Synthesis and antiproliferative activity of imidazo[1,2-a]pyrimidine Mannich bases

Aeluri, Raghunath; Manjula, A.; Polepalli, Sowjanya; Jain, Nishant

doi:10.1016/j.ejmech.2015.05.037

Cited by 56 publications

(24 citation statements)

References 34 publications

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“…Imidazo[1,2- a ]pyrimidine is an important core with a wide range of biological activity, including antitumor [ 1 , 2 , 3 ], antihyperglycemic [ 4 ], antitubercular [ 5 ], antiviral [ 6 , 7 ], anti-HIV [ 8 ], and antiatherosclerosis [ 9 ]. There are reports on the application of imidazo[1,2- a ]pyridine derivatives as antifungal agents [ 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines

Gómez-García

Andrade-Pavón²,

Campos-Aldrete

et al. 2018

Molecules

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A series of 3-benzoyl imidazo[1,2-a]pyrimidines, obtained from N-heteroarylformamidines in good yields, was tested in silico and in vitro for binding and inhibition of seven Candida species (Candida albicans (ATCC 10231), Candida dubliniensis (CD36), Candida glabrata (CBS138), Candida guilliermondii (ATCC 6260), Candida kefyr, Candida krusei (ATCC 6358) and Candida tropicalis (MYA-3404)). To predict binding mode and energy, each compound was docked in the active site of the lanosterol 14α-demethylase enzyme (CYP51), essential for fungal growth of Candida species. Antimycotic activity was evaluated as the 50% minimum inhibitory concentration (MIC50) for the test compounds and two reference drugs, ketoconazole and fluconazole. All test compounds had a better binding energy (range: −6.11 to −9.43 kcal/mol) than that found for the reference drugs (range: 48.93 to −6.16 kcal/mol). In general, the test compounds showed greater inhibitory activity of yeast growth than the reference drugs. Compounds 4j and 4f were the most active, indicating an important role in biological activity for the benzene ring with electron-withdrawing substituents. These compounds show the best MIC50 against C. guilliermondii and C. glabrata, respectively. The current findings suggest that the 3-benzoyl imidazo[1,2-a]pyrimidine derivatives, herein synthesized by an accessible methodology, are potential antifungal drugs.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines

Gómez-García

Andrade-Pavón²,

Campos-Aldrete

et al. 2018

Molecules

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“…Groebke–Blackburn–Bienayme reaction (GBB) of compound 5 with aromatic aldehydes and isocyanides afforded N ‐substituted‐5,7‐diphenyl‐imidazo[1,2‐ a ]pyrimidin‐3‐amines 6a–o in 60%–90% yields. The reaction was performed in refluxing toluene . Accordingly, this condition was applied for the synthesis of 15 different imidazopyrimidines which were fully characterized by 1 H, 13 C‐NMR, and IR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of novel imidazopyrimidin‐3‐amines as anticancer agents

et al. 2016

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Groebke-Blackburn-Bienayme reaction has been utilized for the synthesis of new imidazo[1,2-a]pyrimidine derivatives as novel anticancer agents. The cytotoxic activities of compounds were evaluated against human cancer cell lines including MCF-7, T-47D, and MDA-MB-231, compared with etoposide as the standard drug. Among the tested compounds, hydroxy- and/or methoxy-phenyl derivatives (6a-c and 6k) with IC values of 6.72-14.36 μm were more potent than etoposide against all cell lines. The acridine orange/ethidium bromide double staining and DNA fragmentation studies demonstrated that the cytotoxic effect of 3-hydroxy-4-methoxyphenyl derivative 6c is associated with apoptosis in cancer cells.

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“…Schiff bases are considered as privileged ligands because of their ability to form complexes with a wide range of metal ions resulting in the formation of stable complexes . Hydrazone is a type of Schiff base with an azomethine group and it has a common structural feature with a general formula R 1 CH═ N─ NH─ R 2 , where R 1 and R 2 are aryl, alkyl, cycloalkyl or heterocyclic hydrazones .…”

Section: Introductionmentioning

confidence: 99%

A series of lanthanide complexes with 2‐fluoro‐N'‐(furan‐2‐ylmethylene) benzohydrazide ligand: Synthesis, characterization, luminescent properties and biological evaluation

Ajlouni

Taha

Hijazi

et al. 2018

Applied Organom Chemis

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Lanthanide (III) complexes were synthesized with Schiff base ligand 2-fluoro-N′-(furan-2-ylmethylene) benzohydrazide (L). These complexes were characterized using elemental analysis, molar conductivity measurements, spectral analysis, luminescence and thermogravimetric analysis. The Schiff base ligand is a tridentate chelate and coordinates to the central lanthanide ion with 1:2 metalto-ligand ratio. The conductivity data show a 1:1 electrolytic nature with general formula [LnL 2 (NO 3 ) 2 ]NO 3 . Eu and Tb complexes exhibit the characteristic luminescence emissions of the central metal ions attributed to efficient energy transfer from the ligand to the metal centre. Most of the complexes exhibit antibacterial activity against a number of pathogenic bacteria. Furthermore, the antioxidant activity of the ligand and its Ln (III) complexes was determined using a radical scavenging method, which indicates that the Ln (III) complexes exhibit more effective antioxidant activity than the ligand.

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Synthesis and antiproliferative activity of imidazo[1,2-a]pyrimidine Mannich bases

Cited by 56 publications

References 34 publications

Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines

Synthesis, Molecular Docking, and Antimycotic Evaluation of Some 3-Acyl Imidazo[1,2-a]pyrimidines

Synthesis and biological evaluation of novel imidazopyrimidin‐3‐amines as anticancer agents

A series of lanthanide complexes with 2‐fluoro‐N'‐(furan‐2‐ylmethylene) benzohydrazide ligand: Synthesis, characterization, luminescent properties and biological evaluation

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