Synthesis Characterization and Studying Antibacterial Activity of some New Pyrazol Derivatives

This research involved the conversion of sulfadiazine into compound 2-chloro-N-(4-(N-(pyrimidin-2-yl) sulfamoyl) phenyl) acetamide [A] through the reaction of sulfadiazine with chloroacetyl chloride in the presence of diethylamine in dimethylformamide as solvent. Then prepared the hydrazine derivative of sulfadiazine 2-hydrazinyl-N-(4-(N-(pyrimidin-2-yl) sulfamoyl) phenyl) acetamide [B] through the interaction of compound [A] with hydrazine in dimethylformamide as solvent. Followed by chalcones preparation [C1, C2, C3, C4, and C5] from the reaction of 4-aminoacetophenone with some aromatic aldehydes in a basic medium in absolute ethanol using an ice bath. Pyrazoline derivatives [BC1, BC2, BC3, BC4, and BC5] were prepared from the reaction of the hydrazine derivative of sulfadiazine [B] with chalcones in a basic medium in the presence of absolute ethanol. The pyrazole derivatives [IBC1, IBC2, IBC3, IBC4, and IBC5] were prepared from the reaction of the hydrazine derivative of sulfadiazine [B] with chalcones in the presence of glacial acetic acid and then the product was oxidized using Iodine. Synthesized compounds have been studied by their melting points, and characterized by C.H.N.S analysis, FT-IR and 1H-MNR spectroscopy and studied of biological activity.

Synthesis, DFT, Molecular docking Analysis and Antibacterial, Antioxidant Activities of tri-substituted pyrazoles

Pyrazole and its derivatives are contemplated crucial compounds in heterocyclic chemistry which are also used extensively in organic synthesis. These cycles are known for their biological and pharmacological activities. The present investigation is in the interest of some synthesized derivatives containing the pyrazole moieties. (5-Hydroxy-3,5-dimethyl-4,5-dihydro-pyrazol-1-yl)-pyridin-4-yl-methanone (1) and Furan-2-yl-(5-hydroxy-3,5-dimethyl-4,5-dihydro-pyrazol-1-yl)-methanone (2) were synthesized by cyclocondensation of the 1,3-dicarbonyl with the hydrazine derivative with a simple and rapid approach to obtain substituted pyrazole. All structures of these compounds were elucidated by spectral (1H NMR and 13C NMR) analysis. The antibacterial activity of the synthesized compounds was screened against two Gram-positive and Gram-negative bacteria, and all of them displayed moderate activity. The radical scavenging activity of these compounds were evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH), the synthetic compounds showed moderate antioxidant activities. In addition, the results obtained from antibacterial activity were further explained with the help of DFT and molecular orbital calculations with a basis set 6-311+G (d, p). The synthesized compounds were docked with 6RKV enzymes with the use molecular docking tools and the docking results are explained all interactions amino acid residue of enzyme and compounds.

Synthesis and Characterization of a Mg2+-Selective Probe Based on Benzoyl Hydrazine Derivative and Its Application in Cell Imaging

A simple benzoyl hydrazine derivative P was successfully synthesized and characterized as Mg2+-selective fluorescent probe. The binding of P with Mg2+ caused an obvious fluorescence enhancement at 482 nm. The fluorescent, UV-vis spectra, 1H-NMR, and IR spectra confirmed the formation of P-Mg2+ complex, and the formation of a 1:1 stoichiometry complex was proved by Job’s plot and mass spectrometry. The recognition mechanism of P to Mg2+ was owing to the photoinduced electron transfer effect (PET). The fluorescent response was linear in the range of 0.9–4.0 µM with the detection limit of 0.3 µM Mg2+ in water–ethanol solution (1:9, v:v, pH10.0, 20 mM HEPES). In addition, the results of cell imaging of Mg2+ in Hl-7701 cells was satisfying.

Synthesis and Characterization of New Dihydronaphthalene Candidates as Potent Cytotoxic Agents against MCF-7 Human Cancer Cells

In the present work, a new series of dihydronaphthalene derivatives were synthesized starting with 6-methoxy-1-tetralone 1, and the corresponding hydrazine derivative 2. Reaction of compound 2 with aryl isothiocyanates produced thiosemicarbazides 3a-d, which were reacted with ethyl chloroacetate to give thiazolidinone derivatives 4a-d. Pyrano thiazolecarbonitrile derivatives 5a-f were prepared by heating a mixture of compounds 4a or 4c, aryl aldehydes, and malononitrile utilizing distilled water in the presence of catalytic amount of potassium hydrogen phthalate. Also, treatment of 4a with DMF-DMA under solvent-free conditions gave enaminone derivative 6, which condensed with ethyl acetoacetate or acetylacetone or malononitrile or cyanothioacetamide to give compounds 7-10, respectively. Finally, reaction of the enaminone 6 with 2-aminoimidazol or 2-aminothiazol in the presence of glacial acetic acid produced derivatives 11 and 12, respectively. Cytotoxic evaluation of eleven compounds, against MCF-7 (human breast adenocarcinoma) cell lines, was estimated. Results revealed that five of the examined compounds 5a, 5d, 5e, 10, and 3d showed potent cytotoxic activities recording, IC50 values; 0.93 ± 0.02 , 1.76 ± 0.04 , 2.36 ± 0.06 , 2.83 ± 0.07 , and 3.73 ± 0.09 μM, respectively, which were more potent than the reference used (Saturosporin, IC50 6.08 ± 0.15 μM). The new products were also examined towards normal epithelial breast cells (MCF10A). All of them showed very good safety profile with different degrees and were safer than the reference drug used. Compound 5a was the most effective against MCF-7 cells and was less toxic than Saturosporin by about 18.45-folds towards MCF01A normal cells. All the new compounds were fully characterized by the different spectral and analytical tools. Herein, detailed syntheses, spectroscopic, and biological data are reported.

Hydrazine derivative synthesis by trifluoroacetyl hydrazide alkylation

N′-Alkyl hydrazides were effectively synthesized by routes featuring installation, alkylation, and removal of a trifluoroacetyl group. A set of amino acid derived hydrazides were acylated using trifluoroacetic anhydride, and the resulting trifluoroacetyl hydrazides were alkylated with alcohols in Mitsunobu reactions and with alkyl halides under alkaline conditions. Removal of the trifluoroacetyl group was affected under reductive and hydrolytic conditions to provide the respective N′-alkyl hydrazides. This three-step process may be performed without isolation of intermediates to yield N′-alkyl hydrazide after a single chromatographic purification.

Novel Aminopyrazole Tagged Hydrazones as Anti-Tubercular Agents: Synthesis and Molecular Docking Studies

Background: Pyrazole derivatives have been reported to possess numerous pharmacological activities viz., antiinflammatory, antipsychotic and etc. Our group have disclosed that pyrozole benzamides display potent antibacterial and antitubercular activities. Objective: Synthesis of new pyrazole acetamides which possess hydrazone group to be evaluated for antitubercular activity. Methods: The key intermediate 5-aminopyrazole was synthesized with known procedure which is then converted into chloroacetamide. This compound than resulted hydrazine derivative and finally the converted in to aromatic hydrazones. All the compounds were screened for anti-tubercular activity. Result: All the synthesized compounds have been characterized by their spectral data obtained and subjected for anti-tubercular activity. Among all the twenty tested compounds, three compounds, 5a5, 5b5 and 5b7 have demonstrated MIC value of 3.12 μg/mL against MTB H37Rv. Docking studies revealed important hydrogen bonding interactions with InhA. Conclusion: Three compounds 5a5, 5b5 and 5b7 were found to be most potent among the series of compounds. Docking studies of compounds explained the presence of hydrogen bonding and π-π stacking interactions with InhA. Further synthesis of more such derivatives with optimized groups would produce compounds with more potent anti-tubercular activity.

Unusual redshift due to selective hydrogen bonding between F− ion and sensor motif: a naked eye colorimetric sensor for F− ions in an aqueous environment

Naked-eye sensing of fluoride ion using 2,4-dinitrophenyl hydrazine derivative.

1-Diphenylphosphanyl-2-(diphenylphosphoryl)hydrazine

The title compound, C24H22N2OP2, is an asymmetrically substituted hydrazine derivative bearing a phosphoryl and a phosphanyl substituent. The PNNP backbone has a torsion angle of −131.01 (8)°. In the crystal, molecules form centrosymmetric dimers by intermolecular N—H...O hydrogen bonds, which are further linked into a three-dimensional network by weak C—H...O and C—H...π interactions.