Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors

Sun, Bin; Li, Kai; Han, Jing; Zhao, Liyu; Su, Xiao Yu; Lin, Bin; Zhao, Dongmei; Cheng, Maosheng

doi:10.1016/j.bmc.2015.08.019

Cited by 32 publications

(18 citation statements)

References 30 publications

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“…Among the most commonly used heterocyclic compounds in pharmaceutics and clinical drugs are imidazole, 1,3,4‐thiadiazole, and their derivatives. In recent years, synthesis and characterization studies of bioactive compounds such as imidazole and 1,3,4‐thiadiazole have been steadily increasing . The synthesis of compounds containing these bioactive groups together with various biological activities has received much interest as well .…”

Section: Introductionmentioning

confidence: 99%

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Tahtacı

Karakurt

et al. 2019

Journal of Heterocyclic Chem

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In this study, a new series of substituted imidazo[2,1‐b][1,3,4]thiadiazole derivatives were synthesized. To this end, first 2‐amino‐1,3,4‐thiadiazole derivatives (compounds 2a and 2b), the starting materials, were synthesized with high yields (82% and 79%, respectively). Then imidazo[2,1‐b][1,3,4]thiadiazole derivatives (4–16), the target compounds, were synthesized from reactions of 2‐amino‐1,3,4‐thiadiazole derivatives (2a and 2b) with 2‐bromoacetophenone derivatives (3a–3i) (in yields of 52% to 71%). All of the synthesized compounds were characterized by 1H NMR, 13C NMR, Fourier transform infrared, elemental analysis, mass spectroscopy, and X‐ray diffraction analysis (compounds 4–12, 14, and 15) techniques. In vitro antifungal activity tests were performed for all of the synthesized compounds. Inhibition zones, percentage of inhibition, minimum fungicidal activity, minimum inhibitory concentration, and lethal dose values of the target compounds were determined against some plant pathogens. According to the results of the biological activity tests, all of the synthesized compounds showed moderate to high levels of antifungal activity. Theoretical calculations were performed to support the experimental results. The geometric parameters of selected compounds (5, 6, and 8) were optimized using the density functional theory B3LYP/6‐31G(d) method in the Gaussian 09W package program, and the frontier molecular orbitals (highest occupied molecular orbital–lowest unoccupied molecular orbital) were calculated theoretically. Finally, molecular docking studies were performed for antifungal activity studies of the selected compounds and to determine whether or not these compounds could be inhibitor agents for the 2RKV protein structure.

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Section: Introductionmentioning

confidence: 99%

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Tahtacı

Karakurt

et al. 2019

Journal of Heterocyclic Chem

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“…Synthesis of pyrazole derivatives from hydrazine and 1,3‐dicarbonyl compounds was first reported in 1883 by Knorr . From earlier established protocols, synthesis of 3‐methyl‐1‐phenyl‐5‐pyrazolone can be achieved by various routes such as reflux in glacial acetic acid, reflux in ethanol or heating in the microwave at 120 °C . The time required for synthesis of 3‐methyl‐1‐phenyl‐5‐pyrazolone for different methods is compared in Figure .…”

Section: Resultsmentioning

confidence: 99%

“…In glacial acetic acid at reflux condition 3‐methyl‐1‐phenyl‐5‐pyrazolone forms after 240 mins, whereas in ethanol without any catalyst at reflux condition it requires around 470 mins …”

Section: Resultsmentioning

confidence: 99%

A Unique Blend of Water, DES and Ultrasound for One‐Pot Knorr Pyrazole Synthesis and Knoevenagel‐Michael Addition Reaction

Kamble

Shankarling

2018

ChemistrySelect

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A simple and convenient method for the tandem synthesis of 4, 4-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ol)s via 3-methyl-1-phenyl-5-pyrazolone from aldehyde, phenyl hydrazine and ethyl acetoacetate using combination of Deep Eutectic Solvent (DES) and ultrasound in water is described. Shorter reaction time, easy work up and comparably good yield of desired product are crucial features. One pot Knorr synthesis and Knovenagel-Michael reaction and use of water as solvent make this methodology an alternative to the other approaches. The advantage of applying ultrasound is, it reduces required time and temperature for reaction with improved yield. The DES and water used here recycled five times without considerable loss of activity.

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“…28 Synthetic imidazole have many potential pharmacological uses. 29 Imidazoles due to diverse synthetic properties with varying physical and chemical properties are very exciting surfactant that can be used with living cells. 30 Zinc has a tendency to form bond with nitrogen atom of the imidazole ligand due to the basic character of imidazole and acid character of zinc ion enabling complex formation.…”

Section: Introductionmentioning

confidence: 99%

Nitrogen donor ligand for capping ZnS quantum dots: a quantum chemical and toxicological insight

et al. 2019

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Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors

Cited by 32 publications

References 30 publications

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

A Unique Blend of Water, DES and Ultrasound for One‐Pot Knorr Pyrazole Synthesis and Knoevenagel‐Michael Addition Reaction

Nitrogen donor ligand for capping ZnS quantum dots: a quantum chemical and toxicological insight

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