Synthesis and optical properties of bis- and tris-alkynyl-2-trifluoromethylquinolines.

Three bis- or tris-brominated 2-trifluoromethylquinolines have been successfully applied in palladium-catalysed Sonogashira reactions, leading to several examples of alkynylated quinolines in good to excellent yields. Optical properties of selected products have been studied by steady state absorption and fluorescence spectroscopy which give insights of the influence of the substitution pattern and of the type of substituents on the optical properties.

Swelling Behavior of Novel Hydrogels Produced from Glucose-Based Ionic Monomers with Varying Cross-Linkers.

This work presents the synthesis of glucose-based vinyl imidazolium monomers and the hydrogels produced thereof. These novel semisynthetic, cationic hydrogels were prepared by radical polymerization with different types of commercial cross-linkers such as N,N'-methylenebis(acrylamide) or poly(ethylene glycol) diacrylate. Both the type and the amount of cross-linker were investigated as influencing factors with respect to the swelling degree. It was found that the cross-linker type majorly influences the swelling degree and long-term stability of the hydrogels. Last, the influence of different anions (e.g., halogens, acetate, and triflate) in the monomer molecule on the swelling properties of the hydrogels was investigated.

Excellence in Acrylation - Scope and Limitation of Glucosyl Imidazolium-coated Novozym 435 Catalyzed (Meth)acryl Ester Synthesis.

The incorporation of carbohydrate based ionic liquids as a support for Novozym 435 was previously studied by the authors for the acrylation of n-butanol as the target substrate, which was used as the foundation for the design of experiments. The combination of carbohydrate based ionic liquids and Novozym 435 remains a key aspect of this work. Building upon this, the reaction parameters were optimized for the Novozym catalyst. Substrate screening was performed to explore the scope and limitations of room temperature acrylation reactions. Herein, different alcohols and reaction conditions were screened extensively for the different acrylate products with yields of up to 99.9 % determined via gas chromatography (GC). Standard straight chain alcohols, 2-functionalized ethanol derivatives with electron donating and withdrawing groups, and more sterically challenging substrates were investigated over a broad concentration region. To further underline the applicability of the modified biocatalyst, two alcohols were converted with methacrylic acid. The presented method offers a greener pathway for acrylate synthesis, which eliminates the need for high reaction temperatures, strongly acidic catalysts and/or polymerization inhibitors as used in non-biocatalytic acrylate synthesis.

1-(Methyl-α-d-gluco-pyran-osid-6-yl)-3-vinyl-imidazolium iodide di-methyl-formamide monosolvate.

The title solvated molecular salt, [MeGluVIm]I (MeGluVIm = 1-(methyl-α-d-gluco-pyran-osid-6-yl)-3-vinyl-imidazolium), or C12H19N2O5 +·I-·C3H7NO, was synthesized from methyl-α-d-6-iodo-gluco-pyran-oside and vinyl-imidazole in DMF. It crystallizes through precipitation from ethyl acetate solution directly after the reaction procedure. The crystal structure consists of an iodide anion and a [MeGluVIm] cation. Furthermore, the crystal structure contains one mol-ecule of DMF, which accepts two O-H⋯H hydrogen bonds from the OH groups of the gluco-pyran-oside.

Novel Glucosylimidazolium Ionic-Liquid-Supported Novozym 435 Catalysts - A Proof of Concept for an Acrylation Reaction.

Invited for the cover of this issue is the group of Stefan Jopp at the University of Rostock. The image depicts the conversion of acrylic acid and n-butanol into butyl acrylate through an engine of Novozym 435, in which the powering piston CalB (Candida antarctica lipase B) is supported by the newly developed GMIM-I (glucosyl-methyl-imidazolium iodide). The authors acknowledge Dr. Johanna Meyer (University of Hannover) for the creation of the cover image. Read the full text of the article at 10.1002/open.202200135.

Novel Glucosylimidazolium Ionic-Liquid-Supported Novozym 435 Catalysts - A Proof of Concept for an Acrylation Reaction.

A series of novel ionic liquids based on glucose was synthesized in high yields in simple two or three-step reaction procedures. These carbohydrate-based ionic liquids were studied and compared to commercially available imidazolium-based ionic liquids as supports for Novozym 435 in the acrylation of n-butanol. A direct correlation between the availability of hydroxy groups and the overall activity as well as an enhanced recyclability of the biocatalyst has been found for the glucose-based ionic liquids.

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties.

Acridine derivatives have attracted considerable interest in numerous areas owing to their attractive physical and chemical properties. Herein, starting from readily available anthranilic acid, an efficient synthesis of 2,4-bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridine derivatives was accomplished via a one-pot double Sonogashira cross-coupling method. The UV-visible absorption and emission properties of the synthesized molecules have been examined. Additionally, theoretical studies based on density functional theory (DFT/B3LYP/6-31G(d)) were carried out.

Synthesis of novel carbohydrate based pyridinium ionic liquids and cytotoxicity of ionic liquids for mammalian cells.

The large pool of naturally occurring carbohydrates with their diversity in chirality and structure led to the idea of a systematic investigation of carbohydrate based ILs. To this end, we investigated the influence of different ether groups, mainly methyl or ethyl ether, on the secondary OH groups as well as different configurations on physical properties such as melting point, thermostability and especially the influence on cell toxicity. For this investigation we chose α- and ß-methyl-, ß-allyl- and ß-phenyl d-glucopyranose as well as four 1-deoxy-pentoses. In order to be able to classify the results, more ionic liquids with different structural motives were examined for cytotoxicity. Here, we present data that confirm the biocompatibility of such ILs consisting of naturally occurring molecules or their derivatives. The synthesized carbohydrate based ILs were tested for their suitability as additives in coatings for medical applications such as drug-eluting balloons.

Organocatalytic Chlorination of Alcohols by P(III)/P(V) Redox Cycling.

A catalytic system for the chlorination of alcohols under Appel conditions was developed. Benzotrichloride is used as a cheap and readily available chlorinating agent in combination with trioctylphosphane as the catalyst and phenylsilane as the terminal reductant. The reaction has several advantages over other variants of the Appel reaction, e.g., no additional solvent is required and the phosphane reagent is used only in catalytic amounts. In total, 27 different primary, secondary, and tertiary alkyl chlorides were synthesized in yields up to 95%. Under optimized conditions, it was also possible to convert epoxides and an oxetane to the dichlorinated products.

The use of platelet rich plasma, bone morphogenetic protein-2 and different scaffolds in oral and maxillofacial surgery - literature review in comparison with own clinical experience.

OBJECTIVES: The purpose of this article was to review and critically assess the use of platelet rich plasma, recombinant human bone morphogenetic protein-2 and different scaffolds (i.e. tricalciumphosphate, polycaprolactone, demineralized bone matrix and anorganic bovine bone mineral) in oral and maxillofacial surgery comparing the relevant literature and own clinical experience. MATERIAL AND METHODS: A literature review was conducted using MEDLINE, MEDPILOT and COCHRANE DATABASE OF SYSTEMATIC REVIEWS. It concentrated on manuscripts and overviews published in the last five years (2006-2010). The key terms employed were platelet rich plasma, bone morphogenetic proteins and their combinations with the above mentioned scaffolds. The results of clinical studies and animal trials were especially emphasized. The statements from the literature were compared with authors' own clinical data. RESULTS: New publications and overviews demonstrate the advantages of platelet rich plasma in bone regeneration. The results from the literature review were discussed and compared with the publications detailing authors' own experiences. CONCLUSIONS: A favourable outcome concerning newly grown bone was achieved combining platelet rich plasma in addition to optimal matrices with or without recombinant human bone morphogenetic protein-2, depending on the clinical case. As a consequence, the paradigm shift from transplantation of autogenous bone to bone tissue engineering appears promising.

Modern bone regeneration instead of bone transplantation: a combination of recombinant human bone morphogenetic protein-2 and platelet-rich plasma for the vertical augmentation of the maxillary bone-a single case report.

This publication describes the clinical case of a 75-year-old woman. She suffered from total alveolar ridge atrophy due to 20 years of wearing dentures. Bone transplantation, including harvesting of the iliac crest, was rejected by another clinic due to various existing diseases and risk of blood loss on donor side. Moreover, the minimal residual alveolar ridge did not allow bone fixation using screws nor did it allow osteodistraction. Before deciding which bone tissue engineering techniques should best be employed in this surgical treatment, cardiological and internistic consultations and treatments were carried out. In addition, anesthetic preparations were made. The surgical treatment was performed implementing special bridge flap techniques to preserve the periosteum. Tricalcium phosphate blocks soaked with recombinant human bone morphogenetic protein-2 and platelet-rich plasma were implanted on the narrow alveolar ridge. They were attached by tightening the soft tissue, including the periosteum. Four months later, after complication-free wound healing and bone regeneration, six dental implants were inserted into the new alveolar ridge. The histology of all bone samples showed vital lamellar bone. Three months after implantation, a new dental structure was fixed on the implants. The patient's quality of life improved significantly with this new situation.

Mandibular defect reconstruction using three-dimensional polycaprolactone scaffold in combination with platelet-rich plasma and recombinant human bone morphogenetic protein-2: de novo synthesis of bone in a single case.

This publication describes the clinical case of a 71-year-old female patient. Using polycaprolactone (PCL) scaffold, platelet-rich plasma (PRP) and recombinant human bone morphogenetic protein-2 (rhBMP-2), a critical-sized defect in the anterior mandible was regenerated using de novo-grown bone. A bacterial infection had caused a periimplantitis in two dental implants leading to a large destruction in the anterior mandible. Both implants were removed under antibiotic prophylaxis. A PCL scaffold was prepared especially for this clinical case. In a second procedure with antibiotic prophylaxis, the bony defect was reopened. The PCL scaffold was fitted and charged with PRP and rhBMP-2 (1.2 mg). After complication-free wound healing, the radiological control demonstrated de novo-grown bone in the anterior mandible 6 months postoperatively. Dental implants were inserted in a third operation. A bone biopsy of the newly grown bone, as well as of the bordering local bone, was taken and histologically examined. The bone samples were identical and presented vital laminar bone.

De novo grown bone on exposed implant surfaces using photodynamic therapy and recombinant human bone morphogenetic protein-2: case report.

The reconstruction of bone on exposed implant surfaces requires an almost complete elimination of attached bacteria. Only then is new bone growth possible. This case report describes a new way to kill biofilms with photodynamic therapy and to augment bone by using recombinant human bone morphogenetic protein-2. Though the new technique of bone tissue engineering causes some problems, new bone growth on uncovered implant surfaces is successful to a large extent.