Search

An iodophor-catalyzed direct disulfenylation of amino naphthalenes with aryl sulfonyl hydrazines in water was developed. A series of aryl sulfides were obtained in moderate to excellent yields. The advantages of this green protocol were the simple reaction conditions (metal-free, water as the solvent, under air), the odorless and easily available sulfur reagent, the broad substrate scope, and gram-scale synthesis. Moreover, the potential application of aryl sulfides was exemplified by further transformations. [ABSTRACT FROM AUTHOR]

An iodophor-catalyzed direct disulfenylation of amino naphthalenes with aryl sulfonyl hydrazines in water was developed. A series of aryl sulfides were obtained in moderate to excellent yields. The advantages of this green protocol were the simple reaction conditions (metal-free, water as the solvent, under air), the odorless and easily available sulfur reagent, the broad substrate scope, and gram-scale synthesis. Moreover, the potential application of aryl sulfides was exemplified by further transformations.

In this current paper, fifteen novel sulfonyl hydrazone derivatives have been successfully synthesized and evaluated for antioxidant activity as well as their effects on inhibitory activity toward acetylcholinesterase (AChE). By using 1H NMR, 13C NMR, FT‐IR, and high‐resolution mass spectrometry methods, the full characterization data of the novel compounds were obtained. The synthesized compounds capacity to inhibition glucosidase and exhibit antioxidant activity were tested in vitro. It was determined that compounds (E)‐4‐((2‐((4‐chlorophenyl)sulfonyl)hydrazone)methyl)‐2‐methoxyphenylfuran‐2‐carboxylate (21), (E)‐2‐methoxy‐4‐((2‐(phenylsulfonyl)hydrazone)methyl)phenylfuran‐2‐carboxylate (17) and (E)‐4‐((2‐((4‐bromophenyl)sulfonyl)hydrazone)methyl)‐2‐methoxyphenylfuran‐2‐carboxylate (25) showed good antioxidant activity. Upon examining the acetylcholinesterase inhibitory activity, it was determined that compounds (E)‐2‐methoxy‐4‐((2‐((4‐methoxyphenyl)sulfonyl) hydrazone)methyl)phenylacetate (27) (10.39 μM), (E)‐4‐((2‐((4‐chloro phenyl)sulfonyl) hydrazone)methyl)‐2‐methoxyphenylfuran‐2‐carboxylate (21) (10.81 μM), (E)‐4‐((2‐((4‐chloro phenyl)sulfonyl)hydrazone)methyl)‐2‐methoxyphenyl thiophene‐2‐carboxylate (22) (12.92 μM) and (E)‐2‐methoxy‐4‐((2‐(phenylsulfonyl)hydrazone)methyl)phenylfuran‐2‐carboxylate (17) (12.93 μM) showed potent inhibitory effects. Molecular docking simulations were used to investigate the interactions of novel sulfonyl hydrazone derivatives with human acetylcholinesterase protein. The ligands exhibited strong binding to the receptor protein with potent inhibition. [ABSTRACT FROM AUTHOR]

In this work, a series of new sulfonyl hydrazones were synthesized and screened for antioxidant and anticholinesterase, tyrosinase and urease enzyme inhibition activities. In addition, molecular docking study was applied to better understand the inhibitory mechanism at the molecular level. Further, bioavailability of the synthesized compounds is considered in terms of the Lipinski rule and the design of their pharmacokinetic and pharmacodynamic properties is found reliable. In the AChE activity assay results, compound 8 was the most active one, while being less active than galantamine that was used as the standard drug. In the BChE activity testing of sulfonyl hydrazone derivatives (1–8), , compounds 3, 4, 5, 6, 7 and 8 were the most active drugs and showed much better activity than galantamine used as the standard. Compounds 8, 5 and 4 showed the best tyrosinase inhibitory activity with IC50 values of 9.75 ± 0.23, 13.18 ± 0.67 and 16.29 ± 0.73 mM, respectively. [ABSTRACT FROM AUTHOR]

A facile method for the synthesis of pyrazoles bearing novel N‐sulfonyl and 5‐alkylthio functional substructures has been developed via the reactions of ketene dithioacetals and sulfonyl hydrazines. The reactions are conducted with simple p‐toluenesulfonic acid (p‐TSA) promotion and mild heating under air atmosphere, leading to the synthesis of target products with highly diverse functional substitution. [ABSTRACT FROM AUTHOR]

Two new simple triphenylamine-based sulfonyl hydrazone derivatives DBBS ((E)- N '-(4-(diphenylamino)benzylidene)benzenesulfonohydrazide) and DBMS ((E)- N '-(4-(diphenylamino)benzylidene)-4-methylbenzenesulfonohydrazide) were designed and synthesized via one-step aldimine condensation reaction to investigate the influence of terminal methyl group on their photophysical, crystal stacking and mechanofluorochromic (MFC) properties. Interestingly, reversible multi-color fluorescence tuning and switching mechanofluorochromism was found for DBBS due to the nature of polymorphs, and DBMS exhibited reversible bicolor switching mechanofluorochromism. Additionally, the reversible MFC behavior was ascribed to the phase transition between the crystalline and amorphous states, which have been confirmed by powder X-ray diffraction (PXRD), field emission scanning electron microscopy (FESEM) and differential scanning calorimetry (DSC) results. The obtained results showed that terminal methyl group did not only regulate molecular conformations and/or intermolecular interactions in crystals, but also affect the force-stimuli responsiveness. The present study provided insight into the development of multicolor switching materials by rational modification of classic luminogens. [Display omitted] • Both compounds exhibited mechanofluorochromism. • Reversible multi-color fluorescence tuning and switching mechanofluorochromism was found for DBBS. • Terminal methyl group could regulate molecular conformations and/or intermolecular interactions. • Terminal methyl group also affected the force-stimuli responsiveness. [ABSTRACT FROM AUTHOR]