Synthesis of 2-substituted-N-[4-(1-methyl-4,5-diphenyl-1H-imidazole-2-yl)phenyl]acetamide derivatives and evaluation of their anticancer activity

Özkay, Yusuf; Işıkdağ, İlhan; İncesu, Zerrin; Akalın, Gülşen

doi:10.1016/j.ejmech.2010.04.015

Cited by 122 publications

(44 citation statements)

References 23 publications

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“…General procedure for the synthesis of 2-(4-substitutedmethylphenyl)propionic acid (6a-6n) 2-(4-Bromo-methylphenyl) propionic acid (0.001 mol, 0.243 g) and appropriate (benz)azolylthiol derivative (0.001 mol) were dissolved in acetone. The solution was refluxed at 40 C for 12 h. Acetone was evaporated, residue was washed with water, filtered, dried and recrystallized from ethanol to obtain final products (6a-6n) 46 .…”

Section: Synthesis Of 2-(4-(bromomethyl)phenyl) Propionic Acid (5)mentioning

confidence: 99%

Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents

Gençer

Çevik

Çavuşoğlu

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of 2-(4-substitutedmethylphenyl)propionic acid derivatives (6a-6m) were synthesized, characterized and evaluated for cyclooxygenase (COX) enzyme inhibitory and antimicrobial activity. Test compounds that exhibited good COX inhibition and antibacterial activity were further screened for their cytotoxicity and genotoxicity. Compounds 6h and 6l showed better COX-1 and COX-2 inhibition when compared to ibuprofen. Inhibition potency of these compounds against COX-2 was very close to that of nimesulide. The compounds 6d, 6h, 6l and 6m displayed promising antibacterial property when compared to chloramphenicol. However, the compound 6l was emerged as the best dual COX inhibitory-antibacterial agent in this study. The ADME prediction of the compounds revealed that they may have a good pharmacokinetic profile. Docking results of the compounds 6h and 6l with COX-1 (PDB ID: 1EQG) also exhibited a strong binding profile. ARTICLE HISTORY

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Section: Synthesis Of 2-(4-(bromomethyl)phenyl) Propionic Acid (5)mentioning

confidence: 99%

Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents

Gençer

Çevik

Çavuşoğlu

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In vitro anticancer [26][27][28][29][30][31][32][33][34][35] activity was determined using a standard MTT assay with protocol appropriate for the individual test system (Abdel-Hafez). In brief, exponentially growing cells were plated in 96-well plates (104 cells/well in 100 µL of medium) and incubated for 24 hrs.…”

Section: In Vitro Anticancer Activitiesmentioning

confidence: 99%

Synthesis, Spectral Characterization and Biological Studies of 2-(4-Methoxynaphthalen-1-Yl)-1-(4-Methoxyphenyl)-1H-Phenanthro[9,10-D] Imidazole

Ramanathan¹

2017

Mod Chem Appl

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Synthesised 2-(4-methoxynaphthalen-1-yl)-1-(4-methoxyphenyl)-1H-phenanthro [9,10-d] imidazole has been characterized by 1 H, 13 C NMR and FT-IR spectral analysis and also biological studies were carried out. The imidazole nitrogen containing heterocyclic ring which possesses biological and pharmaceutical importance. The imidazole ring is ionizable aromatic compound, it improves pharmacokinetic characteristics of imidazole molecules and thus used as a medicine to optimize solubility and bioavailability parameters. There are several methods used for the synthesis of imidazole containing compounds and also their various structure reactions offer enormous scope in the field of medicinal chemistry. The imidazole possesses extensive biological activities such as antimicrobial and anticancer activities.

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“…Nitrogen-containing heterocyclic ring generally offers a polarized character and establishes a most efficient interaction with the receptor molecules to produce anticancer effects [1]. Among them, indole is one of the widely reputed scaffolds to identify new drug candidate as anticancer agents [2][3][4].…”

Section: Introductionmentioning

confidence: 99%

“…Objective: Recently, we reported newly synthesized 5H-benzo [2,3] [1,4]oxazepino [5,6-b]indole) derivatives and proved their cytotoxicity against hepatocellular carcinoma specific Hep-G2 cell lines. We attempted herein to describe a reversed-phase high-performance liquid chromatographic method for the determination of three most active compounds 6a, 10a, and 15a in rat plasma to predict their pharmacokinetics parameters before in vivo study.…”

Section: Introductionmentioning

confidence: 99%

Determination of 5h-Benzo[2,3][1,4]oxazepino[5,6-B]indoles in Rat Plasma by Reversed-Phase High-Performance Liquid Chromatographic-Ultraviolet Method: Application to Pharmacokinetic Studies

Singh

Raj

Rai

et al. 2017

Asian J Pharm Clin Res

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Objective: Recently, we reported newly synthesized 5H-benzo [2,3] [1,4]oxazepino [5,6-b]indole) derivatives and proved their cytotoxicity against hepatocellular carcinoma specific Hep-G2 cell lines. We attempted herein to describe a reversed-phase high-performance liquid chromatographic method for the determination of three most active compounds 6a, 10a, and 15a in rat plasma to predict their pharmacokinetics parameters before in vivo study. Methods:A rapid and sensitive reversed-phase high-performance liquid chromatographic was employed for the determination of 6a, 10a, and 15a in rat plasma. Each compound was separated by a gradient elution of acetonitrile and water with 1 mL/min flow rate. The detector was set at 270, 285, and 275 nm for 6a, 10a, and 15a and the recorded elution times were 2.00, 2.87, and 1.88 min, respectively. Results:The calibration curve was linear with R 2 of 0.938, 0.875, and 0.923 over the concentration range of 0.1-50 µg/mL. The inter-and intraday variations of the assay were lower than 12.26%; the average recovery of 6a, 10a, and 15a was 97.31, 92.56, and 95.23 % with relative standard deviation of 2.12%, 3.25%, and 2.28%, respectively. The C max and T max were ~ 46.34, 18.56, and 25.65 µg/mL and 2.0, 4.0, and 4.0 h for 6a, 10a, and 15a, respectively, which indicate a robust method of detection in the present experiment. Conclusion:The study suggests that all of the three compounds have a lower rate of absorption, higher volume of distribution, and lower clearance rate, indicating good therapeutic response for in vivo activity.

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Synthesis of 2-substituted-N-[4-(1-methyl-4,5-diphenyl-1H-imidazole-2-yl)phenyl]acetamide derivatives and evaluation of their anticancer activity

Cited by 122 publications

References 23 publications

Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents

Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents

Synthesis, Spectral Characterization and Biological Studies of 2-(4-Methoxynaphthalen-1-Yl)-1-(4-Methoxyphenyl)-1H-Phenanthro[9,10-D] Imidazole

Determination of 5h-Benzo[2,3][1,4]oxazepino[5,6-B]indoles in Rat Plasma by Reversed-Phase High-Performance Liquid Chromatographic-Ultraviolet Method: Application to Pharmacokinetic Studies

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