. The compounds 4h, 4j, 4k, and 4n showed greater ergosterol biosynthesis inhibition than the control DMSO. To comprehend how molecules interact with the receptor, studies of molecular docking of 4k and 4n have been performed on the homology-modeled protein of β-tubulin. The molecular docking revealed that the active compounds 4h, 4j, 4k, 4l, and 4n interacting with the active site amino acid of sterol 14-alpha demethylase (PDB ID: 5v5z) indicate one of the possible modes of action of ergosterol inhibition activity. The synthesized compounds 4c, 4e, 4h, 4i, 4j, 4k, 4l, and 4n inhibited biofilm formation and possessed the potential for anti-biofilm activity. DFT-based quantum mechanical calculations were carried out to optimize, predict, and compare the vibration modes of the molecule 4a.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Antifungal Ergosterol Inhibition, Antibiofilm Activities, and Molecular Docking on β-Tubulin and Sterol 14-Alpha Demethylase along with DFT-Based Quantum Mechanical Calculation of Pyrazole Containing Fused Pyridine–Pyrimidine Derivatives

Desai,

Khasiya,

Jadeja

et al. 2023

ACS Omega

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New pyridine‐based chalcones and pyrazolines with anticancer, antibacterial, and antiplasmodial activities

Ramírez‐Prada,

Rocha‐Ortiz,

Orozco

et al. 2024

Archiv der Pharmazie

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New pyridine‐based chalcones 4a–h and pyrazolines 5a–h (N‐acetyl), 6a–h (N‐phenyl), and 7a–h (N‐4‐chlorophenyl) were synthesized and evaluated by the National Cancer Institute (NCI) against 60 different human cancer cell lines. Pyrazolines 6a, 6c–h, and 7a–h satisfied the pre‐determined threshold inhibition criteria, obtaining that compounds 6c and 6f exhibited high antiproliferative activity, reaching submicromolar GI50 values from 0.38 to 0.45 μM, respectively. Moreover, compound 7g (4‐CH3) exhibited the highest cytostatic activity of these series against different cancer cell lines from leukemia, nonsmall cell lung, colon, ovarian, renal, and prostate cancer, with LC50 values ranging from 5.41 to 8.35 μM, showing better cytotoxic activity than doxorubicin. Furthermore, the compounds were tested for antibacterial and antiplasmodial activities. Chalcone 4c was the most active with minimal inhibitory concentration (MIC) = 2 μg/mL against methicillin‐resistant Staphylococcus aureus (MRSA), while the pyrazoline 6h showed a MIC = 8 μg/mL against Neisseria gonorrhoeae. For anti‐Plasmodium falciparum activity, the chalcones display higher activity with EC50 values ranging from 10.26 to 10.94 μg/mL. Docking studies were conducted against relevant proteins from P. falciparum, exhibiting the minimum binding energy with plasmepsin II. In vivo toxicity assay in Galleria mellonella suggests that most compounds are low or nontoxic.

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Synthesis, evaluation of biological activity and SAR of new thioalkyl derivatives of pyridine

Sh. Dashyan,

Babaev,

Ayvazyan

et al. 2024

Bioorganic Chemistry

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Contemporary development in the synthesis and biological applications of pyridine-based heterocyclic motifs

Cited by 3 publications

References 41 publications

Synthesis, Antifungal Ergosterol Inhibition, Antibiofilm Activities, and Molecular Docking on β-Tubulin and Sterol 14-Alpha Demethylase along with DFT-Based Quantum Mechanical Calculation of Pyrazole Containing Fused Pyridine–Pyrimidine Derivatives

Synthesis, Antifungal Ergosterol Inhibition, Antibiofilm Activities, and Molecular Docking on β-Tubulin and Sterol 14-Alpha Demethylase along with DFT-Based Quantum Mechanical Calculation of Pyrazole Containing Fused Pyridine–Pyrimidine Derivatives

New pyridine‐based chalcones and pyrazolines with anticancer, antibacterial, and antiplasmodial activities

Synthesis, evaluation of biological activity and SAR of new thioalkyl derivatives of pyridine

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