- A novel one-pot, three-component reaction for the synthesis of isocoumarin-condensed pyrazoles
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The one-pot, three-component reaction of substituted homophthalic anhydrides with hydrazine in DMF as solvent and reactant, at reflux temperature, afforded isochromeno[3,4-c]pyrazole-5(2H)-one derivatives in high yields. The mechanism and roles of the substrates were investigated and it was found that cyclic hydrazides were formed as intermediates.
- Ozcan, Sevil,Dengiz, Cagatay,Deli?meroglu, Murat K.,Sahin, Ertan,Balci, Metin
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- Isoquinolinedione-urea hybrids: Synthesis, antibacterial evaluation, drug-likeness, molecular docking and DFT studies
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In the present study, we applied the molecular hybridization approach to combine isoquinolinedione and urea pharmacophores in the same molecules. The hybrid compounds (IU1-IU14) were obtained by the reaction of 2-aminohomophthalimide and an equivalent amount of various isocyanate derivatives. After confirming the chemical structures and evaluating drug-likeness properties, the synthesized compounds were examined for their antibacterial activities against a wide range of bacteria. The compounds possessing lipophilic halogen substituents showed better activities against Gram-positive bacteria, particularly on Staphylococcus aureus strains. This activity trend was further supported by molecular docking studies in the ATP pocket of S. aureus DNA gyrase. Several important parameters such as, ionization potential (IP), electron affinity (EA), global chemical hardness (η), global softness (σ), and electronegativity (χ) were carried out to gain insights into the structural properties and stabilities of selected active compounds by means of density functional theory (DFT) at the B3LYP functional using basis set B3LYP/6–311G(d,p). Electrostatic potential maps (ESPs) and frontier orbital visualizations were further used to comment on molecular polarity and stability.
- ?zkul, Ceren,Dengiz, Cagatay,Do?an, ?engül Dilem,Gündüz, Miyase G?zde,Han, M. ?hsan,K?prü, Semiha
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- Synthesis and biological profiling of novel isocoumarin derivatives and related compounds
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In the continuation of our study of substituted isocoumarins a series of novel 3-azolyl isocoumarin and their thio derivatives, including some related lactone compounds was prepared and biologically profiled against C. albicans showing moderate activity with MIC values in range of 4-60 μg mL-1, in general. The additional characterisation of selected compounds was carried out by exploring their activity on CYP3A4 and CYP2D6 enzymes, while experiments on mutagenicity were performed by AMES test. The representative isocoumarins 3b, 4a and 4b showed lower inhibitory activity on CYP enzymes, when compared to the reference inhibitors, ketoconazole and quinidine. Compound 4a showed a higher mutagenic potential than the other two compounds. Further characterization included cytotoxicity profiling against normal MRC5 cells.
- Bori?, Ivan,Eri?, Slavica,Kiec-Kononowicz, Katarzyna,Latacz, Gniewomir,Lubelska, Annamaria,Nikodinovi?-Runi?, Jasmina,Savic, Vladimir M.,Simi?, Milena R.,Vojnovi?, Sandra
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p. 639 - 649
(2021/08/21)
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- Synthesis and reactivity of 2,3-dihydro-1H-2,3-benzodiazepine-1,4(5H)-dione
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Based on an orthogonal protective group strategy dealing with N-protected hydrazine, we established for the first time a highly efficient synthetic pathway leading to 2,3-benzodiazepine-1,4-dione. Moreover, the versatile reactivities exhibited by this 2,3
- Bihel, Frederic J.-J.,Hellal, Malik,Bourguignon, Jean-Jacques
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p. 3791 - 3796
(2008/09/17)
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