Recent Advances in Antimicrobial Activity of Pyrimidines: A Review

JADHAV, PRANALI A; BARAVKAR, ATUL

doi:10.22159/ajpcr.2022.v15i2.43686

Cited by 2 publications

(1 citation statement)

References 28 publications

(18 reference statements)

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“…Analogues based on pyrimidine and its annulated heterocyclic compounds have garnered significant interest due to their diverse biological properties, including antimicrobial [1–3], anti‐inflammatory [4, 5], antioxidant [6, 7], antiviral [8], and antitumour [9–12] effectiveness. Pyrimidines were prominent early in the history of organic chemistry as ‘ m ‐diazines’ arising from uric acid catabolism [13].…”

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confidence: 99%

Synthesis, photophysical properties, anticancer evaluation, and molecular docking studies of new pyrimidine linked 4‐arylidene‐thiazolidin‐4‐ones as potent anticancer agents

Jame

2024

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The reaction of 4‐(chloroacetamido)pyrimidine (1) with ammonium thiocyanate gave 2‐(pyrimidin‐4‐ylimino)thiazolidin‐4‐one (2), which, when condensed with four substituted benzaldehyde analogues, gave the consequent 5‐arylidine‐2‐(pyrimidin‐4‐ylimino)thiazolidin‐4‐ones 3a–d. In addition, the absorbance and fluorescence behaviours of pyrimidinylimino‐thiazolidin‐4‐one hybrids 3a–d in various organic solvents were investigated. The emphasis was on studying UV absorption capacities and the effect of various structural components on photophysical qualities such as the 5‐arylidene‐2‐(pyrimidin‐4‐ylimino)thiazolidin‐4‐ones and N,N‐dimethylamino tail. The cytotoxic effect of four pyrimidinylimino‐thiazolidin‐4‐one hybrids 3a–d on tumour cell lines (HepG2, HCT‐116, PC3, MCF‐7) and a normal cell line (WI38) is investigated in this work. The cytotoxicity was measured by comparing the half‐maximal inhibitory concentration (IC50) to the reference medication, 5‐fluorouracil. The findings indicate that these hybrid compounds had varying cytotoxic effects on the cell lines examined; hybrids 3b and 3c demonstrated significant anticancer activity against MCF‐7 with IC50 values of 7.53 ± 0.43 and 9.17 ± 0.31 μM, respectively. The inhibitory efficacy of various synthesized hybrids on the epidermal growth factor receptor (EGFR) kinase was investigated. EGFR is a crucial target in cancer treatment because inhibiting it may reduce tumour development and proliferation. The IC50 value was used to calculate the inhibitory activity, which is the concentration of inhibitor necessary to induce half‐maximal inhibition of EGFR kinase activity. In addition, the predicted ADME results show that pyrimidinylimino‐thiazolidin‐4‐one hybrids have good pharmacokinetic properties; hybrid 3d is more lipophilic than the other compounds. It has a medium molecular weight, a small number of hydrogen bond acceptors and donors, and a large number of aromatic heavy atoms. Moreover, molecular docking simulations revealed precise information on the interactions of pyrimidinylimino‐thiazolidin‐4‐one hybrids 3a–d and 5‐Fu with their respective protein targets. These interactions point to possible pathways for their biological activities and call for more testing to establish their effectiveness as bioactive molecules or therapeutic candidates.

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Section: Introductionmentioning

confidence: 99%

Synthesis, photophysical properties, anticancer evaluation, and molecular docking studies of new pyrimidine linked 4‐arylidene‐thiazolidin‐4‐ones as potent anticancer agents

Jame

2024

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Design, Synthesis and Antimicrobial Activity of 1,3-Diazine Derivatives

Jadhav¹,

Jagtap

Deodhar

et al. 2023

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Background: Pyrimidines have been shown to possess numerous biological activities, such as antimicrobial, anticancer, anticonvulsant, antiviral, and anti-inflammatory. Objective: Encouraged by these data, the synthesis of 2-((1H-benzo[d]imidazol-2-yl)methylthio)-4- amino-6-phenylpyrimidine-5-carbonitrile (3a-g) was performed. Methods: 4-amino-2-mercapto-6-phenylpyrimidine-5-carbonitrile was dissolved in an aqueous sodium hydroxide solution, and to this clear solution, 2-chloromethyl-1H-benzimidazole in methanol was added, and the reaction mixture was stirred under reflux to get the desired product. The structures of the newly synthesized compounds were confirmed by their physical, chemical, and spectral data. The synthesized derivatives were screened for their in vitro antibacterial activity against Gram-positive bacteria, Staphylococcus aureus and Bacillus subtilis, and Gram-negative bacteria, Escherichia coli and Pseudomonas aeruginosa, by using ciprofloxacin as a reference standard. While, their antifungal activity was evaluated against Aspergillus niger and Candida albicans using fluconazole as a reference drug. The docking study was performed to check the interactions of target compounds (3a-g) with homo sapiens DHFR (PDB: 1S3V), bacterial (S. aureus) DHFR (PDB: 2W9T), and DHPS (PDB: 1AD4) protein. The dock score and binding interactions were recorded. Result: The antimicrobial activity study indicated compounds with chloro (3b), fluoro (3f), and bromo (3g) substituents to show good antibacterial as well as antifungal activity. The docking study revealed that the same compounds, i.e., 3b, 3f, and 3g, showed good dock score and comparable interactions compared to the reference ligand (trimethoprim/sulfadiazine), which confirmed their selectivity. Conclusion: It can be presumed that the synthesized compounds have the capability for further promotion as novel antimicrobial agents.

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Recent Advances in Antimicrobial Activity of Pyrimidines: A Review

Cited by 2 publications

References 28 publications

Synthesis, photophysical properties, anticancer evaluation, and molecular docking studies of new pyrimidine linked 4‐arylidene‐thiazolidin‐4‐ones as potent anticancer agents

Synthesis, photophysical properties, anticancer evaluation, and molecular docking studies of new pyrimidine linked 4‐arylidene‐thiazolidin‐4‐ones as potent anticancer agents

Design, Synthesis and Antimicrobial Activity of 1,3-Diazine Derivatives

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