Fluorene Derivatives with Multi-addressable Properties: Synthesis,Characterization, and Reactivity

A series of novel fluorene derivatives were synthesized from the target compound N-octadecyl-9-oxo-9H-fluorene-4-carboxamide (3), which led to new functionalized five- and six-membered heterocyclic derivatives via reaction with various reagents. The synthesized compounds were allowed to react with propylene oxide to afford unique surface-active properties. The chemical structures of the newly synthesized compounds were elucidated and confirmed by spectroscopic and analytical tools. The synthesized compounds have good surface activity and the biological degradation of these fluorene-based surfactants was greater than 96% after 7 days.     

Synthesis and optical properties of novel, thermally stable phenanthrolines bearing an arylthienyl-imidazo conjugation pathway

Six new hyperpolarizable chromophores based on functionalized arylthiophene donors and an imidazo-phenanthroline acceptor moiety have been designed and synthesized for the first time in good to excellent yields by condensation of 5,6-phenantroline-dione with formyl-arylthiophene derivatives in the presence of ammonium acetate in glacial acetic acid. The thermal stability, solvatochromic and nonlinear optical properties of these compounds were evaluated.     

Vinyl carbazole (VC) functionalized mesoporous silica polymer nanocomposites (SBA/VC) for the antibacterial activity studies

Vinyl carbazole (VC) functionalized ordered mesoporous silica polymer nanocomposites (SBA/VC) were synthesized by in situ radical polymerization of monomers inside the mesoporous framework and characterized for the antibacterial activity studies against gram positive and gram negative bacteria. Powder X-ray diffraction and N₂ adsorption isotherms of SBA/VC nanocomposites showed the presence of mesoporous nature. The antimicrobial activity results showed increasing trend with the increase in the concentration of vinyl carbazole (VC) and the maximum antibacterial activity was achieved with SBA/VC₆₄ nanocomposites.     

Fatty Acids in Heterocyclic Synthesis. Part XIV: Synthesis of Surface Active Agents from Some Novel Class of Oxadiazole,Thiadiazole and Triazole Derivatives Having Microbiological Activities

Reaction of stearic acid with semicarbazide in refluxing POCl₃ afforded 2-amino-5-heptadecyl 1,3,4-oxadiazole. Acylation of the amino group with acetic anhydride, ethyl chloroacetate and chloroacetic acid gave amide and β-amino acid derivatives. These compounds were cyclized to imidazo[2,1-b]oxadiazole derivatives by two different techniques. Treating the starting oxadiazole compound with P₂S₅, hydroxyl amine and hydrazine hydrate in benzene afforded thiadiazole and triazole derivatives. Unexpectedly, triazolo[3,4-b][1,3,4]oxadiazole derivative was obtained when 1,3,4-oxadiazole derivative was refluxed with hydrazine hydrate in ethanol. The biological activities of the synthesized compounds were screened in vitro against some gram positive and gram negative bacteria and fungi. Addition of quantitative amount of propylene oxide units (3, 5, 7 mol) to the synthesized compounds afforded new nonionic surfactants. The physico-chemical and surface properties of the novel synthesized surfactants such as surface and interfacial tension, cloud point, wetting time, emulsion stability, foam height, CMC, resistance to hydrolysis and their biodegradability were investigated. In addition, surface parameters including effectiveness (π _CMC), efficiency (PC₂₀), maximum surface excess (Γ_max) and (A _min) were examined.     

Novel Imidazolium-Based Gemini Surfactants: Synthesis, Surface Properties, Corrosion Inhibition and Biocidal Activity Against Sulfate-Reducing Bacteria

Three novel imidazolium-based gemini surfactants had been synthesized and characterized using different spectroscopic techniques. The surface properties of the synthesized surfactants were determined using surface tension measurements at 20 °C. The surface parameters including critical micelle concentration (CMC), π _CMC, Pc₂₀, Γ_max and A _min were determined. The synthesized compounds were evaluated as corrosion inhibitors for carbon steel in 0.5 M HCl solution using the weight loss and polarization techniques. The biological activity of these surfactants was evaluated against sulfate reducing bacteria using most probable number method. The results indicate that the synthesized compounds have good surface properties and are proper corrosion inhibitors for low carbon steel, with a high inhibition efficiency observed around their CMC. These compounds exhibit a significant biocidal activity against sulfate reducing bacteria.     

Synthesis,Biological Study and Complexation Behavior of Some Anionic Schiff Base Amphiphiles

A novel series of anionic Schiff base amphiphiles were synthesized. The chemical structures of these compounds were elucidated using different spectroscopic tools. The surface and thermodynamic properties of the prepared Schiff bases were studied using classical measurements including surface and interfacial tensions. The surface parameters of these compounds, e.g., surface tension, critical micelle concentration, effectiveness, efficiency, maximum surface excess, minimum surface area, and interfacial activity showed their good surface activity. Their thermodynamic parameters of adsorption and micellization including free energy change of micellization and adsorption showed their tendency toward adsorption at the interfaces and also micelle formation at lower concentrations. The complexation behavior of the synthesized Schiff bases were study through the interaction of the Schiff base (IIIa; SBSD) with nickel chloride hexahydrate. All synthesized compounds in addition to NiCl₂·6H₂O and Ni Schiff Base complex have been evaluated for their antibacterial activity against Gram-positive and Gram-negative bacteria. The results of the biocidal activities showed high potent action of (Ni-III_a; Ni-SBSD) complex more than Schiff base IIIa; SBSD.     

Design,Synthesis, in vitro and in silico Characterization of 2-Quinolone-L-alaninate-1,2,3-triazoles as Antimicrobial Agents

Due to the ever-increasing antimicrobial resistance there is an urgent need to continuously design and develop novel antimicrobial agents. Inspired by the broad antibacterial activities of various heterocyclic compounds such as 2-quinolone derivatives, we designed and synthesized new methyl-(2-oxo-1,2-dihydroquinolin-4-yl)-L-alaninate-1,2,3-triazole derivatives via 1,3-dipolar cycloaddition reaction of 1-propargyl-2-quinolone-L-alaninate with appropriate azide groups. The synthesized compounds were obtained in good yield ranging from 75 to 80 %. The chemical structures of these novel hybrid molecules were determined by spectroscopic methods and the antimicrobial activity of the compounds was investigated against both bacterial and fungal strains. The tested compounds showed significant antimicrobial activity and weak to moderate antifungal activity. Despite the evident similarity of the quinolone moiety of our compounds with fluoroquinolones, our compounds do not function by inhibiting DNA gyrase. Computational characterization of the compounds shows that they have attractive physicochemical and pharmacokinetic properties and could serve as templates for developing potential antimicrobial agents for clinical use.     

Aminimides: II. Antimicrobial effect of short chain fatty acid derivatives

A new family of surfactants, aminimides, has been screened forin vitro antimicrobial activity. These compounds are active against both bacteria and yeast, activity being a function of chain length. Maximum activity for acetimide and acrylimide amine derivatives was extablished with chain lengths of C₁₄–C₁₆. Homologous compounds with lower or higher chain lengths were less active. While showing low antimicrobial activity against gram negative bacteria, mixtures containing C₁₂ and C₁₆ gave good activity against gram negative strains without losing gram positive activity. Aminimides gave low acute LD₅₀’s (200–400 mg/kg) when tested in mice by intraperitoneal injection.     

Synthesis,Structure Characterization and Biological Activity of Co (II), Cu (II), and Zn (II) Complexes with (Z)‐3‐((3‐hydroxybenzylidene)amino)pyridin‐1‐ium 4‐(dodecan‐4‐yl)benzenesulfonate Surfactant

(Z)‐3‐((3‐hydroxybenzylidene)amino)pyridin‐1‐ium4‐dodecylbenzenesulfonate anionic surfactant and its cobalt, copper and zinc complexes were synthesized (I, I‐Co, I‐Cu and I‐Zn). The chemical structures of it were characterized by elemental analysis, FTIR, ¹H‐NMR, UV–Vis spectroscopy and atomic adsorption. The effects of the chemical structures of the synthesized anionic surfactant and the type of transition metals on the surface activity are presented in this paper. The thermodynamic parameters show that adsorption and micellization processes are spontaneous. The results of biological activity measurements showed that the synthesized compounds have a great efficiency against gram positive (Bacillus subtilis and Staphylococcus aureus), gram‐ negative bacteria (Pseudomonas aeruginosa and Escherichia coli) and fungi (Candida albicans and Aspergillus niger) as well as the sulfate reducing bacteria (Desulfomonas pigra). The complexation of the anionic surfactant with Co²⁺, Cu²⁺ and Zn²⁺ increase the antimicrobial activity values.     

Highly efficient recovery of bioactive ingredients from solid waste of onions onto functionalized SWCNTs supported on amberlite nanocomposite

Preparation of single-walled carbon nanotubes (SWCNTs) with carboxylic (–COOH) acid was executed by functionalization with amine functional groups (–NH2). The obtained functionalized SWCNTs were supported by macroporous resin (amberlite XAD-7HP). The synthesized nanocomposite has been characterized by scanning electron microscopy (SEM) and Fourier transform infrared spectroscopy (FTIR) methods. FTIR analysis indicates that functionalized SWCNTs supported onto the amberlite resin were synthesized successfully. The surface morphology of the nanomaterial was also successfully embedded into the amberlite of the functionalized SWCNTs. Huge solid residues of onions are produced as agricultural and food wastes each year. The related biowaste includes biologically active phenolic compounds which have positive effects with strong antioxidant properties on human health when properly isolated and concentrated. In the present research, functionalized SWCNTs have been utilized for the separation of bioactive phenolics from onion waste extracts. Equilibrium (Langmuir, Freundlich and Toth) and kinetic (pseudo-first order, pseudo-second order, intraparticular diffusion and Elovich) models have been applied for analysis and representation of data. Pseudo-second-order model is in good agreement with the experimental data. On the other hand, the equilibrium findings were represented best with Freundlich isotherm model. Additionally, thermodynamic indicators have also demonstrated that the current system is a spontaneous and exothermic chemisorption process.     

Potentialities of oilseed flours and proteins for replacing black gram components in the texture of leavened foods

Defatted peanut and sesame flours in aqueous dispersions exhibit good surface activity ascribable to their protein content and com-parable to that of black gram. Soy flour possesses twice as much surface activity as the other flours. Contrasted with black gram, foam matrices obtained with these dispersions are unstable to heat and have low viscosities. Addition of viscous polysaccharide stabil-ized the foam against thermal disruption. Oilseed flours appear to qualify as good alternatives for the surface active component and viscous hydrocolloids such as guar gum or gelatinized starch may be alternatives for the arabinogalactan of black gram. This combination effectively replaces the pulse in imparting the characteristic soft, spongy texture to leavened foods.     

Sulfonic Acid‐Functionalized Ionic Liquids as Metal‐Free,Efficient and Reusable Catalysts for Direct Amination of Alcohols

A series of sulfonic acid‐functionalized (SO₃H‐functionalized) ionic liquids was synthesized and used as metal‐free, highly selective and efficient catalysts for the direct amination of alcohols. Notably, the activities of the series of SO₃H‐functionalized ionic liquids were compared and a 92% isolated yield was obtained using 3‐tetradecyl‐1‐(butyl‐4‐ sulfonyl)imidazolium trifluoromethanesulfonate ([BsTdIM][OTf]) as the catalyst. Importantly, the catalytic system has wide substrate scope including benzylic, allyl, propargylic, aliphatic alcohols with sulfonamide, amide, carbamate, aromatic amine and N‐heterocyclic compounds. Interestingly, the system was also suitable for a multi‐gram scale direct amination of alcohols. Additionally, the reusable nature of [BsTdIM][OTf] makes this protocol more attractive and avoids the disposal and neutralization of acidic catalysts. Moreover, preliminary experiments indicated that this reaction should proceed via an S_N1 pathway.     

Antimicrobial activity and physical characteristics of some N,N-Disubstituted decanamides

A number of N,N-disubstituted decanamides have been prepared, characterized and screened for their antimicrobial activity against a number of pathogenic organisms including bacteria both gram positive and negative, yeasts and molds. Several of these compounds exhibited a broad spectrum and high level of activity against all or most of the test organisms. The antimicrobial activity of these compounds has been shown to correlate with their dispersibility and surface tension in an aqueous systems. So. Utiliz. Res. Dev. Div., ARS, USDA.     

Synthesis,Characterization and Surface Activity of New Eco-friendly Schiff Bases Vanillin Derived Cationic Surfactants

Three eco-friendly cationic surface active agents were synthesized from the chemical modification of vanillin. The chemical structures of these surfactants were confirmed using elemental analysis, IR and NMR spectra. The surface activity measurements showed their high tendency towards adsorption and micellization and their good surface tension reduction, low interfacial tension. The emulsion stability measurements showed acceptable efficiency as emulsifying agents for short term emulsions. The biodegradability tests revealed that these compounds are eco-friendly and had completely degraded in 30 days.     

新型喹唑啉化合物的合成与生物活性

设计并合成4类新型喹唑啉化合物,进行医药和农药的联合筛选,生物活性测试表明部分新化合物具有较好的生物活性。     

Characterization,surface properties and biological activity of new prepared cationic surfactants

Three cationic surfactants were prepared. A condensation reaction between dimethylaminopropylamine (DMAPA) and benzaldehyde was performed. The produced Schiff base was quaternization with three fatty alkyl bromide with different carbon chain length separately to form the desired cationic surfactants. The chemical structure of synthesized cationic surfactants was confirmed by FTIR, ¹H NMR and mass spectroscopy. It was found that the chemical structure of prepared compounds has an effect on surface properties, where increasing the hydrophobic chain length decrease the values of CMC, Г_max while A_min value was increased. The thermodynamic parameters showed that adsorption and micellization processes are spontaneous. It is clear that the prepared cationic surfactants at first tend to adsorb at surface, then it aggregate to form micelle. The prepared surfactants showed good biological activity against gram positive and negative bacteria and fungi in the following order of II (C12) > I (C10) > III (C16). The serial dilution method was used to evaluate the inhibiting effect of these compounds on the sulfate reducing bacteria growth.     

Pyrazole Derived Cationic Surfactants and their Tin and Copper Complexes: Synthesis,Surface Activity,Antibacterial and Antifungal Efficacy

Five membered heterocyclic cationic 3-pyrazolium surfactants namely: 2-[2-(alkyloxy)-2-oxoethyl]-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-3-pyrazolium bromide (decyl-; dodecyl-) and their copper and tin complexes were synthesized, their structures were confirmed using different spectroscopic tools. The IR spectra of the metal complexes showed that these compounds exhibit a tetrahedron structure with the transition metal ion (M²⁺) at the center and the cationic ligands arranged in the apexes, while the halide ions in the center. The synthesized compounds were evaluated as biocides against different types of bacteria and fungi. The biological activity data showed that the cationic surfactants exhibit moderate to high efficacy against the tested microorganisms (either bacteria or fungi). While, complexation of these cationic surfactants with Cu (II) and Sn (II) ions the antimicrobial activity was strongly increased. The surface activity of these compounds were discussed and correlated to their chemical structure and the type of substituents on the heterocyclic moiety. Meanwhile, the antimicrobial assay was correlated to the surface activities of the synthesized compounds.     

Self‐segregating hyperbranched polymer/silver nanoparticle hybrids in thermoplastic polyurethane films

Self‐segregating hyperbranched polymer (HBP) additives have been utilized to concentrate silver nanoparticles (AgNPs) at the air interface of polyurethane films. The limited spontaneous surface migration of the AgNPs was enhanced through the addition of appropriately functionalized HBPs. Both amine and thiol terminated additives were employed to allow interaction of the HBP with the nanoparticles. Both types of additives increased surface concentration of silver modestly, though the thiol‐terminated HBPs demonstrated nearly a seven‐fold enhancement of surface migration. It was also found that wholly‐aliphatic HBPs demonstrated only slightly reduced ability to bias AgNP concentration as compared to HBPs functionalized with perfluorinated chains. In addition, films containing 1% total silver concentration were tested for antimicrobial activity using the ASTM‐E 2180 protocol. Significant reduction of the microorganisms was observed for all samples, 6‐log reduction was achieved for the gram‐negative bacteria P. aeruginosa, the gram‐positive bacteria S. aureus, and the fungi C. albicans. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

Sugar-Based Ester Quaternary Ammonium Compounds and Their Surfactant Properties

Two sugar‐based ester quaternary ammonium compounds were synthesized and their surface behavior and antimicrobial activity were investigated. The compatibility with anionic surfactant sodium dodecyl sulfate (SDS) was further studied. Results indicated that the synthesized cationic surfactants showed high surface activity and good synergistic effects with SDS.     

Design,Synthesis, and Evaluation of ω‐(Isothiocyanato)alkylphosphinates and Phosphine Oxides as Antiproliferative Agents

A series of 21 novel, structurally diverse ω‐(isothiocyanato)alkylphosphinates and phosphine oxides (ITCs) were designed and synthesized in moderate to good yields. The synthesized compounds were evaluated for in vitro antiproliferative activity using LoVo and LoVo/DX cancer cell lines. The biological activity of the synthesized compounds was higher than that of natural isothiocyanates such as benzyl isothiocyanate or sulforaphane. The antiproliferative activity of selected ITCs was also tested on selected cancer cell lines: A549, MESSA and MESSA/DX‐5, HL60 and HL60MX2, BALB/3T3, and 4T1. These compounds were assessed for their mechanism of action as inducers of cell‐cycle arrest and apoptosis. Ethyl (6‐isothiocyanatohexyl)(phenyl)phosphinate ( 71 ) was tested in vivo on the 4T1 cell line and demonstrated moderate antitumor activity, similar to that benzyl isothiocyanate and cyclophosphamide.