Synthesis of some 3-phenyl chromenone-crown ethers and equilibrium studies on complexation with ion-pair extraction of sodium and potassium dyes

6,7-Dihydroxy-3-phenyl-2H-chromenones and 7,8-dihydroxy-3-(methoxyphenyl)-2H-chromenones, o-dihydroxy-3-phenylcoumarins, were prepared from phenylacetic acid/2,4,5-trihydroxybenzaldehyde, methoxyphenylacetic acid/2,3,4-trihydroxybenzaldehyde in NaOAc/Ac₂O, respectively. 3-Aryl-6,7-dihydroxy-2H-chromenone and 3-aryl-7,8-dihydroxy-2H-chromenone reacted with the polyethylene glycol ditosylate in CH₃CN/Me₂CO₃ to afford 12-crown-4,15-crown-5, and 18-crown-6-chromenones. The purified products were identified with IR, ¹NMR, low and high resolution mass spectroscopy and elemental analysis. Liquid–liquid extractive-spectrophotometric studies of sodium and potassium ion complexes of 3a–c, 4a–h coumarin-crown ethers and anionic dyes [4-(2-pyridylazo)-resorcinol monosodium salt monohydrate (SPAR), and sodium picrate (SP), and potassium picrate (PP)], as the counter ion are described. The overall extraction equilibrium constants for the 1:1 complexes of the above coumarin-crown ethers with sodium and potassium ions, between the organic solvent and water, have been determined at 25 °C. They were conducted in various solvent–water systems maintaining an identical initial cation concentration in water, [M₀⁺]_w, and a macrocyclic ligand concentration in the organic phase, [L₀]_org, so that in all extractions [M₀⁺]_w:[L₀]_org ratios were 1:1. An ion association complex formed between the alkali-crown ether complex ion and a dye anion was extracted into the CH₂Cl₂ organic solvent, and then the dye concentration of the separated aqueous phase was measured with an ultraviolet–visible spectrophotometer. According to the study, SPAR is the best associated dye with all the coumarin-crown ethers and the extracted dye occurs as the ion-pair complex. The extraction selectivity was interpreted quantitatively by the constituent equilibrium constants, i.e. K_ext, the ion-pair extraction constant of ML⁺ and A⁻ in CH₂Cl₂.     

一种新型喹啉类衍生物的合成与结构表征

以3,4,5-三甲氧基苯甲醛、苯并环己酮和丙二腈为原料,在醋酸铵的存在下,通过Knoevenagel反应和Mannich反应的串联反应合成了一种新型喹啉类衍生物,采用IR,MS1HNMR,13CNMR对该衍生物进行了表征,并通过X-单晶衍射获得其晶体结构.     

Synthesis of poly‐N‐(thiazol‐2‐yl)methacrylamide: Characterization,complexation, and bioactivity

Cu(II) complexes with N‐(thiazol‐2‐yl)methacrylamide (NTM) and its polymer PNTM have been synthesized. The ligands (NTM and PNTM) and their Cu(II) complexes have been characterized by FTIR and ¹H‐NMR. EDX was performed to know the elemental composition and X‐ray powder diffractometry (XRD) analysis was applied to detect the crystallinity of the complexes. The morphology of these complexes was investigated with scanning electron microscopy (SEM) and proves that the monomer complexes have a strongly crystalline structure compared with the polymer complexes, which show that it is only weakly crystalline. These results from SEM are in agreement with results obtained from XRD. Thermal properties of the ligands and their complexes have been studied by thermogravimetric analysis and differential scanning calorimetry. The activity of the ligands and their complexes has been screened against S. aureus, E. coli, Pseudomonas, and Candida albicans. The synthesized compounds have shown good affinity as antibacterial and antifungal agents, which increased on complexation with Cu(II) ion. The results of these studies show the Cu(II) complexes to be more thermal stable as compared with NTM and PNTM. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

7-苄氨基-9,10-二氢-1,2,4-三氮唑并[4,3-a]喹啉衍生物的合成

以6-氨基-3，4-二氢-2(1H)-喹啉酮为起始原料，经缩合、还原、硫代、环合等反应合成了5个未见报道的7-苄氨基-9，10-二氢-1，2，4-三氮唑并[4，3-a]喹啉衍生物。产物及中间产物的结构经红外光谱和核磁共振谱确证。     

含偶氮苯(喹啉)结构化合物的合成、表征及发光性能

以间苯二甲酸为原料,合成了新型偶氮苯-喹啉化合物—5-(8-羟基喹啉-5-偶氮)-1,3-苯二甲酸二乙酯,通过IR、UV-vis、1H NMR对其结构和性能进行了表征,利用荧光发射光谱研究了目标化合物的发光性能。结果表明,目标化合物(2.0×10-5 mol/L的THF溶液)以311 nm光激发,在450 nm处发射蓝紫色荧光。     

1,1'-二芳基烷基醚化合物的合成及生物活性

利用氯苄和苄醇为原料,NaOH为缚酸剂合成了8个未见文献报道的1,1, 二芳基烷基醚类化合物,目标化合物经元素分析、IR、MS和1HNMR结构确证;初步生物活性测定结果表明:该类化合物具有虫、菌、草等广谱生物活性,如Ig在普筛浓度下(5.0×10-4)对蚜虫具有A级活性(>95%的死亡率),Ic在普筛浓度(2250ga.i./hm2)下,苗后茎叶处理对马齿苋和反枝苋均具有100%的防治效果。     

πSynthesis and evaluation of a series of α-hydroxy ethers derived from isopropyl oleate

Several fatty derivatives with bulky moieties were prepared by treatment of epoxidized isopropyl oleate with a number of alcohols in the presence of sulfuric acid catalyst to provide a series of α-hydroxy ethers in good yield. The materials were analyzed for cold flow performance through cloud point and pour point determinations. The most promising α-hydroxy ether produced in this study, with respect to both low temperature behavior and economic criteria, was isopropyl 9(10)-(2-ethylhexoxy) 10(9)-hydroxystearate, which has a cloud point of −23°C and pour point of −24°C.     

Ebselen氨基酸衍生物的合成与生物活性研究

在药物分子2-苯基苯并[d][1,2]-硒唑-3（2H）-酮（Ebselen）的分子结构中，将其2-位苯环更换为不同的氨基酸，设计并合成了2种Ebselen类似物，体外筛选试验表明该衍生物对肿瘤细胞生长有明显的抑制作用。     

Hybridized 4-Trifluoromethyl-(1,2,3-triazol-1-yl)quinoline System: Synthesis,Photophysics, Selective DNA/HSA Bio-interactions and Molecular Docking

The synthesis, structural analysis, and evaluation of the photophysical properties of twelve novel 2-aryl(heteroaryl)-6-(4-alkyl(aryl)-1H-1,2,3-triazol-1-yl)-4-(trifluoromethyl)quinolines ( 6-8 ), where aryl(heteroaryl)=Ph, 4-Me-C₆H₄, 4-F-C₆H₄ and 2- furyl; 4-alkyl(aryl)=−CH₂OH, −(CH₂)₅CH₃ and Ph, are reported. Hybrid scaffolds 6 – 8 were synthesized at 77–95 % yields by regioselective copper-catalysed azide-alkyne cycloaddition (CuAAC) reaction of unpublished 6-azido-4-(trifluoromethyl)quinolines ( 2 ) with selected terminal alkynes ( 3 – 5 ). Azido intermediates 2 were obtained from the reaction of 6-amino-4-(trifluoromethyl)quinolines ( 1 ) and sodium azide at good yields (78–87 %). Compounds 6 – 8 were structurally fully characterized by ¹H−, ¹³C− and ¹⁹F− and ¹H−¹³C 2D-NMR (HSQC, HMBC) spectroscopy, X-ray diffraction (SC-XRD) and HRMS analysis. Moreover, the photophysical properties, DNA- and HSA-binding experiments (bio-interactions), and molecular docking studies for compounds 6 – 8 were performed. These are discussed and compared with similar compounds from recent research.     

两种新型含硅植物生长调节剂的合成及其生物活性

合成了2种新型含硅植物生长调节剂。它们的结构经元素分析、IR和^1HNMR表征。生物活性试验表明,药液质量浓度为25mg/L时,2种目标化合物对水稻根生长比对照化合物1-萘乙酸乙基二甲硅基酯分别提高了10%和13%。     

Synthesis,characterisation and cytotoxicity studies of Manganese(I) and Rhenium(I) based metallacrown ethers

Manganese(I) and Rhenium(I) based metallacrown ethers [M(CO)₃Br(μ-pcatgd)] (1, M = Mn; 2, M = Re) were synthesised by the reaction of M(CO)₅Br (M = Mn, Re) and pyridine appended bidentate ligand crafted with flexible polyether spacer. The self-assembled mononuclear compounds 1 and 2 were characterised by IR, NMR, UV–Visible absorption and emission spectroscopic techniques. Molecular structure of 2 was determined by single-crystal X-ray diffraction methods and the molecular masses of 1 and 2 were confirmed by ESI–mass spectrometry. Anticancer activities of compounds 1 and 2 were investigated by in vitro cytotoxicity studies against different cancer cell lines as well as on normal cells. Compounds 1 and 2 showed a broad-spectrum inhibition on few cancer cells that were comparable to cisplatin. Compound 1 exhibited selective inhibition of cancer cells upon irradiation at λ_max 365 nm in dose-dependent manner. Morphological studies showed the induction of apoptosis in compound 1-treated cancer cells upon irradiation. The UV–Visible absorption spectroscopy-based myoglobin assay further supported the nature of compound 1 as photoactivatable CO releasing molecule (PhotoCORM).     

7-苄氨基-9,10-二氢-1,2,4-三氮唑并[4,3-a]喹啉衍生物的合成及环合反应的探讨

以6-氨基-3,4-二氢-2(1H)-喹啉酮为起始原料,经缩合、还原、硫代、环合等反应合成了5个7-苄氨基-9,10-二氢-1,2,4-三氮唑并[4,3-a]喹啉衍生物。产物的结构经核磁共振谱和质谱确证。     

Synthesis of some novel 2-oxo-pyrano(2,3-b)- and 2-oxo-pyrido(2,3-b)quinoline derivatives as potential antimalarial,diuretic, clastogenic and antimicrobial agents

The 2-chloro-3-formyl quinoline derivatives ( 1a–e ) on treatment with acetic anhydride and sodium acetate, afforded the corresponding novel 2-oxo-pyrano(2,3-b) quinoline derivatives ( 2a–e ), and these were subjected to ammonia treatment to yield the corresponding naphthyridine derivatives ( 3a–e ). The prepared compounds ( 2a–e ) were tested for their antimalarial, diuretic, clastogenic and antimicrobial properties. Not all the compounds showed a diuretic effect and the significant increase in the frequency of micronuclei shows that they are non-clastogens, whereas the 7-chloro derivative ( 2e ) was a very effective antimalarial agent against the mosquito species. All the compounds were found to have optimum antimicrobial activity against Staphylococcus aureus, Escherichia coli and Salmonella typhi. Compounds 2d and 2e were found to be most active against the bacteria tested. © 1998 SCI     

Amide derivatives of poly(3,4-dimethylenepyrrolidine): Synthesis,characterization, and complexation studies

Improved synthesis of polydiallylamine provides ready access to an entire family of amide-functionalized polymers. Complete conversion to the acetamide derivative was attained under mild conditions. Formation of the formamide polymer required harsher conditions and did not give complete functionalization. The formamide polymer displayed typical polyelectrolyte behavior caused by residual amine units. Complexation with iodine and transition metal cations was strong as shown by UV, IR, and ¹³C-NMR evidence indicating potential of these polymers for trace metal recovery, waste water treatment, and antiseptic formulations.     

Synthesis and biological evaluation of pyrazolylnaphthoquinones as new potential antiprotozoal and cytotoxic agents

The importance of American trypanosomiasis (Chagas' disease) in human pathology is widely known. The prognosis of this disease is poor and the choice of effective medicines limited, thus study of new drugs is absolutely necessary. In this work, the activities of three new pyrazolylnaphthoquinones, heterocyclic naphthoquinones bearing 3-aminopyrazole rings, were evaluated on Trypanosoma cruzi, the etiological agent of Chagas' disease. These activities were compared with those of three 5-aminoisoxazole analogues. In addition, since these compounds belong to a family of antiprotozoal and cytotoxic/antitumor agents, the activities of all six against Plasmodium falciparum, Trypanosoma brucei rhodesiense, and murine L-6 cells were also investigated. In the biological tests, five of the compounds showed significant in vitro trypanocidal activities against T. cruzi, with activities similar to that of benznidazole. Two of the 5-aminoisoxazole analogues also showed good activities, in one case highly selective, against the K1 and NF54 strains of P. falciparum (IC(50)<0.12 microg mL(-1)). Three of the compounds were cytotoxic to murine L-6 cells (IC(50)=0.21-0.50 microg mL(-1)). The results suggested that the three pyrazolylnaphthoquinones and one of the 5-aminoisoxazole analogues could be starting points for lead optimization programs against T. cruzi and P. falciparum, respectively.     

Synthesis,extraction, and anti‐bacterial studies of some new bis‐1,2,4‐triazole derivatives part I

A series of new bis triazole Schiff base derivatives (4) were prepared in good yields by treatment of 4‐amino‐3,5‐diphenyl‐4H‐1,2,4‐triazole (3) with bisaldehydes (1). Schiff bases (4) were reduced with NaBH₄ to afford the corresponding bisaminotriazoles (5). All the new compounds were characterized by IR, ¹H NMR and ¹³C NMR spectral data. Their overall extraction (log K_ex) constants for 1 : 1 (M : L) complexes and CHCl₃/H₂O systems were determined at 25 ± 0.1°C to investigate the relationship between structure and selectivity toward various metal cations. The extraction equilibrium constants were estimated using CHCl₃/H₂O membrane transfer with inductively coupled plasma‐atomic emission spectroscopy spectroscopy. The stability sequence of the triazole derivatives in CHCl₃ for the metal cations was exhibited a characteristic preference order of extractability to metal ions [Fe(III) > Cu(II) > Pb(II) > Co(II) > Ni(II) > Mn(II) > Zn(II) > Mg(II) > Ca(II)]. The compounds were tested for anti‐microbial activity applying agar diffusion technique for 11 bacteria. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2012     

Synthesis and properties of hydrophilic polymers,part 11: Synthesis,biodegradability, and metal complexation of copolymers of ethylenediaminetetraacetic acid dianhydride and lactose

The synthesis and characterization of poly(ethylenediaminetetraacetic acid‐co‐lactose) of high molar mass (132 kg mol^?1) is described. The polycondensate with pendant carboxylic groups was shown to be hydrolytically and microbiologically degradable by using conventional microbiological methods. The metal complexing properties of the polyester were studied for Cr(III), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Sr(II), Cd(II), Pb(II), and Al(III) ions in aqueous solution using the liquid‐phase polymer‐based retention (LPR) method. In addition, the complexing capacity of the Cu(II)‐saturated copolymer was determined by TGA to be 182 mg g^?1 polymer. According to the retention profiles determined as a function of filtration factor by using LPR in conjunction with inductively coupled plasma spectrometry, Cr(III) and Fe(III) showed a strong interaction with this polymer under these conditions, indicated by retention values of 100% at pH 5. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 103: 2932–2939, 2007     

Application of polymeric nanofibers in medical designs,part IV: Drug and biological materials delivery

Nanotechnology has potential applications in different sciences, especially in the biological sciences and medicine. The development of nanofibers has greatly enhanced the scope for fabricating designs that can potentially use in medical sciences. Nanofibers mimic the porous topography of natural extracellular matrix, and are advantageous for tissue regeneration and also sustained release of encapsulated drug or growth factor. In part IV the author summarizes the currently available applications of nanofibers in drug and biological materials delivery.     

Synthesis,spectral behaviour and biological activity of pyrazolo-pyrimidine cyanine dyes

New asymmetrical 2(4)-monomethine cyanine dyes (III_a-_c IV_a-_i), monomethine bases (V_a,b), dicationic cyanines (VIII_a__c, IX_a-_c) and styryl cyanines (XI_a-_b) incorporating N-phenyl-1-H-pyrazolo (3, 4-d) saturated or unsaturated pyrimidine were prepared. The new cyanines were identified by spectral determination. Bactericidal and fungicidal activity of selected cyanines (III_a-c, IV_a-i, V_a,bVIII_a-_c, IX_a-c and XI_a,b) were tested against bacterial and fungal strains.     

New heteroaromatic polyazomethines containing naphthyridine moieties: Synthesis,characterization, and biological screening

A new series of heteroaromatic polyazomethines containing 1,8‐naphthyridine moieties in the polymer backbone were synthesized with a solution polycondensation technique. A new heteroaromatic monomer containing 1,8‐naphthyridine moieties (4‐ethoxy‐2,7‐dicarboxaldehyde‐1,8‐naphthyridine) was synthesized with an analogous synthetic sequence and confirmed by elemental and spectral data. The resulting polymers were characterized by elemental, spectral analyses, solubility and viscometry measurements. All the synthesized polyazomethines had better solubility in polar aportic solvents. The thermal properties of those polymers were evaluated by thermogravimetric analysis, differential thermogravimetry, and differential thermal analysis measurements and correlated to their structural units. All the polymers had nearly similar maximum polymer decomposition temperatures, which were in the range 557–577°C. A very large difference between the glass transitions (92–222°C) was observed. In addition, with gel permeation chromatography, the molecular weight determination of selected examples of those polymers was evaluated. The values of the average molecular weight for polyazomethines 7 _b and 7 _c were 34,914 and 24,859, respectively. On the other hand, the biological screening of all of the synthesized polyazomethines was performed in variety of bacteria and fungi. Most of the polyazomethines showed a significant influence against Gram‐negative bacteria. The minimum inhibitory concentration of the most active polymers was 0.05 mg/mL. © 2012 Wiley Periodicals, Inc. J Appl Polym Sci, 2012