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.

N-Alkyl-2-[4-(trifluoromethyl)benzoyl]hydrazine-1-carboxamides and Their Analogues: Synthesis and Multitarget Biological Activity

Based on the isosterism concept, we have designed and synthesized homologous N-alkyl-2-[4-(trifluoromethyl)benzoyl]hydrazine-1-carboxamides (from C1 to C18) as potential antimicrobial agents and enzyme inhibitors. They were obtained from 4-(trifluoromethyl)benzohydrazide by three synthetic approaches and characterized by spectral methods. The derivatives were screened for their inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) via Ellman’s method. All the hydrazinecarboxamides revealed a moderate inhibition of both AChE and BuChE, with IC50 values of 27.04–106.75 µM and 58.01–277.48 µM, respectively. Some compounds exhibited lower IC50 for AChE than the clinically used drug rivastigmine. N-Tridecyl/pentadecyl-2-[4-(trifluoromethyl)benzoyl]hydrazine-1-carboxamides were identified as the most potent and selective inhibitors of AChE. For inhibition of BuChE, alkyl chain lengths from C5 to C7 are optimal substituents. Based on molecular docking study, the compounds may work as non-covalent inhibitors that are placed in a close proximity to the active site triad. The compounds were evaluated against Mycobacterium tuberculosis H37Rv and nontuberculous mycobacteria (M. avium, M. kansasii). Reflecting these results, we prepared additional analogues of the most active carboxamide (n-hexyl derivative 2f). N-Hexyl-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amine (4) exhibited the lowest minimum inhibitory concentrations within this study (MIC ≥ 62.5 µM), however, this activity is mild. All the compounds avoided cytostatic properties on two eukaryotic cell lines (HepG2, MonoMac6).

Stabilization of the bicontinuous cubic phase in siloxane-terminated mesogens, 1,2-bis[4′-(n-(oligodimethylsiloxyl)alkoxy)benzoyl]hydrazine

The introduction of oligodimethyl siloxane segments at the termini of the alkyl tails in a chain-core-chain type molecule effectively stabilizes the bicontinuous cubic phase to widen the temperature range and/or to shift it to lower temperatures.

Synthesis, Crystal Structure and Antibacterial Activity of 4-Hydroxy-Benzaldehyde Benzoyl Hydrazone

A new aroylhydrazone compound of 4-hydroxybenzaldehyde benzoyl hydrazone was synthesized through the condensation of 4-hydroxybenzaldehyde and benzoyl hydrazine. The crystal structure was determined by single-crystal X-ray diffraction. It crystallizes in the orthorhombic system, space group Pbca with a=1.5514(3) nm, b=0.9318(16) nm, c=2.2921(4)nm, β=90.00o, Z=8, V=3.3137(10)nm3. Its crystal structure was determined and refined to a final R=0.0567 for 2725 independent reflections. The intermolecular hydrogen bonding interactions, C-O...N and O-H...O-C, connect the molecules into a layered network structure. The compound showed broad spectrum activity against S. aureus, E. Coli and P. Aeruginosa. The compound has the higher activity for Escherichia coli.