Synthesis and antibacterial activity of water-soluble limonin benzoylhydrazone derivatives / 中国药科大学学报

@#As a compound rich in citrus plants, limonin has a wide range of biological activities, but its practical application is limited because of its poor water solubility.In this paper, eight new compounds 7a-7h were designed and synthesized by introducing benzoyl hydrazone at the carbonyl position of limonin.The results showed that the water solubilities of all compounds were higher than that of limonin, especially 7a, 7d, 7e and 7f.In addition, the experiment showed that compounds 7d and 7e with substituted hydroxyl groups at the interposition and para-position of the benzene ring had strong antibacterial effects against Escherichia coli and Staphylococcus aureus, and that compound 7e had the best activity, with minimum inhibitory concentrations of 0.31 mg/mL and 1.25 mg/mL, respectively.And compound 7e had better antibacterial activiy in E.coli than sodium benzoate.

Synthesis of benzoyl hydrazones having 4-hydroxy-3,5-dimethoxy phenyl ring, their biological activities, and molecular modeling studies on enzyme inhibition activities.

Hydrazone compounds have high capacity in terms of antioxidant activity and enzyme inhibition activities such as anticholinesterase, tyrosinase, and urease. In this study, benzoyl hydrazones compounds (7a-7m) were synthesized starting from 3,5-dimethoxy-4-hydroxybenzaldehyde. Antioxidant activity of the synthesized compounds was evaluated. In the ß-carotene-linoleic acid and ABTS cation radical scavenging activities, compounds 7j, 7e, and 7m stood out as the most active compounds, respectively. In the anticholinesterase enzyme inhibition activity results, compound 7f exhibited the best activity against AChE and BChE enzymes in the synthesis series. In addition, molecular docking analysis was performed to understand the inhibition mechanism of the synthesized compounds with target enzymes at the atomic level. In the light of biological activity and in silico studies, it has the potential to guide studies for the development of new drugs for Alzheimer disease in the future.

Crystal structures of two isotypic lanthanide(III) complexes: tri-aqua-[2,6-di-acetyl-pyridine bis-(benzoyl-hydrazone)]methano-llanthanide(III) trichloride methanol disolvates (LnIII = Tb and Dy).

The title lanthanide complexes, [Ln(DAPBH2)(CH3OH)(H2O)3]Cl3·2CH3OH [LnIII = Tb and Dy; DAPBH2 = 2,6-di-acetyl-pyridine bis-(benzoyl-hydrazone), C23H21N5O2], are isotypic. The central lanthanide ions are nine-coordinate, being ligated by three N and two O atoms from the penta-dentate DAPBH2 ligand, and four O atoms from the coordinated methanol mol-ecule and three coordinated water mol-ecules. The coordination geometry of the lanthanide ion is a distorted capped square anti-prism. In the crystals, the various components are linked by O-H⋯Cl, N-H⋯Cl and O-H⋯O hydrogen bonds, forming three-dimensional supra-molecular frameworks. Within the frameworks, there are C-H⋯Cl and C-H⋯O hydrogen bonds and offset π-π inter-actions (inter-centroid distance ca 3.81 Å).

Discovery of N-arylsulfonyl-3-acylindole benzoyl hydrazone derivatives as anti-HIV-1 agents

The discovery and development of novel inhibitors with activity against variants of human immunodeficiency virus type 1 (HIV-1) is pivotal for overcoming treatment failure. As our ongoing work on research of anti-HIV-1 inhibitors, 32 N-arylsulfonyl-3-acylindole benzoyl hydrazone derivatives were prepared by introduction of the hydrazone fragments on the N-arylsulfonyl-3-acylindolyl skeleton and preliminarily screened in vitro as HIV-1 inhibitors for the first time. Among of all the reported analogues, eight compounds exhibited significant anti-HIV-1 activity, especially N-(3-nitro)phenylsulfonyl-3-acetylindole benzoyl hydrazone (18) and N-(3-nitro)phenylsulfonyl-3-acetyl-6-methylindole benzoyl hydrazone (23) displayed the most potent anti-HIV-1 activity with EC50 values of 0.26 and 0.31 µg/mL, and TI values of >769.23 and >645.16, respectively. It is noteworthy that introduction of R3 as the methyl group and R2 as the hydrogen group could result in more potent compounds. This suggested that introduction of R3 as the methyl group could be taken into account for further preparation of these kinds of compounds as anti-HIV-1 agents