氯代苯二酚双苯醚的合成与抑菌活性研究

为了寻求优良的苯醚类新化合物抑菌剂,本文设计合成了邻(对)苯二酚二-(2-氯-4-羟基苯基)醚,其结构均经1HNMR、IR、MS和元素分析证实,并且测试了化合物对大肠杆菌,金黄色葡萄球菌,白色念珠菌,白色葡萄球菌,变形杆菌,卡他双球菌,青枯假单胞菌的抑菌活性,初步研究结果表明:羟基的位置对活性存在较大影响,羟基的个数对试剂的抑菌活性没有明显的影响。     

Synthesis,characterization, and biological evaluation of new copper complexes of naphthyl pyrazole ligands

Two naphthalene pyrazole ligands were synthesized using KOH/DMSO and Cu catalyst and characterized with FT-IR, ESI-MS, ¹H, and ¹³C NMR spectroscopies. The crystal structures of 1-(2-methylnaphthalen-1-yl)-1H-pyrazole (MeNap-Pz) ligand have been determined with X-ray crystal structure analysis. Reaction of the ligands with Cu(NO₃)₂x3.5H₂O gave two new complexes and characterized with magnetic susceptibility, molar conductance, FT-IR, LCMS-MS, ICP-OES, NMR, thermogravimetric analysis, and ESR spectra. The spectral data of the ligands are coordinated to the metal ion through the nitrogen atoms of the pyrazole ring. Consequently, it has been determined that [Cu(MeNap-Pz)₂(NO₃)]NO₃.2H₂O complex showed square planar geometry and [Cu(NapMe-Pz)₂(NO₃)₂].H₂O complex showed octahedral geometry. All compounds were screened for in vitro antibacterial activity and copper complexes have been shown to be effective on bacteria.     

Antimicrobial activity on the copolymers of 2,4‐dichlorophenyl methacrylate with methyl methacrylate: Synthesis and characterization

Copolymers of monomers 2,4‐dichlorophenyl methacrylate (2,4‐DMA) and methyl methacrylate (MMA) were synthesized with different monomer feed ratios using toluene as a solvent and 2,2′‐azobisisobutyronitrile (AIBN) as an initiator at 70 °C. The copolymers were characterized by IR‐spectroscopy, and copolymer composition was determined with UV‐spectroscopy. The linearization method of Fineman–Ross was employed to obtain the monomer reactivity ratios. The molecular weights and polydispersity indexes were determined by gel permeation chromatography (GPC). Thermogravimetric analyses of polymers were carried out in nitrogen atmosphere. The homo‐ and copolymers were tested for their antimicrobial properties against selected microorganisms. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 5227–5234, 2004     

Synthesis,characterization, crystal structure,and antimicrobial studies of novel thiourea derivative ligands and their platinum complexes

N,N-Di-R-N′-(4-chlorobenzoyl)thiourea (Di-R: diethyl, di-n-propyl, di-n-butyl and diphenyl) ligands (HL^1–4) and their Pt(II) complexes (cis-[Pt(L^1–4-S,O)₂]) have been synthesized and structurally characterized by elemental analyses, FT-IR and NMR spectroscopy. HL² ligand and cis-[Pt(L⁴-S,O)₂] metal complex have been also characterized by a single-crystal X-ray diffraction study. HL², C₁₄H₁₉ClN₂OS, crystallizes in the monoclinic space group P2₁/n (no. 14), with Z = 4, and unit cell parameters, a = 11.1405(16) Å, b = 9.7015(12) Å, c = 14.790(2) Å, β = 106.547(7)°. The cis-[Pt(L⁴-S,O)₂], C₄₀H₂₈Cl₂N₄O₂PtS₂: triclinic, space group P-1 (no. 2), a = 8.9919(3) Å, b = 14.7159(6) Å, c = 15.7954(6) Å, α = 113.9317(18)°, β = 97.4490(18)°, and γ = 105.0492(16)°. Single crystal analysis of complex, cis-[Pt(L^1–4-S,O)₂], revealed that a square planar coordination geometry is formed around the platinum atom by two sulfur and two oxygen atoms of the related ligands, which are in a cis configuration. In addition, the thiourea derivative ligands and their complexes were evaluated for both their in-vitro antibacterial and antifungal activity. The results have been reported, explained, and compared with fluconazole and ampicillin, used as reference drugs.     

Synthesis and antimicrobial activity evaluation of new dithiocarbamate derivatives bearing thiazole/benzothiazole rings

The synthesis of 2-(substituted phenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A1-A24) derivatives and 2-(4-substituted thiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B1-B14) derivatives was undertaken starting from the potassium salt of 4-(2-pyrimidinyl)piperazine dithiocarbamate. The structures of the obtained compounds were elucidated by ¹H NMR, ¹³C NMR, MS spectral data, and elemental analysis. The antimicrobial activity of the thirty eight newly synthesized compounds were tested against 12 microorganism strains using the microdilution technique. Compounds 2-(4-ethoxycarbonylthiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B12), 2-(3-fluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A18) and 2-(3,4-difluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A21) were determined to possess high antimicrobial activity.     

Synthesis,characterization and antimicrobial study via new heterocyclic derivatives of trimethoprim

New compounds of trimethoprim heterocyclic derivatives were synthesized. These compounds were synthesized through the condensation reaction between trimethoprim with bromoacetic acid to yield compound 1. Several Schiff bases 2–7 have been synthesized by the condensation different aromatic aldehydes with compound 1. Compound 8 were formed from the reaction of sodium nitrite and acetyl acetone in presence of conc. hydrogen chloride to obtain the hydrazono derivative; then, Cyclocondensation of compound 8 with hydrazine hydrate, phenyl hydrazine and dinitrophenyl hydrazine respectively to yield compounds 9–11 in ethanol affording the pyrazoline derivatives. This work involves the synthesis of some 1,2,3-Triazoles derived from compound 1 by the action of sodium azide on the diazonium chloride salt to yield 5-azido-8-(3,4,5-trimethoxybenzyl)imidazo[1,2-c]pyrimidin-3(2H)-one 12. Finally, by reaction of 12 with acetyl acetone and ethyacetoacetate; respectively in sodium ethoxide/ethanol as a solvent to form compounds 13, 14. The structures of the compounds 1–14 were characterized by elemental analysis, spectral data and antimicrobial evaluation of the some newly synthesized compounds and found that the synthesized compounds are active against tested Gram positive and Gram negative bacteria like Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Proteus.     

Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies

A new series of transition metal complexes of Cu(II), Ni(II), Co(II), Mn(II), Zn(II), VO(IV), Hg(II) and Cd(II) have been synthesized from the Schiff base (L) derived from 4-aminoantipyrine, 3-hydroxy-4-nitrobenzaldehyde and o-phenylenediamine. Structural features were obtained from their elemental analyses, magnetic susceptibility, molar conductance, mass, IR, UV-Vis, ¹H NMR and ESR spectral studies. The data show that these complexes have composition of ML type. The UV-Vis, magnetic susceptibility and ESR spectral data of the complexes suggest a square-planar geometry around the central metal ion except VO(IV) complex which has square-pyramidal geometry. The redox behaviour of copper and vanadyl complexes was studied by cyclic voltammetry. Antimicrobial screening tests gave good results in the presence of metal ion in the ligand system. The nuclease activity of the above metal complexes shows that Cu, Ni and Co complexes cleave DNA through redox chemistry whereas other complexes are not effective.     

Synthesis,characterization and antimicrobial activity of a bidentate NS Schiff base of S-benzyl dithiocarbazate and its divalent complexes

The reaction of S-benzyl dithiocarbazate (SBDTC) with 2,4,5-trimethoxybenzaldehyde afforded a bidentate NS Schiff base 1 (benzyl-3-N-(2,4,5-trimethoxyphenylmethylenehydrazine carbodithioate), which on further reaction with M(II) (where M(II) = nickel(II), zinc(II), palladium(II) and copper(II)) in ethanol under reflux yielded bis-chelated inner complexes [ML₂] 2–5 with deprotonated L. The ligand and its complexes were characterized by physicochemical techniques, viz., molar conductance, magnetic susceptibility measurement, IR, NMR, UV–Vis and mass spectroscopic techniques. The crystal structures of 1 and 5 were also determined by single-crystal X-ray crystallography. The crystal structure analysis showed that the ligand exists in its thione tautomeric form. In the complexes, each of the two deprotonated ligands chelated the metal ions through the β-nitrogen and the thione sulfur forming five-membered rings. The copper(II) complex (5) exhibited a square-planar geometry, where the two N₂S₂ chromophores are arranged trans. All the compounds showed strong antibacterial activity against S.-β-hemolyticus, Klebsiella pneumoni, and Escherichia coli. The compounds also showed strong antifungal activity against Aspergillus fumigatus, Aspergillus niger, Aspergillus flavus, and Candida albicans with the exception of the palladium(II) complex (4) which showed no activity, while all the compounds showed no activity against Fusarium vasinfectum.     

Synthesis and characterization of new thiosemicarbazonato molybdenum(VI) complexes and their in vitro antimicrobial activities

Abstract

Eight new mixed ligand complexes of dioxomolybdenum(VI) with 2-hydroxy-3-methoxy/3,5-dibromo benzaldehyde 4-phenyl/ethyl-S-methyl/butyl thiosemicarbazones (L) were synthesized. The complexes of general formula [MoO₂LD] (D: methanol, pyridine) were characterized by elemental analysis, IR, UV, and ¹H-NMR spectroscopy. The structure of 3a was also determined by X-ray single-crystal diffraction. The thiosemicarbazone ligands are coordinated to dioxomolybdenum(VI) center through ONN set and the sixth coordinated site of the molybdenum is occupied by the second ligand (D). The in vitro antimicrobial activities of all thiosemicarbazones and their dioxomolybdenum(VI) complexes were tested against Candida albicans, Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus.     

Synthesis,characterization, and antimicrobial activity of two Schiff base silver(I) complexes derived from 4-carboxybenzaldehyde

Two new Schiff base silver(I) complexes, {[Ag(L¹)][H₂O]}_∞ (1) and {[Ag(L²)][H₂O]}_∞ (2), where L¹ = 4-((2-diethylaminoethylimino)methyl)phenecarboxylate and L² = 4-([3-(morpholin-4-yl)propyl]iminomethyl)phenecarboxylate, have been synthesized and characterized. X-ray crystallographic analysis reveals that silver ions in 1 are bridged by L¹ to form a one-dimensional zigzag chain, while three silver ions in 2 are linked by L² to produce a two-dimensional coordination polymer. Guest water molecules in 1 generate a one-dimensional hydrogen-bonded chain. Both 1 and 2 offer high antibacterial activity against Gram-positive bacteria Staphylococcus aureus with MIC values of 0.26 and 0.24 mM and to exhibit good inhibitory activity against urease with the respective IC₅₀ values of 3.5 ± 0.1 and 3.8 ± 0.2 μM.     

Thermal behavior of some N,N-dimethylbiguanide derivatives displaying antimicrobial activity

N,N-Dimethylbiguanide derivatives (HDMBG)X, where X=CH₃COO (1), Cl (2) and NO₃ (3) respectively, exhibit in vitro antimicrobial activity on representative bacterial and fungal strains. The presence of N,N-dimethylbiguanidium ion for all derivatives was evidenced by IR and ¹H NMR spectra. Thermal analysis gave information on their decomposition steps and also on the accompanying thermodynamic effects. According to TG and DTG curves processes as melting, oxidative degradation as well as oxidative condensation of –C=N– units occur. The different nature of the anions results different melting points. Paracyanide formation at various condensation degrees was observed.     

Synthesis,characterization and antimicrobial activity of novel sulphapiperazine containing arylazopyrazoles

Mannich reaction of benzotriazole (1), ethyl-4-amino benzoate (2) and formaldehyde in ethanol afforded 4-(1H)-benzotriazoyl methyl amino benzoate (3), which on treatment with hydrazine hydrate results in the 4-(1H)-benzotriazoyl methyl amino benzoyl hydrazide (4). This compound on condensation with pre-prepared various ethyl-2-substituted phenyl hydrazono-3-oxobutyrates (6a–h), furnished 1-(4-((1H-benzo[d][1,2,3]triazol-1-yl) methyl amino) benzoyl)-3-methyl-4-(2-(4-(4-alkylpiperazin-1-ylsulfonyl) phenyl) hydrazono)-1H-pyrazol-5(4H)-ones (7a–h). All these compounds (7a–h) were characterized by spectral studies. The compounds showed significant antimicrobial activity against various bacteria and fungi.     

Synthesis,characterization, molecular docking studies and in vitro screening of new metal complexes with Schiff base as antimicrobial and antiproliferative agents

A series of Cu(II), Co(II), Pd(II), Pt(II), Zn(II), Cd(II) and Fe(III) complexes were designed and synthesized using Schiff base 1‐phenyl‐2,3‐dimethyl‐4‐(N‐3‐formyl‐6‐methylchromone)‐3‐pyrazolin‐5‐one (HL). The new metal complexes were investigated using various physicochemical techniques including elemental and thermal analyses, molar electric conductivity and magnetic susceptibility measurements, as well as spectroscopic methods. Also, the crystal structures of ligand HL and the Pd(II) complex were determined using single‐crystal X‐ray diffraction analysis. For all compounds, the antimicrobial activity was studied against a series of standard strains: Staphylococcus aureus, Bacillus cereus, Enterococcus faecalis, Escherichia coli, Acinetobacter baumannii, Candida albicans, Candida krusei and Cryptococcus neoformans. The in vitro antiproliferative activity of the ligand and complexes was evaluated against ten cancer cell lines: MSC, A375, B16 4A5, HT‐29, MCF‐7, HEp‐2, BxPC‐3, RD, MDCK and L20B. At 10 μM concentration a significant cytotoxic effect of the Co(II), Pd(II) and Cd(II) complexes was observed against B16 4A5 murine melanoma cells. The Zn(II) complex is active against HEp‐2, RD and MDCK cancer cell lines, where IC₅₀ values vary between 1.0 and 77.6 and for BxPC‐3 the activity index versus doxorubicin is 3.7 times higher.     

Synthesis,characterization and antimicrobial activity of zinc(II) ibuprofen complexes with nitrogen-based ligands

Metal carboxylate complexes possess different carboxylate coordination modes, e.g. monodentate, bidentate, and bridging bidentate. Five Zn(II) complexes were prepared and characterized in order to examine their coordination modes in addition to their biological activity. The syntheses were started by preparation of [Zn(ibup)₂(H₂O)₂] (1). Then, different nitrogen-donor ligands reacted with 1 to produce [Zn(ibup)₂(2-ampy)₂] (2), [Zn(ibup)(2-ammethylpy)] (3), [Zn(ibup)(2,2′-bipy)] (4), and [Zn₂(ibup)₄(2-methylampy)₂] (5) (ibup = ibuprofen, 2-ampy = 2-aminopyridine, 2-ammethylpy = 2-aminomethylpyridine, 2,2′-bipy = 2,2′-bipyridine, 2-methylampy = 2-(methylamino)pyridine). IR, ¹H NMR, ¹³C{¹H}-NMR and UV–vis spectroscopies were used for characterization. The crystal structures of 2 and 5 were determined by single-crystal X-ray diffraction. Investigation of in vitro antibacterial activities for the complexes against Gram-positive (Micrococcus luteus, Staphylococcus aureus and Bacillus subtilis) and Gram-negative (Escherichia coli, Klebsiella pneumoniae and Proteus mirabilis) bacteria were done using agar well-diffusion method. Complex 1 showed antibacterial activity against Gram-positive bacteria. Complexes 2 and 3 did not exhibit antibacterial activity. Complex 4 showed antibacterial activity and was chosen for further studies to determine the inhibition zone diameter for different concentrations and to set the minimum inhibitory concentration. The antibacterial activity against most of the bacteria was minimized as a result of the complexation of zinc ibuprofen with 2,2′-bipy in 4.     

Synthesis,characterization and antimicrobial activity of some new biquinoline derivatives containing a thiazole moiety

A series of new biquinoline derivatives containing a thiazole moiety were synthesized by a one-pot,base-catalyzed cyclocondensation reaction of 2-chloro-3-formyl quinoline,malononitrile and enaminone.All the synthesized compounds were characterized by elemental analysis,FT-IR,¹H NMR and ¹³C NMR data.All the synthesized compounds were screened against three bacterial pathogens,namely Bacillus cereus,B.substilis and Escherichia coli and for antifungal activity against three fungal pathogens,Aspergillus niger,Fusarium oxisporum and Rhizopus using the disc diffusion method.     

Synthesis,characterization and antimicrobial activities of new bis-hydrazonothioxothiazolidinone derivatives

New bis-hydrazonothioxothiazolidinone derivatives based on 2-thioxothiazolidin-4-one were synthesized in good yields using a simplified experimental condition. The structure of synthesized compounds was established with the help of common physico-chemical analysis and various spectroscopic techniques like FT-IR, mass and ¹H NMR. The results of characterizations are in good agreement with the proposed structure of all the synthesized compounds. Further, the antimicrobial (antibacterial and antifungal) activities of all the synthesized derivatives were carried out against various species like Bacillus subtilis, Escherichia coli, Aspergillous niger and Aspergillous flavus by using agar-cup method. The results of antimicrobial screening showed that all the compounds have mild to moderate activity. However, some of the compounds (3a, 3b, 3d, 3e, 3f, 3g, 3i and 3j) have shown better activity than the other.     

Synthesis,characterization and antimicrobial activity of triorganotin(IV) derivatives of some bioactive Schiff base ligands

Triorganotin(IV) complexes of the type Me₃Sn[OC(R¹):CH(CH₃)C:NR²OH] and Ph₃Sn[OC(R′):CH(CH₃)C:NR″OH] (R′ = ─CH₃, ─C₆H₅; R″ = ─(CH₂)₂─, ─(CH₂)₃─) have been synthesized by the reactions of trimethyl/phenyltin(IV) chloride with the sodium salt of corresponding Schiff base ligands in unimolar ratio in refluxing tetrahydrofuran. All these compounds have been characterized using elemental analyses and their probable structures have been proposed on the basis of infrared, ¹H NMR, ¹³C NMR, ¹¹⁹Sn NMR and mass spectroscopic studies. In the trimethyltin(IV) derivatives the central tin atom is tetracoordinated, whereas in the analogous triphenyltin(IV)derivatives the central tin atom is pentacoordinated. All these ligands, metal precursors and corresponding triorganotin(IV) complexes have been screened for antimicrobial activities. A comparison of activities of the ligands and their corresponding triorganotin(IV) derivatives has been made. Attempts have also been made to relate the activity to the structure of these compounds.     

Synthesis, characterization and antimicrobial activity of new 1,2,3-selenadiazoles

The commercially available aromatic polyketones 1a-d were utilized for the synthesis of the multi-arm1,2,3-selenadiazole derivatives 3a-d. The preparation starts with the reaction between compounds 1a-d and p-toluenesulfonyl hydrazide to give the corresponding tosylhydrazones 2a-d. Subsequent reaction with selenium dioxide leads to regiospecific ring closure of the tosylhydrazones to give the target multi-arm 1,2,3-selenadiazole derivatives in high yield. A 1,2,3-selenadiazole derivative 3e containing an epoxide ring was also prepared. The structures of all the synthesized compounds were confirmed on the basis of spectral and analytical data. The compounds were screened in vitro for their antimicrobial activity against various pathogenic bacterial and Candida strains obtained from King Abdullah Hospital in Irbid -Jordan. Compounds 3a, 3c and 3e were found to be highly active against all the selected pathogens. Compound 3e showed an inhibition zone of 13 mm against the highly resistant P. aruginosa.     

Polymer complexes. LXX. Synthesis,spectroscopic studies,thermal properties and antimicrobial activity of metal(II) polymer complexes

The monomer 3‐allyl‐5‐(phenylazo)‐2‐thioxothiazolidine‐4‐one (HL) was prepared by the reaction of allyl rhodanine with aniline through diazo‐coupling reaction. Reaction of HL with Ni(II) or Co(II) salts gave polymer complexes ( 1 – 8 ) with general stoichiometries [M(HL)(Cl)₂(OH₂)₂]_n, [M(HL)(O₂SO₂)(OH₂)₂]_n, [M(L)(O₂NO)(H₂O)₂]_n and [M(L)(O₂CCH₃)(H₂O)₂]_n (where M = Ni(II) or Co(II)). The structures of the polymer complexes were identified using elemental analysis, infrared and electronic spectra, molar conductance, magnetic susceptibility, X‐ray diffraction and thermogravimetric analysis. The interaction between the polymer complexes and calf thymus DNA showed a hypochromism effect. HL and its polymer complexes were tested against bacterial and fungal species. Co(II) polymer complex 2 is the most effective against Klebsiella pneumoniae and is more active than penicillin. The results showed that Ni(II) polymer complex 5 is a good antibacterial agent against Staphylococcus aureus and Pseudomonas aeruginosa. Molecular docking was used to predict the binding between the monomer with the receptors of prostate cancer (PDB code: 2Q7L Hormone) and breast cancer (PDB code: 1JNX Gene regulation). Coats–Redfern and Horowitz–Metzger methods were applied for calculating the thermodynamic parameters of HL and its polymer complexes. The thermal activation energy of decomposition for HL is higher than that for the polymer complexes.