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1.
A series of halogenated 1,5-diarylimidazole compounds were synthesized and their inhibitory effects on LPS-induced PGE2 production in RAW 264.7 cells were evaluated. A wide variety of 2,4-, 4-, and 2-halogenated 5-aryl-1-(4-methylsulfonylphenyl)imidazoles were synthesized for SAR study via two different pathways. Overall, 4-halogenated 5-aryl-1-(4-methylsulfonylphenyl)imidazoles, regardless of the species of halogen, exhibited very strong inhibitory activities of PGE2 production. Among them, 4-chloro-5-(4-methoxyphenyl)-1-(4-methylsulfonylphenyl)imidazole (3, IC50 3.3 nM ± 2.93), and 4-chloro-5-(4-chlorophenyl)-1-(4-methylsulfonylphenyl)imidazole (13, IC50 5.3 nM ± 0.23) showed the best results.  相似文献   

2.
Four novel ON donor Schiff bases (E)-3-((4-phenoxyphenylimino)methyl)benzene-1,2-diol (HL1),(E)-3-((4-(4-biphenyloxy)phenyliminomethyl)benzene-1,2-diol (HL2), (E)-3-((4-naphthoxyphenylimino)methyl)benzene-1,2-diol (HL3), (E)-3-((4-(2-naphthoxy)phenylimino)methyl)benzene-1,2-diol (HL4) and their copper(II) complexes bis((E)-3-((4-phenoxyphenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L1)2) bis((E)-3-((4-(4-biphenyloxy)phenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L2)2), bis((E)-3-((4-naphthoxyphenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L3)2), bis((E)-3-((4-(2-naphthoxy)phenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L4)2) have been synthesized and characterized by spectroscopic (FTIR, NMR, UV–visible) and elemental analysis. The crystal structures of HL1, HL2, HL3, and HL4 have been determined, which reveal intramolecular N-H?O (HL1, HL2, HL3, and HL4) hydrogen bonds in the solid state. Keto-amine and enol-imine tautomerism is exhibited by the Schiff bases in solid and solution states. The Schiff bases and their copper(II) complexes have been screened for their biological activities. In antimicrobial assays (antibacterial and antifungal), HL4 showed promising results against all strains through dual inhibition property while the rest of the compounds showed activity against selective strains. On the other hand, in cytotoxic, DPPH, and inhibition of hydroxyl (OH) free radical-induced DNA damage assays, the results were found significantly correlated with each other, i.e. the ligands HL1 and HL2 showed moderate activity while their complexes Cu(L1)2 and Cu(L2)2 exhibited prominent increase in activity. As the results of these assays are supporting each other, it represents the strong positive correlation and antioxidant nature of investigated compounds.  相似文献   

3.
Two tetranuclear Ni(II) complexes: [Ni4(HL1)4] ⋅ H2O ( 1 ) and [Ni4(HL2)4] ⋅ 1.5 dmf ( 2 ) where dmf=dimethylformamide, H3L1=4-(tert-butyl)-2-(((2-hydroxy-5-nitrophenyl)imino)methyl)-6-(hydroxymethyl)phenol and H3L2=4-(tert-butyl)-2-(hydroxymethyl)-6-(((2-hydroxyphenyl)-imino)methyl)phenol, have been prepared and characterized by single crystal X-Ray diffraction, elemental analysis and FT-IR spectroscopy. The solid-state structures reveal the formation of highly symmetric and asymmetric [Ni4O4] cubane cores in complexes 1 and 2 , respectively. Extensive magnetic studies show that both complexes present ferromagnetic exchange interactions between the Ni(II) ions within the cubane core with g=2.113(3), J1=−7.89(8) cm−1, J2=13.3(1) cm−1 and |D|=11.3(4) cm−1 (for 1 ) and g=2.206(4), J1=1.0(1) cm−1, J2=7.8(1) cm−1 and |D|=8.7(2) cm−1 (for 2 ). The large anisotropy, high ground spin state (arising from the ferromagnetic coupling) and the good isolation of the clusters provided by the Schiff base ligands, give rise to the first examples of field-induced single-molecule magnets (FI−SMM) in Ni4O4 clusters and to the highest energy barrier reported to date in a Ni4O4 cluster.  相似文献   

4.
The following oligosaccharide sequences containing the repeating unit of the O-specific chain of lipopolysaccharides from aeromonas salmonicida have been synthesized: α-D-Glcp-(1→3)-α-L-Rhap-(1 →3)-β-D-ManpNAcO(CH2)8CO2Me, α-D-Glcp-(1 →4)-α-D-Glcp-(1→3)-α-L-Rhap-(1→3)-β-D-ManpNAcO(CH2)8CO2Me and α-D-Glcp(1→4)-α-D-Glcp-(1→3)-[β-D-ManpNAc(1→4)]-L-Rha.  相似文献   

5.
The 4-hydrazinobenzyl alcohol ( 3 was prepared (58%)) by diiobutylaluminiumhydride reduction of methyl 4-hydrazinobenzoate ( 4 ), whereas LiA1H4 or LiBh4 reduction of 4 proceeded further to yield (via intermediate 3 ) (4-tolyl)hydrazine ( 5 ). The alcohol 3 was stable under O2-free conditions and exhibited no tendency to eliminate H2O, neither thermally nor with H+ catalysis. Oxidation of 3 with SeO2 yielded 4-(hydroxymethyl)benzine-diazonium ion ( 8 ), identified by its azo coupling product 9 with 2-naphthol. Condensation of 3 with 1-benzyl 5-Hydrogen N-(benzyloxycarbonyl)-L-glutamate ( 10 ) in presence of dicyclohexylcarbodiimide afforded 81% of N2-(benzyloxycarbonyl)-L- glutamic acid 1-(benzyl-ester) 5-{2-[4-(hydroxymethyl)phenyl]hydrazide} ( 11 ) which upon controlled hydrogenolysis (quinoline-sulfur-poisoned Pd/C catalyst) gave 82% of L-Glutamic acid 5-{2-[4-(hydroxymethyl)phenyl] hydrazide} ( 1 ), i. e. agaritine, a metabolite of Agaricus bisporus. Without poisoning of the catalyst, hydrogenolysis of ( 11 ) yielded L-glutamic acid 5-[2-(4-tolyl)hydrazide] ( 12 ).  相似文献   

6.
(1S,4R)-7,7-Dimethyl-1-vinylbicyclo[2.2.1]heptan-2-one oxime in the system (CF3CO)2O-CF3COOH and (1S,4R)-1-(1,2-dibromoethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one in the system MeONa-MeOH undergo fragmentation to give exo-alkylidenecyclopentane derivatives, (4R)-4-cyanomethyl-5,5-dimethyl-1-[(1E)-trifluoroacetoxyethylidene]cyclopentane and isomeric (4R)-4-carboxymethyl-1-[(1ZE)-2-methoxyethylidene]-5,5-dimethylcyclopentanes, respectively. The trifluoroacetate derivative undergoes unusual rearrangement, yielding an equilibrium mixture of two isomers with endo- and exocyclic double bond.  相似文献   

7.
Six organic–inorganic complexes derived from bis-imidazole derivatives ([(H2L1)(CdCl3 ? H2O)2] (1), L1 = 1-(3-(1H-benzimidazol-1-yl)propyl)-1H-benzimidazole; [(H2L2)CdCl4] (2), L2 = 1,1′-bis(benzimidazolyl)methane; [(H2L3)CdCl4] (3), L3 = 1-(2-(1H-benzimidazol-1-yl)ethyl)-1H-benzimidazole; [(H2L4)4(CdCl4)4] ? 13H2O (4), L4 = 1,5-bis(1-benzimidazolyl)-3-oxapentane; [(H2L5)CdCl4] (5), L5 = 1-(4-(1H-benzimidazol-1-yl)butyl)-1H-benzimidazole; [(H2L6)(Cd2Cl8)0.5] ? H2O (6), L6 = 3,6-bis(imidazol-1-yl)pyridazine), and cadmium(II) chloride dihydrate were prepared and characterized by IR, X-ray structure analysis, elemental analysis, and TG analysis. The imidazolyl moieties in all six compounds are essentially planar. X-ray diffraction analysis revealed that complexes 1–6 have 3-D network structures built from hydrogen bonds between imidazolium cations, chlorocadmate anions, and water. The arrangements of the anions and cations in their solid state are dominated not only by the size and symmetry of the imidazolium cations, but also by the different structure types of the chlorocadmate anions as well as the hydrogen-bonded interactions existing in the crystal structures. All of the complexes are thermally stable.  相似文献   

8.
Acetylation of 2-(1-naphthyl) thiophene with acetyl chloride in the presence of SnCl4, or with acetic anhydride in the presence of H3PO4 gives 5-aceto-2-(1-naphthyl) thiophene. 5-Ethyl-2-[1-(3, 4-dihydronaphthyl)] thiophene, 5-ethyl-2-(1-naphthyl) thiophene and 3, 4-diacetoxymercuri-5-ethyl-2-(1-naphthyl) thiophene are now synthesized and characterized.  相似文献   

9.
Bis(1-(4-tolyl)-carboran-2-yl)-(4-tolyl)-borane [(1-(4-MeC6H4)-closo-1,2-C2B10H10-2-)2(4-MeC6H4)B] ( 1 ), a new bis(o-carboranyl)-(R)-borane was synthesised by lithiation of the o-carboranyl precursor and subsequent salt metathesis reaction with (4-tolyl)BBr2. Cyclic voltammetry experiments on 1 show multiple distinct reduction events with a one-electron first reduction. In a selective reduction experiment the corresponding paramagnetic radical anion 1.− was isolated and characterized. Single-crystal structure analyses allow an in-depth comparison of 1 , 1.− , their calculated geometries, and the S1 excited state of 1 . Photophysical studies of 1 show a charge transfer (CT) emission with low quantum yield in solution but a strong increase in the solid state. TD-DFT calculations were used to identify transition-relevant orbitals.  相似文献   

10.
2, 4-Bis-(4-methoxyphenyl)-1, 3, 2, 4-dithiadiphosphetane-2, 4-disulfide [Lawesson reagent (LR)] 1 reacts with p-quinone monoimine- 2a to give the novel benzo-1,3,2-oxathiaphosphol-5-(methanesulfonamido)-2-(4-methoxyphenyl)-2-sulfide 4 . On the other hand, the reaction of 2b and 3 with LR 1 leads to the formation of the benzo- and the naphtho-1,3,2-dithiaphosphol-5 -(benzenesulfonamido)- 2- (4-methoxyphenyl) -2-sulfide 5 , 6 . Thiation of 2a , 2b , and 3 with P4S10 yields phenoxathiin derivatives 8a , 8b , and 9 , respectively. The identity of the new products is established from analytical and spectroscopic evidence.  相似文献   

11.
The synthesis of 1-(4-hydroxyphenyl)-2-(2-fluoro-4-hydroxyphenyl)ethane ( FBPE ), 1-(4-hydroxyphenyl)-2-(2-chloro-4-hydroxyphenyl)ethane ( CIBPE ), 1-(4-hydroxyphenyl)-2-(2-bromo-4-hydroxyphenyl)ethane ( BrBPE ), and 1-(4-hydroxyphenyl)-2-(2-trifluoromethyl-4-hydroxyphenyl)ethane ( CF3BPE ), of the corresponding polymers based on 1,5-dibromopentane ( RBPE-5) , 1,8-dibromooctane ( RBPE-8 ), and of the copolymers based on various ratios of 1,5-dibromopentane and 1,8-dibromooctane [ RBPE-5/8(A/B )] is described. The phase transition temperatures and thermodynamic parameters of RBPE-5 and RBPE-8 polymers were compared to those of the corresponding polyethers based on 1,2-bis(4-hydroxyphenyl)ethane ( BPE ) and 1-(4-hydroxyphenyl)-2-(2-methyl-4-hydroxyphenyl)ethane ( MBPE ) which were reported previously. Both isotropic-nematic transition temperatures and corresponding thermodynamic parameters (i.e., enthalpy and entropy changes) decrease in the following order of the substituent R: H > F > CH3 > Cl > Br > CF3. This order corresponds to the increase of the breadth of the RBPE molecules, and agrees with the similar trends observed in low molar mass liquid crystals.  相似文献   

12.
5-Arylidene derivatives of rhodanine show various biological activities. The new crystal structures of five derivatives investigated towards ABCB1 efflux pump modulation are reported, namely, 2-[5-([1,1′-biphenyl]-4-ylmethylidene]-4-oxo-2-thioxothiazolidin-3-yl)acetic acid dimethyl sulfoxide monosolvate, C18H13NO3S2·C2H6OS ( 1 ), 4-[5-([1,1′-biphenyl]-4-ylmethylidene]-4-oxo-2-thioxothiazolidin-3-yl)butanoic acid, C20H17NO3S2 ( 2 ), 5-[4-(benzyloxy)benzylidene]-2-thioxothiazolidin-4-one, C17H13NO2S2 ( 3 ), 4-{5-[4-(benzyloxy)benzylidene]-4-oxo-2-thioxothiazolidin-3-yl}butanoic acid, C21H19NO4S2 ( 4 ), and 5-[4-(diphenylamino)benzylidene]-2-thioxothiazolidin-4-one, C22H16N2OS2 ( 5 ). Compounds 1 and 3 – 5 crystallize in the triclinic space group P, while 2 crystallizes in the monoclinic space group P21/n, where the biphenyl moiety is observed in two positions (A and B). Two molecules are present in the asymmetric unit of 5 and, for the other four compounds, there is only one molecule; moreover, 1 crystallizes with one dimethyl sulfoxide molecule. The packing of the molecules containing a carboxyl group ( 1 , 2 and 4 ) is determined by O—H…O hydrogen bonds, while in the other two compounds ( 3 and 5 ), the packing is determined by N—H…O hydrogen bonds. Additionally, induced-fit docking studies have been performed for the active compounds to investigate their putative binding mode inside the human glycoprotein P (P-gp) binding pocket.  相似文献   

13.
Chalcone-derived 3-phenyl-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCTPh) (1), 3-(4-chlorophenyl)-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4ClPh) (2), 3-(4-bromophenyl)-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4BrPh) (3), and 3-(4-nitrophenyl-1-pyridin-2-ylprop-2-en-1-one thiosemicarbazone (HPyCT4NO2Ph) (4) were obtained as well as their gallium(III) and zinc(II) complexes [Ga(PyCTPh)2]NO3 (Ga1), [Ga(PyCT4ClPh)2]NO3 (Ga2), [Ga(PyCT4BrPh)2]NO3 (Ga3), [Ga(PyCT4NO2Ph)2]NO3 (Ga4), [Zn(PyCTPh)2] (Zn1), [Zn(PyCT4ClPh)2] (Zn2), [Zn(PyCT4BrPh)2] (Zn3), and [Zn(PyCT4NO2Ph)2] (Zn4). The chalcones, thiosemicarbazones, and zinc(II) complexes were not active against Pseudomonas aeruginosa. The thiosemicarbazones proved to be more active than the parent chalcones against Staphylococcus aureus and Candida albicans. Coordination to zinc(II) resulted in activity improvement of most thiosemicarbazones against S. aureus. Coordination to gallium(III) significantly improved the antimicrobial activity of all thiosemicarbazones against the studied micro-organisms, suggesting this to be an effective strategy for antimicrobial activity enhancement.  相似文献   

14.
The reactions of octachlorocyclotetraphosphazatetraene, N4P4Cl8 (1) with difunctional aliphatic reagent, HO-(CH2)5-OH (3) have aroused a good deal of attention, and four types of products have been realized: one 2-open chain-(1′-oxy-5′-hidroxy-pentane)-2,4,4,6,6,8,8-heptachlorocylotetraphosphazatetraene, N4P4Cl7[O(CH2)5OH] (4); one 2,2-mono-spiro-(1′,5′-pentanedioxy)-4,4,6,6,8,8-hexachlorocyclotetraphosphazatetraene, N4P4Cl6[O(CH2)5O] (5); its isomers 2,4-mono-ansa-((1′,5′-pentanedioxy)-2,4,6,6,8,8- hexachlorocyclotetraphosphazatetraene (6) and 2,6-mono-ansa-(1′,5′-pentanedioxy)-2,4,6,6,8,8-hexachlorocyclotetraphosphazatetraene (7); one 2,2,6,6-dispiro-(1′,5′-pentanedioxy)-4,4,8,8-tetrachlorocyclo- tetraphosphazatetraene, N4P4Cl4[O(CH2)5O]2 (8); two isomeric 2,4,6,8-bisansa-(1′,5′-pentanedioxy)-2,4,6,8-tetrachlorocyclotetraphosphazatetraene (9) and 2,6,4,8-bisansa-(1′,5′-pentanedioxy)-2,4,6,8-tetrachloro-cyclotetraphosphazatetraene (10); one 4,4,8,8-dispiro-2,6-ansa- (1′,5′-pentanedioxy)-2,6-dichlorocyclotetra-phosphazatetraene, N4P4Cl2[O(CH2)5O]3 (11), one 2,2,4,4,6,6-trispiro-(1′,5′-pentanedioxy)-8,8-dichlorocyclo-tetraphosphazatetraene, N4P4Cl2[O(CH2)5O]3 (12); and a 2,2,4,4,6,6,8,8-tetraspiro-(1′,5′-pentanedioxy)-cyclotetraphosphazatetraene derivative, N4P4[O(CH2)5O]4, (13). The respective structures were deduced by means of elemental analysis, mass spectrum, and 31P, 1H, and 13C nuclear magnetic resonance spectroscopic investigations.  相似文献   

15.
The 1-β-D-ribofuranosides of 2-keto-4-(N-methoxyamino)pyrimidine, 2-keto-4-(N-methyl-N-methoxyamino)pyrimidine, and 2-keto-3-methyl-4-(N-methoxyamino)pyrimidine were synthesized, and their pKa values were determined by spectrophotometry. The pKa values of the compounds are evidence that the tautomeric equilibrium between the oxime and hydroxyamine forms of 1-β-D-ribofuranosyl-2-keto-4-(N-methoxyamino)pyrimidine in aqueous solutions is shifted to favor the oxime form (KT?25).  相似文献   

16.
Six salts, ([(H2L1)(ZnCl4)] (1) (L1 = 1,1′-bis(benzimidazolyl)methane), [(H2L1)(CuCl4)]·H2O (2), [(H2L2)(ZnCl4)] (3) (L2 = 1-(3-(1H-benzimidazol-1-yl)propyl)-1H-benzimidazole), [( H2L2)(CuCl4)] (4), [(H2L3)(CuCl4)]·H2O (5) (L3 = 1- (4-(1H-benzimidazol-1-yl)butyl)-1H-benzimidazole), and [(H2L4)(ZnCl4)]·H2O (6) (L4 = 3,6-bis(imidazol-1-yl)pyridazine)), derived from bis(benzimidazole)/bis(imidazole) and metal(II) chloride dihydrate (zinc(II) chloride and copper(II) chloride dihydrate) were prepared and characterized by IR, X-ray structure analysis, elemental analysis, and TG analysis. The aromatic rings of the cations in all of the compounds are planar. X-ray diffraction analysis revealed that all the complexes have 3-D layer network structures built from hydrogen bonds between the cations and chlorometallate anions. Water molecules also play an important role in structure extension in 2, 5, and 6. The arrangements of the anions and cations in their solid state are dominated not only by size and symmetry of the cations, but also by the non-covalent interactions existing in the crystal structures.  相似文献   

17.
The synthesis, crystal structures, and luminescent properties of two new complexes containing tetrazolyl ligands are described. Refluxing a mixture of fipronil (fipronil = (±)-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile), sodium azide, and CuCl2 in ethanol and water gives complex 1, [M(L)2](H2O)2] ? 2H2O (HL = (±)-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-tetrazole, M = Cu). Hydrothermal reaction of fipronil, sodium azide, and Cd(ClO4)2 in the presence of water and ethanol (Demko–Sharpless tetrazole synthesis) yields 2, [M(L)2](H2O)2] ? 2H2O (M = Cd). The metals in both complexes are six coordinate from two water molecules, two nitrogens from different tetrazolyl groups, and two nitrogens from pyrazolyl groups. Photoluminescence studies reveal that 2 exhibits strong blue fluorescent emission at λ max = 451 nm in solid state at room temperature.  相似文献   

18.
Bromination of (E)-1-[4-(2-carboxy-vinyl)phenyl]-[1,2,3]triazole-4-carboxylic acid ethyl ester, which was synthesized in 90% yield by a Huisgen-type [3 + 2]-cycloaddition reaction between 3-(4-azidophenyl) acrylic acid and ethyl propiolate, in CHCl3 followed by a debrominative decarboxylation reaction with Et3N in DMF under microwave irradiation condition afforded stereoselective (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in 94% yield. Treatment of (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester with EtONa in DMF afforded 1-(4-ethynylphenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in a yield of 90%.  相似文献   

19.
Four new complexes, Cu2(p-2-bmb)2Cl4 (1), Cu2(p-2-bmb)2Br4 (2), Zn2(p-3-bmb)2Cl4 (3), and [Cu3(p-3-bmb)2Cl4·(CH3OH)2] n (4), have been synthesized under solvothermal reactions based on V-shaped flexible ligands 1-((2-(pyridin-2-yl)-1H-benzoimidazol-1-yl)methyl)-1Hbenzotriazole (p-2-bmb) and 1-((2-(pyridin-3-yl)-1H-benzoimidazol-1-yl)methyl)-1Hbenzotriazole (p-3-bmb). Complexes 1–3 are binuclear, whereas 4 is an infinite chain with trimetallic units, and then these complexes are further extended into 3D supramolecular architectures by ππ interactions and hydrogen bonds. In vitro antitumor activities of these complexes on four human tumor cell lines (gastric tumor cell line, esophagus tumor cell line, liver tumor cell line, colon tumor cell line) were evaluated by MTT assay. The results exhibit that these complexes inhibit the growth of cancer cells by inducing apoptosis, and the inhibition effect shows time- and dose-effect relationship.  相似文献   

20.
采用(E)-4-(4-(diphenylamino)styryl)-1-methylpyridinium iodide(DPASPI,DPASP=(E)-4-(4-(diphenylamino)styryl)-1-methylpyridi-nium),设计合成2种新型有机-无机杂化物(DPASP)2[Zn(NCS)4]·2CH3OH(1)和{(DPASP)2[Cd(SCN)(NCS)3]·2CH3OH}n2)。通过单晶X射线衍射进行了表征,结果表明杂化物12是由有机吡啶阳离子和异硫氰酸金属配阴离子组成的,具有不同空间结构。通过1H NMR谱图解释了离子间相互作用。对具有高量子产率的杂化物12的红光发光性质进行了研究。  相似文献   

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