scholarly journals Synthesis, Crystal Structure and Biological Evaluation of Novel 2-Phenylthiazole Derivatives as Butyrylcholinesterase Inhibitors

2018 ◽  
Vol 42 (7) ◽  
pp. 366-370 ◽  
Author(s):  
Da-Hua Shi ◽  
Xiao-Dong Ma ◽  
Yu-Wei Liu ◽  
Wei Min ◽  
Fu-Jun Yin ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Docking Study ◽  
Biological Evaluation ◽  
Hirshfeld Surface ◽  
Inhibition Activity ◽  
X Ray Diffraction ◽  
Anionic Site ◽  
Crystal Lattices ◽  
X Ray ◽  
Crystal Structure Formation

To find novel butyrylcholinesterase inhibitors, three novel 2-phenylthiazole derivatives were synthesised. The synthesised compounds were characterised by NMR and single-crystal X-ray diffraction analysis. Hirshfeld surface analysis and two-dimensional fingerprint plots of the compounds were used as a theoretical approach to assess the driving force for crystal structure formation via the intermolecular interactions in the crystal lattices of the synthesised compounds. Among the three compounds, N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro- 1H-pyrazol-4-yl)-2-(4-methoxyphenyl)thiazole-4-carboxamide showed the best butyrylcholinesterase-inhibition activity with an IC50 value of 75.12 μM. A docking study demonstrated that this compound interacts with the peripheral anionic site of butyrylcholinesterase.

scholarly journals Synthesis, characterization, crystal structures, and the biological evaluation of 2-phenylthiazole derivatives as cholinesterase inhibitors

2020 ◽  
pp. 174751982097654
Author(s):  
Da-Hua Shi ◽  
Meng-qiu Song ◽  
Xiao-Dong Ma ◽  
Jia-Bin Su ◽  
Jing Wang ◽  
...  
Keyword(s):  
Cholinesterase Inhibitors ◽  
Docking Study ◽  
Biological Evaluation ◽  
Acetylcholinesterase Inhibition ◽  
Cholinesterase Inhibition ◽  
Resonance Spectroscopy ◽  
Inhibition Activity ◽  
X Ray Diffraction ◽  
Anionic Site ◽  
Ellman’S Method

Four 2-phenylthiazole derivatives are synthesized, characterized, and evaluated as cholinesterase inhibitors. The structures of the 2-phenylthiazole derivatives are confirmed by 1H and 13C nuclear magnetic resonance spectroscopy, single-crystal X-ray diffraction studies, and Hirshfeld surfaces analysis. Hirshfeld surface analysis of the prepared compounds showed C–H···O intermolecular interactions. The cholinesterase inhibition activities of the synthesized compounds are tested by Ellman’s method. [2-(4-Benzyloxyphenyl)-thiazol-4-yl]-(3,5-dimethylpiperidin-1-yl)-methanone showed the best acetylcholinesterase inhibition activity with an IC50 value of 8.86 µM and the best butyrylcholinesterase inhibition activity with an IC50 value of 1.03 µM. A docking study demonstrates that the same compound interacts with the catalytic anionic site and peripheral anionic site of acetylcholinesterase and the catalytic anionic site of butyrylcholinesterase.

Synthesis, Crystal Structure and Biological Evaluation of Novel 2-Phenylthiazole Derivatives as Multi-Targeting Agents to Treat Alzheimer's Disease

2017 ◽  
Vol 41 (9) ◽  
pp. 551-555 ◽  
Author(s):  
Da-Hua Shi ◽  
Zong-Ming Tang ◽  
Xiao-Dong Ma ◽  
Wei Min ◽  
Xiang-Jian Xu ◽  
...  
Keyword(s):  
Active Site ◽  
Docking Study ◽  
Biological Evaluation ◽  
Acetylcholinesterase Inhibition ◽  
Cholinesterase Inhibition ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
Anionic Site ◽  
X Ray ◽  
Catalytic Active Site

Three novel 2-phenylthiazole derivatives were synthesised and characterised by spectroscopic techniques. The structure of the synthesised compounds was unambiguously confirmed by a single-crystal X-ray diffraction analysis of ethyl 2-(4-{[5-(4-benzylpiperidin-1-yl)pentyl]oxy}phenyl)thiazole-4-carboxylate. All of the compounds presented good cholinesterase-inhibition activities and ethyl 2-(4-{[5-(4-benzylpiperidin-1-yl)pentyl]oxy}phenyl)thiazole-4-carboxylate showed the best acetylcholinesterase-inhibition and butyrylcholinesterase-inhibition abilities with IC50 values of 5.19 μM and 5.83 μM. The docking study demonstrated that it could interact with both the catalytic active site (CAS) and the peripheral anionic site (PAS) of acetylcholinesterase and could chelate with metal ions like Cu2+ and Zn2+.

Influence of fluorine side-group substitution on the crystal structure formation of benzene-1,3,5-trisamides

CrystEngComm ◽  
2014 ◽  
Vol 16 (39) ◽  
pp. 9273-9283 ◽  
Author(s):  
Christoph Zehe ◽  
Marko Schmidt ◽  
Renée Siegel ◽  
Klaus Kreger ◽  
Venita Daebel ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Nmr Spectroscopy ◽  
Structure Formation ◽  
Solid State Nmr ◽  
Quantum Chemical ◽  
Side Group ◽  
X Ray Diffraction ◽  
X Ray ◽  
Crystal Structure Formation

The crystal structure of 1,3,5-tris(2-fluoro-2-methylpropionylamino)benzene was solved by combining powder X-ray diffraction, solid-state NMR spectroscopy and quantum chemical calculations.

Crystallographic and computational studies of a new organoarsenate compound: o-anisidinium dihydroarsenate

2019 ◽  
Vol 75 (2) ◽  
pp. 128-134
Author(s):  
Ali Harchani ◽  
Damian Trzybiński ◽  
Sylwia Pawlędzio ◽  
Krzysztof Woźniak ◽  
Amor Haddad
Keyword(s):  
Crystal Structure ◽  
Solution Method ◽  
Theoretical Calculations ◽  
Hirshfeld Surface ◽  
Computational Studies ◽  
Supramolecular Architecture ◽  
X Ray Diffraction ◽  
Triclinic Space Group ◽  
X Ray ◽  
Electrophilic Reactivity

The crystal structure and the results of theoretical calculations for the new organoarsenate salt o-anisidinium dihydroarsenate (systematic name: 2-methoxyanilinium dihydrogen arsenate), C7H10NO+·H2AsO4 −, are reported. The salt, crystallizing in the triclinic space group P\overline{1}, was synthesized using a solution method and was characterized by single-crystal X-ray diffraction analysis. It possesses a layered supramolecular architecture in the crystal. The intermolecular interactions were studied using Hirshfeld surface analysis which confirmed that hydrogen bonds and H...H contacts play dominant roles in the crystal structure of the investigated system. An analysis of the electronic structure and molecular modelling using charge distribution confirms the good electrophilic reactivity of the title compound.

scholarly journals Pressure-induced polymorphism in cyclopropylamine

2005 ◽  
Vol 61 (6) ◽  
pp. 717-723 ◽  
Author(s):  
Patricia Lozano-Casal ◽  
David R. Allan ◽  
Simon Parsons
Keyword(s):  
Crystal Structure ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Amino Group ◽  
X Ray Diffraction ◽  
Orthorhombic Space Group ◽  
X Ray ◽  
Cell Dimensions ◽  
Graph Set ◽  
Unit Cell Dimensions

The crystal structure of cyclopropylamine at 1.2 GPa has been determined by X-ray diffraction methods. The structure of this phase is orthorhombic, space group Pbca and the unit-cell dimensions are a =  5.0741 (10), b  =  9.7594 (10) and c  =  13.305 (2) Å. Only one of the two H atoms of the amino group actively participates in the formation of the hydrogen-bonded chains, C(2) in graph-set notation, which lie parallel to the crystallographic a axis. Additionally, the topology of the crystal packing is studied using both Voronoi–Dirichlet polyhedra and Hirshfeld surface analyses for the low-temperature and the high-pressure structures of cyclopropylamine and the results are compared.

BODIPY trimer with 1,3,5-triazine core: Facile synthesis and crystal structure

2021 ◽  
pp. A-H
Author(s):  
Chunhua Huang ◽  
Bin Shen ◽  
Kaili Wang ◽  
Xiaofei Sun
Keyword(s):  
Crystal Structure ◽  
Fluorescence Spectroscopy ◽  
Hirshfeld Surface ◽  
Spectroscopic Methods ◽  
X Ray Diffraction ◽  
Facile Synthesis ◽  
Synthesis And Crystal Structure ◽  
X Ray ◽  
Design And Synthesis ◽  
H Nmr

Trimerization reaction of 8-(4[Formula: see text]-cyanophenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (CN-BODIPY) led to the isolation of a new triazine-based BODIPY trimer 2,4,6-tris(8[Formula: see text]-phenyl-1[Formula: see text],3[Formula: see text],5[Formula: see text],7[Formula: see text]-tetramethyl-4[Formula: see text],4[Formula: see text]-difluoro-4[Formula: see text]-bora-3a[Formula: see text],4a[Formula: see text]-diaza-s-indacene)-1,3,5-triazine (1). This BODIPY trimer 1 have been characterized by a series of spectroscopic methods including MALDI-TOF mass, 1H NMR, electronic absorption, IR and fluorescence spectroscopy. In particular, the single crystals of 1 have be obtained by slow diffusion of methanol into the solution of this compound in CHCl3. The BODIPY trimer structure of 1 with a triazine core has been directly revealed on the basis of single crystal X-ray diffraction analysis with the intermolecular interactions investigated by Hirshfeld surface analysis. This work will be helpful for the design and synthesis of new multiple BODIPY derivatives with various application.

A new ladder-type silver(I) coordination polymer with 4,4′-bipyridine and 4-[(4-carboxybenzyloxy)methyl]benzoate ligands: synthesis, crystal structure, fluorescence properties and Hirshfeld surface analysis

2020 ◽  
Vol 76 (10) ◽  
pp. 952-957
Author(s):  
Zhao Chen ◽  
Zilong Zhang ◽  
Chong Zhang ◽  
Yu Xiao
Keyword(s):  
Crystal Structure ◽  
Coordination Polymer ◽  
Surface Analysis ◽  
Silver Ions ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Fluorescence Properties ◽  
X Ray Diffraction ◽  
X Ray ◽  
Hydrothermal Methods

A novel ladder-type coordination polymer (CP), poly[(μ-4,4′-bipyridine-κ2 N:N′){μ-4-[(4-carboxybenzyloxy)methyl]benzoato-κO}silver(I)](Ag—Ag), [Ag(C16H13O5)(C10H8N2)] n or [Ag(HL)(4,4′-bpy)] n {H2 L is 4,4′-[oxybis(methylene)]dibenzoic acid and 4,4′-bpy is 4,4′-bipyridine}, was synthesized using hydrothermal methods. The complex was characterized by IR spectroscopy, elemental analysis and single-crystal X-ray diffraction, and is a ladder-type CP which exhibits an obvious Ag—Ag interaction. The legs of the ladder are formed by parallel 4,4′-bipy ligands and silver ions, and the rungs are constructed by Ag—Ag interactions. A Hirshfeld surface analysis was carried out and is discussed in detail. The complex also displays favourable fluorescence properties.

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