- Rotaxane-branched dendrimers with enhanced photosensitization
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During the past few decades, fabrication of functional rotaxane-branched dendrimers has become one of the most attractive yet challenging topics within supramolecular chemistry and materials science. Herein, we present the successful fabrication of a fami
- Li, Wei-Jian,Hu, Zhubin,Xu, Lin,Wang, Xu-Qing,Wang, Wei,Yin, Guang-Qiang,Zhang, Dan-Yang,Sun, Zhenrong,Li, Xiaopeng,Sun, Haitao,Yang, Hai-Bo
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- Synthesis and biological evaluation of bivalent cannabinoid receptor ligands based on hCB2R selective benzimidazoles reveal unexpected intrinsic properties
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The design of bivalent ligands targeting G protein-coupled receptors (GPCRs) often leads to the development of new, highly selective and potent compounds. To date, no bivalent ligands for the human cannabinoid receptor type 2 (hCB2R) of the end
- Nimczick, Martin,Pemp, Daniela,Darras, Fouad H.,Chen, Xinyu,Heilmann, Joerg,Decker, Michael
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- Thiosquaramide-Based Supramolecular Polymers: Aromaticity Gain in a Switched Mode of Self-Assembly
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Despite a growing understanding of factors that drive monomer self-assembly to form supramolecular polymers, the effects of aromaticity gain have been largely ignored. Herein, we document the aromaticity gain in two different self-assembly modes of squara
- Boraghi, Mahsa,Davis, Joyal,Englebienne, Pablo,Gupta, Karthick Babu Sai Sankar,Hagemeijer, Alexander,Kieltyka, Roxanne E.,Lauria, Francesca,Rudge, Raisa,Saez Talens, Victorio,Trinh, Thuat T.,Voets, Ilja K.,Wen, Zhili,Wu, Chia-Hua,Wu, Judy I.
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- Design and synthesis of self-included pillar[5]arene-based bis-[1]rotaxanes
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Two strategies for the design of new pillar[5]arene-based mechanically self-interlocked molecules (MSMs) are reported here. The first strategy is based on the construction of an intermediate pseudo[1]rotaxane followed by the desired bis-[1]rotaxane. The o
- Wang, Mengjun,Du, Xusheng,Tian, Huasheng,Jia, Qiong,Deng, Rong,Cui, Yahan,Wang, Chunyu,Meguellati, Kamel
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- Strategic engineering of alkyl spacer length for a pH-tolerant lysosome marker and dual organelle localization
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Long-term visualization of lysosomal properties is extremely crucial to evaluate diseases related to their dysfunction. However, many of the reported lysotrackers are less conducive to imaging lysosomes precisely because they suffer from fluorescence quenching and other inherent drawbacks such as pH-sensitivity, polarity insensitivity, water insolubility, slow diffusibility, and poor photostability. To overcome these limitations, we have utilized an alkyl chain length engineering strategy and synthesized a series of lysosome targeting fluorescent derivatives namelyNIMCsby attaching a morpholine moiety at theperiposition of the 1,8-naphthalimide (NI) ring through varying alkyl spacers between morpholine and 1,8-naphthalimide. The structural and optical properties of the synthesizedNIMCswere explored by1H-NMR, single-crystal X-ray diffraction, UV-Vis, and fluorescence spectroscopy. Afterward, optical spectroscopic measurements were carefully performed to identify a pH-tolerant, polarity sensitive, and highly photostable fluoroprobes for further live-cell imaging applications.NIMC6displayed excellent pH-tolerant and polarity-sensitive properties. Consequently, allNIMCswere employed in kidney fibroblast cells (BHK-21) to investigate their applicability for lysosome targeting and probing lysosomal micropolarity. Interestingly, a switching of localization from lysosomes to the endoplasmic reticulum (ER) was also achieved by controlling the linker length and this phenomenon was subsequently applied in determining ER micropolarity. Additionally, the selected probeNIMC6was also employed in BHK-21 cells for 3-D spheroid imaging and inCaenorhabditis elegans(C. elegans) forin vivoimaging, to evaluate its efficacy for imaging animal models.
- Bhowal, Rohit,Biswas, Suprakash,Chopra, Deepak,Dutta, Tanoy,Koner, Apurba L.,Silswal, Akshay
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p. 9630 - 9644
(2021/07/28)
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- Artificial Light-Harvesting Systems Based on AIEgen-branched Rotaxane Dendrimers for Efficient Photocatalysis
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Aiming at the construction of novel platform for efficient light harvesting, the precise synthesis of a new family of AIEgen-branched rotaxane dendrimers was successful realized from an AIEgen-functionalized [2]rotaxane through a controllable divergent ap
- Hu, Yi-Xiong,Li, Wei-Jian,Wang, Wei,Wang, Xu-Qing,Xu, Lin,Xu, Wei-Tao,Yang, Hai-Bo,Zhang, Dan-Yang
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supporting information
p. 18761 - 18768
(2021/07/20)
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- Reversible diels–alder reactions with a fluorescent dye on the surface of magnetite nanoparticles
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Diels–Alder reactions on the surface of nanoparticles allow a thermoreversible functionalization of the nanosized building blocks. We report the synthesis of well-defined magnetite nanoparticles by thermal decomposition reaction and their functionalizatio
- He, Siyang,Kickelbick, Guido
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- Identifying Structural Determinants of Mesomorphism from Focused Libraries of Tripedal Mesogens Prepared via the Passerini Three-Component Reaction
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Heterolithic tripedal mesogens are branched, multifunctional molecules that exhibit liquid crystalline properties. The liquid crystalline phase behavior of heterolithic tripedal mesogens can be challenging to predict from the structures of the different branches. To elucidate the structural basis for smectic mesomorphism in the first examples of heterolithic ABC tripedal mesogens, we synthesized and characterized six homolithic, three heterolithic AB2, and seven heterolithic ABC tripedes. The synthesis strategy took advantage of the Passerini three-component reaction to elaborate focused compound libraries in a combinatorial and high throughput manner. The phase behavior of the tripedes was characterized by a combination of polarized optical microscopy (POM), differential scanning calorimetry (DSC), and powder X-ray diffraction techniques. We show that one end-group of the heterolithic mesogens is responsible for the emergence of smectic mesomorphism in the presence of other groups that prefer nematic mesomorphism. Understanding how these structurally complex, non-conventional mesogens self-organize in liquid crystalline mesophases is significant for designing functional materials with predictable hierarchical order.
- Song, Shuang,Sahoo, Dipankar,Kumar, Manoj,Barkley, Deborah A.,Heiney, Paul A.,Rudick, Jonathan G.
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supporting information
p. 1195 - 1207
(2019/01/04)
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- Construction of type iii-c rotaxane-branched dendrimers and their anion-induced dimension modulation feature
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Starting from a novel rotaxane building block with dendrimer growth sites being located at both the wheel and axle component, we realized the successful construction of a new family of rotaxane-branched dendrimers, i.e., Type III-C rotaxane-branched dendr
- Wang, Xu-Qing,Li, Wei-Jian,Wang, Wei,Wen, Jin,Zhang, Ying,Tan, Hongwei,Yang, Hai-Bo
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supporting information
p. 13923 - 13930
(2019/09/30)
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- Highly Selective Butyrylcholinesterase Inhibitors with Tunable Duration of Action by Chemical Modification of Transferable Carbamate Units Exhibit Pronounced Neuroprotective Effect in an Alzheimer's Disease Mouse Model
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In this study, the carbamate structure of pseudo-irreversible butyrylcholinesterase (BChE) inhibitors was optimized with regard to a longer binding to the enzyme. A set of compounds bearing different heterocycles (e.g., morpholine, tetrahydroisoquinoline, benzimidazole, piperidine) and alkylene spacers (2 to 10 methylene groups between carbamate and heterocycle) in the carbamate residue was synthesized and characterized in vitro for their binding affinity, binding kinetics, and carbamate hydrolysis. These novel BChE inhibitors are highly selective for hBChE over human acetycholinesterase (hAChE), yielding short-, medium-, and long-acting nanomolar hBChE inhibitors (with a half-life of the carbamoylated enzyme ranging from 1 to 28 h). The inhibitors show neuroprotective properties in a murine hippocampal cell line and a pharmacological mouse model of Alzheimer's disease (AD), suggesting a significant benefit of BChE inhibition for a disease-modifying treatment of AD.
- Hoffmann, Matthias,Stiller, Carina,Endres, Erik,Scheiner, Matthias,Gunesch, Sandra,Sotriffer, Christoph,Maurice, Tangui,Decker, Michael
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p. 9116 - 9140
(2019/11/03)
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- Design, synthesis and insecticide activity of novel acetylcholinesterase inhibitors: Triazolinone and phthalimide heterodimers
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Based on the “cluster effect” and the structure characters of acetylcholinesterase (AChE; EC 3.1.1.7), a new series of 1,2,4-triazolin-3-one and phthalimide heterodimers were designed, synthesized, and evaluated as potent dual acetylcholinesterase inhibitors (AChEIs). Most of the synthesized compounds showed good in vitro inhibitory activities towards both Drosophila melanogaster acetylcholinesterase (DmAChE) and Musca domestica acetylcholinesterase (MdAChE). Among them, 5g was found to be the most potent anti-AChE de-rivate (5g, IC50=8.07μM to DmAChE, IC50=32.24μM to MdAChE). It was 2.31- and 1.35-fold more active than the positive control ethion (CP, IC50=18.62μM to DmAChE, IC50=43.56μM to MdAChE). The docking model study revealed that 5g possessed the fitted spatial structure and bound to the central pocket and peripheral site of DmAChE. Moreover, most compounds demonstrated high insecticidal activity to Lipaphis erysimi and Tetranychus cinnabarinus at the concentration of 300mg/L.
- Xie, Ruliang,Mei, Xiangdong,Ning, Jun
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p. 345 - 350
(2019/05/07)
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- HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC CONDITIONS AND DISORDERS
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The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): (I), wherein L1, A, X1, X2, R1, R2, and R3 are described herein.
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Page/Page column 367; 368
(2018/03/25)
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- Microorganism detection and analysis using carbohydrate and lectin recognition
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Methods of binding and detecting a microorganism on a solid substrate. The microorganism is bound on a solid substrate covalently bound to a capture agent having a saccharide moiety. A lectin capable of binding to the microorganism and the saccharide moiety of the capture agent is added to the sample to bind the microorganism on the solid substrate. Further provided are biosensor devices, such as a quartz crystal microbalance (QCM) device or a surface plasmon resonance (SPR) device, that incorporate the solid substrate for the detection of microorganisms.
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Sheet 23 of 24
(2016/09/26)
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- Chemical engineering of donor-acceptor liquid crystalline dyads and triads for the controlled nanostructuration of organic semiconductors
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Multi-segregated columnar structures provide a geometrically ideal scheme for ambipolar organic semiconductors, but are not easy to design. A set of novel materials with dyad and triad architectures based on 2 different discotic cores is reported and the conditions of emergence of such complex structures are investigated. The designed molecules associate together electron-donor triphenylene cores (D) and perylene or naphthalene diimides as acceptor moieties (A), both entities being linked via alkyl chain spacers. The evaluation in solution of their HOMO/LUMO energy levels by cyclic voltammetry demonstrates the preservation of the individual features of the D and A units. Their thermal and self-organization behaviors were studied by polarized-light optical microscopy, differential scanning calorimetry, temperature-dependent small-angle X-ray scattering and dilatometry, which permitted detailed investigation of the self-organization behaviour. These D-A compounds turned out to spontaneously self-organize into columnar mesophases at room temperature, with the D and A moieties segregated into either alternated stacks within mixed columns or in distinct columns, the latter providing an ideal configuration for 1D hole and electron transport pathways. In view of potential applications of the triad/dyad template, thin films of these self-organized materials were also probed by atomic force microscopy and grazing incidence X-ray scattering.
- Xiao, Yiming,Su, Xiaolu,Sosa-Vargas, Lydia,Lacaze, Emmanuelle,Heinrich, Beno?t,Donnio, Bertrand,Kreher, David,Mathevet, Fabrice,Attias, André-Jean
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p. 4787 - 4798
(2016/07/06)
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- Design, synthesis and bioactivity of novel phthalimide derivatives as acetylcholinesterase inhibitors
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A series of novel phthalimide derivatives related to benzylpiperazine were synthesized and evaluated as cholinesterase inhibitors. The results showed that all compounds were able to inhibit acetylcholinesterase (AChE), with two of them dramatically inhibiting butyrylcholinesterase (BuChE). Most compounds exhibited potent anti-AChE activity in the range of nM concentrations. In particular, compounds 7aIII and 10a showed the most potent activity with the IC50 values of 18.44 nM and 13.58 nM, respectively. To understand the excellent activity of these compounds, the structure-activity relationship was further examined. The protein-ligand docking study demonstrated that the target compounds have special binding modes and these results are in agreement with the kinetic study.
- Si, Weijie,Zhang, Tao,Zhang, Lanxiang,Mei, Xiangdong,Dong, Mengya,Zhang, Kaixin,Ning, Jun
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supporting information
p. 2380 - 2382
(2016/04/20)
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- Phosphonium lipocations as antiparasitic agents
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Phosphonium lipocations were synthesized and evaluated for inhibition of the development of Plasmodium falciparum and Trypanosoma cruzi, etiological agents of malaria and Chagas disease, respectively. Optimal phthalimides and 1,4-naphthoquinone-based lipocations were active in vitro at mid-high nM concentrations against P. falciparum and low μM concentrations against T. cruzi.
- Long, Timothy E.,Lu, Xiao,Galizzi, Melina,Docampo, Roberto,Gut, Jiri,Rosenthal, Philip J.
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scheme or table
p. 2976 - 2979
(2012/06/04)
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- SMALL-MOLECULE BOTULINUM TOXIN INHIBITORS
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This disclosure relates to materials and methods for inhibiting Botulinum neurotoxin, and more particularly to materials and methods for inhibiting the zinc endopeptidase of Botulinum neurotoxin serotypes A, D and/or E (BoNTA, BoNTD and/or BoNTE).
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- Rapid Synthesis of New DNMT Inhibitors Derivatives of Procainamide
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DNA methyltransferases (DNMTs) are responsible for DNA methylation, an epigenetic modification involved in gene regulation. Families of conjugates of procainamide, an inhibitor of DNMT1, were conceived and produced by rapid synthetic pathways. Six compoun
- Halby, Ludovic,Champion, Christine,Senamaud-Beaufort, Catherine,Ajjan, Sophie,Drujon, Thierry,Rajavelu, Arumugam,Ceccaldi, Alexandre,Jurkowska, Renata,Lequin, Olivier,Nelson, William G.,Guy, Alain,Jeltsch, Albert,Guianvarc'h, Dominique,Ferroud, Clotilde,Arimondo, Paola B.
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experimental part
p. 157 - 165
(2012/04/17)
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- A mesogenic triphenylene-perylene-triphenylene triad
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A straightforward synthesis of triphenylene-perylene-triphenylene triad structures has been achieved by using versatile triphenylene intermediates bearing a single oxyalkyl amine side chain. Among these, PBITP10 showed a stable columnar mesophase implying favorably matched core-core separations in the structure. Importantly, the triad can be used as a vehicle for doping columnar triphenylene matrices with functional but incompatible perylene units and a mixture of hexahexyloxytriphenylene matrix doped with 0.1% PBITP10 is homogeneous and liquid crystalline.
- Kong, Xiangfei,He, Zhiqun,Zhang, Yinning,Mu, Linping,Liang, Chunjun,Chen, Bo,Jing, Xiping,Cammidge, Andrew N.
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p. 764 - 767
(2011/04/24)
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- Synthesis of disulfides containing a corrinoid head group for preparation of self-assembled monolayers
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The synthesis of three novel alkane disulfides with head-groups derived from vitamin B12, 14a, 14b and 15, is described. Self-assembled monolayers on gold are prepared from the symmetrical disulfide 15, bearing two cobyrinate head groups. The coating of the gold surface is analyzed by TOF-SIMS and ESCA measurements. Georg Thieme Verlag Stuttgart.
- Mendon?a, Joana,Luginbühl, Reto,Siegenthaler, Hans,Keese, Reinhart
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p. 1901 - 1904
(2007/10/03)
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- Separation of lanthanides and actinides using magnetic silica particles bearing covalently attached tetra-CMPO-calix[4] arenes
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Calix[4]arene tetraethers in the cone conformation bearing four -NH-CO-CH2-P(O)Ph2 (= CMPO) residues on their wide rim and one, two or four ω-amino alkyl residues of various lengths at the narrow rim were synthesized. Reaction with dichlorotriazinyl (DCT) functionalized magnetic particles led to complete coverage of the available surface by covalently linked CMPO-calix[4]arenes in all cases. Magnetically assisted removal of Eu(III) and Am(III) from acidic solutions was distinctly more efficient with these particles in comparison to analogous particles bearing the same amount of analogous single-chain CMPO-functions. The best result, an increase of the extraction efficiency by a factor of 140-160, was obtained for attachment via two propyl spacers. The selectivity Am/Eu was in the range of 1.9-2.8. No decrease of the extraction ability was observed, when the particles were repeatedly used, after simple back extraction with water.
- Boehmer, Volker,Dozol, Jean-Francois,Gruettner, Cordula,Liger, Karine,Matthews, Susan E.,Rudershausen, Sandra,Saadioui, Mohamed,Wang, Pingshan
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p. 2327 - 2334
(2007/10/03)
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- Search for histamine H3 receptor ligands with combined inhibitory potency at histamine N-methyltransferase: ω- piperidinoalkanamine derivatives
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In an effort to design new hybrid compounds with dual properties, i.e. binding affinity at histamine H3 receptors and inhibitory potency at the catabolic enzyme histamine Nτ-methyltransferase (HMT), a novel series of 1-substituted piperidine derivatives was synthesized. This alicyclic heterocycle is structurally linked via aminoalkyl spacers of variable lengths to additional aromatic carbo- or heterocycles. These new hybrid drugs were pharmacologically evaluated regarding their binding affinities at recombinant human H3 receptors, stably expressed in CHO cells, and in a functional assay for their inhibitory potencies at rat kidney HMT. All compounds investigated proved to be H3 receptor ligands with binding affinities in the micro- to nanomolar concentration range despite significant differences in the type of the aromatic moiety introduced. The most potent compound in this series was the quinoline derivative 20 (Ki = 5.6 nM). Likewise, all new ligands studied showed impressive HMT inhibitory activities. Here, compounds 5, 10, 14, and 18-20 exhibited submicromolar potencies (IC50 = 0.061 -0.56 μM). The aminomethylated quinoline 19 showed almost the same, well balanced nanomolar activities on both targets. In this study, new hybrid compounds with a dual mode biological action were developed. These pharmacological agents are valuable leads for further development and candidates for treatment of histamine-dependent disorders.
- Grassmann, Sven,Apelt, Joachim,Ligneau, Xavier,Pertz, Heinz H.,Arrang, Jean-Michel,Ganellin, C. Robin,Schwartz, Jean-Charles,Schunack, Walter,Stark, Holger
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p. 533 - 545
(2007/10/03)
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- Development of a new class of nonimidazole histamine H3 receptor ligands with combined inhibitory histamine N-methyltransferase activity
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In search of novel ways to enhance histaminergic neurotransmission in the central nervous system, a new class of nonimidazole histamine H3 receptor ligands were developed that simultaneously possess strong inhibitory activity on the main histamine metabolizing enzyme, histamine N-methyltransferase (HMT). The novel compounds contain an aminoquinoline moiety, which is an important structural feature for HMT inhibitory activity, connected by different spacers to a piperidino group (for H3 receptor antagonism). Variation of the spacer structure provides two different series of compounds. One series, having only an alkylene spacer between the basic centers, led to highly potent HMT inhibitors with moderate to high affinity at human histamine H3 receptors. The second series possesses a p-phenoxypropyl spacer, which may be extended by another alkylene chain. This latter series also showed strong inhibitory activity on HMT, and in most cases, the H3 receptor affinity even surpassed that of the first series. One of the most potent compounds with this dual mode of action is 4-(4-(3-piperidinopropoxy)phenylamino)quinoline (34) (hH3, Ki = 0.09 nM; HMT, IC50 = 51 nM). This class of compounds showed high antagonist potency and good H3 receptor selectivity in functional assays in guinea pig on H1, H2, and H3 receptors. Because of low or missing in vivo activity of two selected compounds, the proof of concept of these valuable pharmacological tools for the supposed superior overall enhancing effect on histaminergic neurotransmission failed to appear hitherto.
- Apelt, Joachim,Ligneau, Xavier,Pertz, Heinz H.,Arrang, Jean-Michel,Ganellin, C. Robin,Schwartz, Jean-Charles,Schunack, Walter,Stark, Holger
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p. 1128 - 1141
(2007/10/03)
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- Synthesis of ω-substituted alkanethiols and (bromomethyl)methylthiomalonates
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Several multifunctional derivatives of methylthiomalonic acid (= 2-(thiocarboxy)acetic acid), i.e. 20a,b, 21, 22a,b, and 24, were prepared from thiols bearing a functionalized head group, i.e. from 9a,b, 12, and 16d,f (Schemes 4 and 5). The association constants of the two dithio podands 8b and 11 with K+ were determined.
- Pfammatter, Michael J.,Siljegovic, Vuk,Darbre, Tamis,Keese, Reinhart
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p. 678 - 689
(2007/10/03)
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- Rapid synthesis of large enaminolactams, a novel class of macrocycles
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An efficient preparation of enaminolactams using an original synthetic method based on the thermal decomposition of Meldrum's acids derivatives is reported. The key step involves an intramolecular addition of ω-aminoalkyl- aminomethyleneketenes.
- Jourdain, Franck,Caron, Mireille,Pommelet, Jean Claude
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p. 1785 - 1799
(2007/10/03)
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- Potent acetylcholinesterase inhibitors: Design, synthesis, and structure - Activity relationships of bis-interacting ligands in the galanthamine series
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New galanthamine derivatives, especially bis-interacting ligands 3-5 and 7-9 were prepared in order to interact with the catalytic and the peripheral sites of acetylcholinesterase (AChE). The synthesis, the anticholinesterase activities, and the structure-activity relationships of bis-interacting ligands are reported. Compounds 4d-e were found to be more potent than galanthamine and tacrine in inhibiting AChE. Copyright (C) 1998 Elsevier Science Ltd.
- Mary, Aude,Renko, Dolor Zafiarisoa,Guillou, Catherine,Thal, Claude
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p. 1835 - 1850
(2007/10/03)
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- Synthesis and activity studies of N-[ω-N'-(adamant-1'-yl)aminoalkyl]-2-(4'-dimethylaminophenyl)acetamides: In the search of selective inhibitors for the different molecular forms of acetylcholinesterase
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A series of N-[ω-N'-(adamant-1'-yl)aminoalkyl]-2-(4'-dimethylaminophenyl)acetamides were synthesized and tested as acetylcholinesterase inhibitors. A significant selectivity toward acetylcholinesterases from various natural sources, mainly differing in th
- Perola, Emanuele,Cellai, Luciano,Brufani, Mario
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p. 575 - 580
(2007/10/03)
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- 3-heteroalkyl-2,4.quinzaoline-diones
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A compound is described which is selected from the group consisting of those of the formula: wherein A is a divalent moiety of the formula:, -CnH2n- -CH2CH=CHCH2- or and n is an integer from 2-10, inclusive;, R is hydrogen, oxygen or alkyl having from one to four carbon atoms;, Z is C or N; and when, Z is N, ---is when, Z is C and R is oxygen, ---is ―――; and when, Z is C and R is alkyl, ---is R6 is hydrogen or alkyl having from one to four carbon atoms;, R1 and R2 may be the same or different and may be selected from the group consisting of hydrogen, halogen, trifluoromethyl, alkoxy having from one to four carbon atoms, alkyl having from one to four carbon atoms, nitro and amino; wherein Heteroaryl is wherein R3 and R4 may be selected from hydrogen, alkyl having from one to four carbon atoms, or phenyl; and, X is CH or N, together with the pharmaceutically acceptable salts thereof as well as a process for producing the same and its use for pharmaceutical processes.
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- 3-heteroalkyl-2,4-quinzaolinediones
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Compounds of the formula: STR1 wherein A is a divalent moiety of the formula: or STR2 wherein n is an integer from 2-10, inclusive; R is hydrogen or alkyl having from one to four carbon atoms; R1 and R2 may be the same or different and may be selected from the group consisting of hydrogen, halogen, trifluoromethyl, alkoxy having from one to four carbon atoms, alkyl having from one to four carbon atoms, nitro and amino; wherein Heteroaryl is STR3 wherein R3 and R4 may be selected from hydrogen, alkyl having from one to four carbon atoms, or phenyl; and X is CH or N, together with the pharmaceutically acceptable salts thereof, which act as thromboxane synthetase inhibitors and hypotensive agents; methods for their production and use.
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- 3-heteroarylalkyl-4-quinazolinones
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Novel 3-heteroarylalkyl-4-quinazolinones which are useful as inhibitors of thromboxane synthetase and/or as antihypertensive agents in the treatment of hypertension and myocardial ischemia.
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- Photoresponsive Crown Ethers. Part 14. Photoregulated Crown-Metal Complexation by Competitive Intramolecular Tail(Ammonium)-biting
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New photoresponsive crown ethers (1H+) having a crown ether ring and an ammoniumalkyl +-(CH2)n, n = 4,6,10> group attached to the two sides of an azobenzene have been synthesized.These photoresponsive 'tail-biting' crown ethers have been designed so that intramolecular 'biting' of the ammonium group to the crown can only occur upon photoisomerisation to the cis-forms.In the thermal cis-trans isomerisation, the first-order rate constants for cis-(1H+) were smaller by 1.6 - 2.2 -fold than those for (1) (the analogous free amines).Moreover, this rate increased with increasing added K+ concentration.This suggests that the ammonium tail is intramolecularly bound to the crown ether ring in cis-(1H+).This intramolecular 'biting' is further reflected in the relative affinities of (1H+) for alkali-metal cations.The affinities were markedly reduced by u.v.-light irradiation and in particular, cis-(1H+)(n=6) and cis-(1H+)(n=10) showed almost no metal-binding ability.This marked difference in the metal-binding ability was used to generate the light-controlled systems for the passive or active ion-transport of ions across a liquid membrane.
- Shinkai, Seiji,Ishihara, Midori,Ueda, Kaori,Manabe, Osamu
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p. 511 - 518
(2007/10/02)
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