- Predictable adjustment of spin crossover temperature in solutions of iron(III) complexes functionalized with alkyl-urea tails
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A new series of amphiphilic alkylurea functionalised iron(III) sal2trien complexes were prepared by substitution of phenolic ligand site with OCnH2n-NHC(=O)NHCmH2m+1 tails (n = 5, 9, m = 4, 12, 14, 16). These complexes display remarkably tunable spin-crossover (SCO) behaviour in solution. By imposing very slight structural modifications in the number of methylene recognition sites in a position remote from the functional unit, i.e. the SCO active iron(III) centre, the transition temperature T1/2 is modulated in a predictable manner. Additionally, a correlation between the concentration of the SCO-active amphiphile and its T1/2 allows for precise fine-tuning of the spin-transition properties and for quantifying the efficiency of self-assembly.
- Johnson, Chloe J.,Morgan, Grace G.,Albrecht, Martin
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Read Online
- Direct and Enantioselective Aldol Reactions Catalyzed by Chiral Nickel(II) Complexes
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A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes is reported. The reaction gives the corresponding O-TIPS-protected anti-aldol adducts in high yields and with remarkable stereocontrol and atom economy. Furthermore, the straightforward removal of the achiral scaffold provides enantiomerically pure intermediates of synthetic interest, which involve precursors for anti-α-amino-β-hydroxy and α,β-dihydroxy carboxylic derivatives. Theoretical calculations explain the observed high stereocontrol.
- Kennington, Stuart C. D.,Teloxa, Saul F.,Mellado-Hidalgo, Miguel,Galeote, Oriol,Puddu, Sabrina,Bellido, Marina,Romea, Pedro,Urpí, Fèlix,Aullón, Gabriel,Font-Bardia, Mercè
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Read Online
- A series of novel, potent, and selective histone deacetylase inhibitors
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Histone deacetylase (HDAC) inhibitors offer a promising strategy for cancer therapy and the first generation HDAC inhibitors are currently in clinical trials. A structurally novel series of HDAC inhibitors based on the natural cyclic tetrapeptide Apicidin is described. Selected screening of the sample collection looking for L-2-amino-8-oxodecanoic acid (L-Aoda) derivatives identified a small acyclic lead molecule 1 with the unusual ketone zinc binding group. SAR studies around this lead resulted in optimization to potent, low molecular weight, selective, non-hydroxamic acid HDAC inhibitors, equipotent to current clinical candidates.
- Jones, Philip,Altamura, Sergio,Chakravarty, Prasun K.,Cecchetti, Ottavia,Francesco, Raffaele De,Gallinari, Paola,Ingenito, Raffaele,Meinke, Peter T.,Petrocchi, Alessia,Rowley, Michael,Scarpelli, Rita,Serafini, Sergio,Steinkuehler, Christian
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Read Online
- Radial control of recognition and redox processes with multivalent nanoparticle hosts
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Mixed Monolayer Protected Gold Clusters (MMPCs) featuring both hydrogen bonding and aromatic stacking molecular recognition functionalities have been used to create multivalent hosts for flavins. Multitopic binding of these hosts to flavin was shown to have a strong radial dependence: when the recognition site was brought closer to the MMPC surface, recognition was enhanced ~3-fold due to increased preorganization. The effect of preorganization is reversed upon reduction of flavin, where the MMPC with longer side chains bind the flavin guest ~7-fold stronger than the short chain counterpart due to unfavorable dipolar interactions between the electron-rich aromatic stacking units of the host and the anionic flavin guest. This fine-tuning of recognition and redox processes provides both a model for enzymatic systems and a tool for the fabrication of devices.
- Boal, Andrew K.,Rotello, Vincent M.
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Read Online
- Constitutional Dynamic Selection at Low Reynolds Number in a Triple Dynamic System: Covalent Dynamic Adaptation Driven by Double Supramolecular Self-Assembly
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A triple dynamic complex system has been designed, implementing a dynamic covalent process coupled to two supramolecular self-assembly steps. To this end, two dynamic covalent libraries (DCLs), DCL-1 and DCL-2, have been established on the basis of dynamic covalent C-C/C-N organo-metathesis between two Knoevenagel derivatives and two imines. Each DCL contains a barbituric acid-based Knoevenagel constituent that may undergo a sequential double self-organization process involving first the formation of hydrogen-bonded hexameric supramolecular macrocycles that subsequently undergo stacking to generate a supramolecular polymer SP yielding a viscous gel state. Both DCLs display selective self-organization-driven amplification of the constituent that leads to the SP. Dissociation of the SP on heating causes reversible randomization of the constituent distributions of the DCLs as a function of temperature. Furthermore, diverse distribution patterns of DCL-2 were induced by modulation of temperature and solvent composition. The present dynamic systems display remarkable self-organization-driven constitutional adaption and tunable composition by coupling between dynamic covalent component selection and two-stage supramolecular organization. In more general terms, they reveal dynamic adaptation by component selection in low Reynolds number conditions of living systems where frictional effects dominate inertial behavior.
- Gu, Ruirui,Lehn, Jean-Marie
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supporting information
p. 14136 - 14146
(2021/09/15)
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- Lipophilic fluorescein probe and preparation method thereof
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The invention relates to the field of lipophilic fluorescein probes, and particularly discloses a lipophilic fluorescein probe and a preparation method thereof. The lipophilic fluorescein probe according to the present application is represented by the following chemical formula 1, wherein R is a C1-C20 alkylene group or cycloalkylene group; and R' is C1-C20 alkyl, cycloalkyl, aralkyl, arcycloalkyl, alkaryl or naphthenic aryl. The lipophilic fluorescein probe is high in stability and not prone to self-hydrolysis, fluorescein can be released through rapid hydrolysis under the action of lipase, and therefore the lipophilic fluorescein probe has very high affinity acting force and very low detection limit on the lipase. In addition, the preparation method disclosed by the invention is simple to operate and high in yield .
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Paragraph 0060; 0063
(2021/04/21)
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- Gemfibrozil derivatives as activators of soluble guanylyl cyclase – A structure-activity study
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Previous studies demonstrated that anti-hyperlipidemic drug gemfibrozil acts as NO- and heme-independent activator of NO receptor soluble guanylyl cyclase. A series of new gemfibrozil derivatives were synthesized and evaluated for sGC activation. The structure-activity relationship study identified the positions in gemfibrozil's scaffold that are detrimental for sGC activation and those that are amendable for optimizing modifications. Compared with gemfibrozil, compounds 7c and 15b were more potent activators of cGMP-forming activity of purified sGC and exhibited enhanced relaxation of preconstricted mouse thoracic aorta rings. These studies established the overall framework needed for futher improvement of sGC activators based on gemfibrozil scaffold.
- Baker, Hannah,Ferreira, Liam D.,Gayler, Kevin M.,Kane, Robert R.,Karunananthan, Johann W.,Kostyo, Jessica H.,Martin, Emil,Mattke, Jordan,Nguyen, Harold,Plunk, Michael A.,Quintana, Jeremy M.,Sharina, Iraida,Shuda, Mina,Stinchcomb, Alexandra L.
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- Synthesis of N-trifluoromethyl amides from carboxylic acids
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Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.
- Flavell, Robert R.,Liu, Jianbo,Parker, Matthew F. L.,Toste, F. Dean,Wang, Sinan,Wilson, David M.
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supporting information
p. 2245 - 2255
(2021/08/12)
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- New desulfured troglitazone derivatives: Improved synthesis and biological evaluation
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Breast cancer is a major medical threat which cannot be sufficiently addressed by current therapies because of spontaneous or acquired treatment resistance. Besides, triple-negative breast cancer (TNBC) tumors do not respond to targeted therapies, thus new therapeutic strategies are needed. In this context, we designed and prepared new desulfured troglitazone (TGZ)-derived molecules and evaluated them in vitro for their anti-proliferative activity, with a special focus on triple-negative breast cancer cell lines. Optimization of the synthetic strategies and deracemization of the lead compound were performed to give highly active compound 10 with low-micromolar potency. Further studies revealed that this compound triggers apoptosis rather than cell cycle arrest as observed with TGZ.
- Dupommier, Dorian,Muller, Claire,Comoy, Corinne,Mazerbourg, Sabine,Bordessa, Andrea,Piquard, Eline,Pawlak, Manon,Piquard, Flavian,Martin, Hélène,De Fays, Elia,Grandemange, Stéphanie,Flament, Stéphane,Boisbrun, Michel
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- Nickel-Catalyzed Cross-Coupling of Alkyl Carboxylic Acid Derivatives with Pyridinium Salts via C-N Bond Cleavage
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The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.
- Pulikottil, Feba Thomas,Pilli, Ramadevi,Suku, Rohith Valavil,Rasappan, Ramesh
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supporting information
p. 2902 - 2907
(2020/04/09)
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- PRODRUGS OF CGRP ANTAGONISTS
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Disclosed are prodrugs of CGRP antagonists, methods of treating CGRP related disorders, e.g., migraine, by administering to a patient in need thereof the prodrugs, pharmaceutical compositions comprising prodrugs and kits including the pharmaceutical compositions and instructions for use.
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Page/Page column 132
(2020/05/19)
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- Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters
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We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.
- Lee, Minhan,Jung, Hoimin,Kim, Dongwook,Park, Jung-Woo,Chang, Sukbok
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supporting information
p. 11999 - 12004
(2020/08/06)
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- Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines
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The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.
- Wang, Yiqiong,Huang, Fei,Zhang, Songlin
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supporting information
p. 5178 - 5181
(2020/08/13)
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- IRAK DEGRADERS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 2062; 2063
(2019/07/10)
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- Highly frustrated liquid crystal phases in optically active dimers: Synthesis and rich phase transitional behavior
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Herein we report on the synthesis and characterization of four new series of optically active, nonsymmetric dimers in which cholesterol is covalently linked to a Schiff base core through an ω-oxyalkanoyl spacer. While the Schiff base core is substituted with n-butyloxy, n-hexyloxy, n-octyloxy, n-decyloxy and n-dodecyloxy tails, three even-parity spacers, namely, 4-oxybutanoyl, 6-oxyhexanoyl, 8-oxyoctanoyl, and an odd-parity spacer, namely, 5-oxypentanoyl, have been used to join the two cores. The experimental results show that the length and parity of the spacer and the length of the terminal tail play a vital role in deciding the phase sequences of the dimers. In general, the dimers possessing an even-parity spacer display enantiotropic LC phases such as chiral nematic (N?), twist grain boundary (TGB), smectic A (SmA), chiral smectic C (SmC?) and twist grain boundary phase with SmC? slabs (TGBC?). Some of these dimers display TGBC? over a wide temperature range. The dimers with an odd-parity (5-oxypentanoyl) spacer display, unlike their even-membered counterparts, blue phases (BPIII/II/I); besides, they stabilize N? and/or unknown smectic (SmX) phases. The circular dichroism (CD) measurements were carried out as a function of temperature on the planar texture formed by three even-membered dimers and an odd-membered dimer. The occurrence of a strong negative CD band in the N? phase of the even-membered dimers suggests a left-handed screw sense of the macroscopic helical structure, and the scenario is opposite in the case of an odd-membered dimer.
- Nayak, Rashmi Ashwathama,Bhat, Sachin A.,Shanker,Rao, D. S. Shankar,Yelamaggad
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supporting information
p. 2148 - 2162
(2019/02/05)
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- Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification
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Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
- Groendyke, Brian J.,Modak, Atanu,Cook, Silas P.
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p. 13073 - 13091
(2019/10/10)
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- Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines
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A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.
- Huang, Fei,Zhang, Songlin
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supporting information
p. 7430 - 7434
(2019/10/11)
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- METHOD
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The invention provides mitochondria-targeted chemiluminescent agents and their use in methods of photodynamic therapy (PDT). In particular, the invention provides compounds of general formula (I), and their pharmaceutically acceptable salts: (I) in which A represents a chemiluminescent moiety; each L, which may be the same or different, is either a direct bond or a linker; each B, which may be the same or different, represents a mitotropic moiety; n is an integer from 1 to 3, preferably 1; and x is an integer from 1 to 3, preferably 1. Such compounds find particular use in the treatment of deeply- sited tumours, e.g. glioblastoma multiforme (GBM), when used in combination with a photosensitizer or photosensitizer precursor.
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Page/Page column 34
(2020/01/11)
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- Discovery of Wogonin-based PROTACs against CDK9 and capable of achieving antitumor activity
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Wogonin is a natural product isolated from the Scutellaria baicalensis and has been proved to be a potent and selective inhibitor of CDK9. Using this scaffold, we designed and synthesized a series of proteolysis targeting chimeras (PROTACs) targeting CDK9 by recruiting ubiquitin E3 ligase cereblon (CRBN). For constructing diverse Wogonin-based PROTACs, a “click chemistry” approach was employed for the synthesis of CDK9-targeting PROTACs. The results of western blotting assays showed that compounds containing triazole group in the linker could selectively downregulate the intracellular CDK9 level. Among these compounds, 11c could selectively degrade CDK9 in a concentration-dependent manner. In addition, the application of the proteasome inhibitor MG132 and CRBN siRNA silencing confirmed that 11c could promote the proteasome-dependent and CRBN-dependent degradation. Consistent with the degradation of the CDK9 protein, 11c selectively inhibits proliferation of CDK9-overexpressed cancer cells. Thus, our Wogonin-based PROTAC would be an efficient probe that induces the degradation of CDK9.
- Bian, Jinlei,Ren, Jie,Li, Yongren,Wang, Jubo,Xu, Xi,Feng, Yifan,Tang, Hui,Wang, Yajing,Li, Zhiyu
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p. 373 - 381
(2018/10/08)
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- LIPID DELIVERY OF THERAPEUTIC AGENTS TO ADIPOSE TISSUE
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A method of treating a disease mediated by protein expression in adipose tissue by intraperitoneally administering a composition comprising a lipid nanoparticle encapsulating or associated with a therapeutic agent (e.g., a nucleic acid), thereby delivering the therapeutic agent to adipose tissue of the subject and altering protein expression in the adipose tissue is provided herein. A method for delivering a therapeutic agent to adipose tissue of a subject in need thereof is also provided.
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Page/Page column 166
(2018/11/10)
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- Preparation method and application of technetium-99m-labeled triphenylphosphine derivative
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The invention relates to a preparation method and application of a technetium-99m-labeled triphenylphosphine derivative and can effectively solve problems of preparation of the triphenylphosphine derivative and use for a cationic myocardial imaging agent. The preparation method comprises the following steps: reacting omega-brominated aliphatic acid I to obtain omega-brominated aliphatic acyl chloride II, and enabling the omega-brominated aliphatic acyl chloride II to react with ferrocene to generate an intermediate III in which the chlorine is substituted by the ferrocene; enabling the intermediate III to react with triphenylphosphine and obtaining a solid product precursor IV through separation; adding a Na99mTcO4 leacheate with a radioactive activity of 740 MBq in a polytetrafluorine high-pressure tank, blow-drying with N2, adding the product precursor, Cr(CO)6, CrCL3 and methanol and sealing the polytetrafluorine high-pressure tank; performing magnetic stirring under an oil bath, then taking an ice bath, filtering, purifying a filtrate with HPLC, and analyzing and identifying to obtain the technetium-99m labeled triphenylphosphine derivative. The preparation method provided by the invention is simple, easy to operate, rich in raw materials and low in yield, is effectively used for preparing an SPECT myocardial perfusion imaging agent and is great in medical and commercial values.
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Paragraph 0026; 0027; 0028
(2018/09/21)
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- RAF-DEGRADING CONJUGATE COMPOUNDS
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The present disclosure provides, inter alia, RAF-Degrading Conjugate Compounds that are useful in the treatment of cancer and other RAF related diseases. Also provided are, pharmaceutical compositions, methods of treatment, and kits comprising a RAF- Degrading Conjugate Compound.
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Paragraph 0209; 0256
(2018/11/22)
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- Synthesis method of anesthetic bupivacaine impurities
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The invention relates to a synthesis method of anesthetic bupivacaine impurities. The synthesis method comprises the following steps: (a) adding 6-bromocaproic acid, dichloromethane and N,N-dimethylformamide to a reaction container, dropwise adding oxalyl chloride under the conditions of ice salt bath and nitrogen protection, performing reaction at 0-25 DEG C after addition, performing concentration after the reaction, adding toluene for concentration again to obtain a 6-bromohexanoyl chloride crude product, dissolving the 6-bromohexanoyl chloride crude product in dichloromethane, dropwise adding a dichloromethane solution of dimethylaniline under the conditions of ice salt bath and nitrogen protection, performing reaction at 5-10 DEG C after addition, and performing direct filtering, washing and drying after the reaction to obtain a compound ii; (b) adding the compound ii, n-butylamine, potassium carbonate and acetonitrile to another reaction container for reaction at 30-50 DEG C, andpurifying a product after reaction to obtain the anesthetic bupivacaine impurities. The anesthetic bupivacaine impurities prepared from 6-bromocaproic acid and oxalyl chloride as raw materials are set as drug quality standards by the European Pharmacopoeia, and the method has the advantages of simple process and convenient reaction steps.
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Paragraph 0007; 0008
(2018/11/22)
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- Discovery of a Small-Molecule Inhibitor of Interleukin 15: Pharmacophore-Based Virtual Screening and Hit Optimization
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Interleukin (IL)-15 is a pleiotropic cytokine, which is structurally close to IL-2 and shares with it the IL-2 β and γ receptor (R) subunits. By promoting the activation and proliferation of NK, NK-T, and CD8+ T cells, IL-15 plays important roles in innate and adaptative immunity. Moreover, the association of high levels of IL-15 expression with inflammatory and autoimmune diseases has led to the development of various antagonistic approaches targeting IL-15. This study is an original approach aimed at discovering small-molecule inhibitors impeding IL-15/IL-15R interaction. A pharmacophore and docking-based virtual screening of compound libraries led to the selection of 240 high-scoring compounds, 36 of which were found to bind IL-15, to inhibit the binding of IL-15 to the IL-2Rβ chain or the proliferation of IL-15-dependent cells or both. One of them was selected as a hit and optimized by a structure-activity relationship approach, leading to the first small-molecule IL-15 inhibitor with sub-micromolar activity.
- Quéméner, Agnès,Maillasson, Mike,Arzel, Laurence,Sicard, Benoit,Vomiandry, Romy,Mortier, Erwan,Dubreuil, Didier,Jacques, Yannick,Lebreton, Jacques,Mathé-Allainmat, Monique
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supporting information
p. 6249 - 6272
(2017/08/02)
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- (2S,4R)-Hyp-(S)-Phe-OMe dipeptide supported on imidazolium tagged molecules as recoverable organocatalysts for asymmetric aldol reactions using water as reaction medium
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Four novel chiral imidazolium tagged molecules derived from dipeptide (2S,4R)-Hyp-(S)-Phe-OMe were prepared and evaluated as organocatalysts in the asymmetric aldol reaction using water as solvent. It was found that catalysts incorporating the hexanoyl linker are active down to 5 mol% and afford aldol products with up to 94% yield, up to 98:2 dr and up to 97:3 er. This chiral imidazolium catalyst was reused up to 6 times without any loss in the stereoselectivity of asymmetric aldol reactions. By contrast, organocatalysts containing an acetyl linker proved to be highly unstable in protic solvents, and for that reason they could not be recovered and reused.
- Obregón-Zú?iga, Arturo,Juaristi, Eusebio
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p. 5373 - 5380
(2017/08/11)
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- Flexible analogues of WAY-267,464: Synthesis and pharmacology at the human oxytocin and vasopressin 1a receptors
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A previously identified, non-peptidic oxytocin (OT) receptor agonist WAY-267,464 (1) and nine novel derivatives (3, 4a-7a, 4b-7b) were synthesised and evaluated in vitro with the aim of systematically exploring hydrogen bonding interactions and ligand flexibility. All analogues were subjected to competition radioligand binding assays at human oxytocin (OT) and arginine vasopressin 1a (V1a) receptors. Physiological activity was determined using whole cell IP1 accumulation assays. Under these conditions, WAY-267,464 had higher affinity for the V1a receptor compared to the OT receptor (8.5x more selective) with poor functional selectivity (2x selective for OT receptor agonism over V1a receptor antagonism). Methylation of the resorcinol moiety (3) reversed the OT receptor pharmacological profile, removing agonist activity and inducing antagonist activity, without altering V1a receptor pharmacology. All flexible tethered derivatives removed OT receptor affinity and activity resulting in the generation of highly selective V1a receptor ligands.
- Jorgensen, William T.,Gulliver, Damien W.,Werry, Eryn L.,Reekie, Tristan,Connor, Mark,Kassiou, Michael
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p. 730 - 740
(2016/01/09)
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- Controlled generation of singlet oxygen by porphyrin-appended gold nanoparticles
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Porphyrin-appended gold nanoparticles with different chain lengths were synthesized to examine the control over photosensitization. The efficiencies evaluated by singletoxygen generation were adjusted by the average number of porphyrins on one gold nanoparticle and the particle size regardless of the linker chain length between porphyrin site and gold core.
- Shinohara, Akira,Shinmori, Hideyuki
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supporting information
p. 1341 - 1343
(2017/08/02)
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- NOVEL NICOTINE DNA VACCINES
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The present invention provides DNA-nanostructures comprising and at least one targeting moiety, wherein the at least one targeting moiety is linked to the DNA-nanostructure; and wherein the at least one targeting moiety is nicotine or a nicotine analogue. These compounds elicit an immunogenic response in individuals and are useful as vaccines for ameliorating nicotine dependence.
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Paragraph 0166
(2015/02/18)
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- Efficacious redox-responsive gene delivery in serum by ferrocenylated monomeric and dimeric cationic cholesterols
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Herein, we present the design and synthesis of new redox-active monomeric and dimeric (gemini) cationic lipids based on ferrocenylated cholesterol derivatives for gene delivery. The cationic cholesterols are shown to be transfection efficient after being formulated with the neutral helper lipid DOPE in the presence of serum (FBS). The redox activity of the resulting co-liposomes and their lipoplexes could be regulated using the alkanyl ferrocene moiety attached to the ammonium head groups of the cationic cholesterols. Atomic force microscopy (AFM), dynamic light scattering (DLS) and zeta potential measurements were performed to characterize the co-liposomal aggregates and their complexes with pDNA. The transfection efficiency of lipoplexes could be tuned by changing the oxidation state of the ferrocene moiety. The gene transfection capability was assayed in terms of green fluorescence protein (GFP) expression using pEGFP-C3 plasmid DNA in three cell lines of different origins, namely Caco-2, HEK293T and HeLa, in the presence of serum. The vesicles possessing ferrocene in the reduced state induced an efficient transfection, even better than a commercial reagent Lipofectamine 2000 (Lipo 2000) as evidenced by flow cytometry and fluorescence microscopy. All the co-liposomes containing the oxidized ferrocene displayed diminished levels of gene expression. Gene transfection events from the oxidized co-liposomes were further potentiated by introducing ascorbic acid (AA) as a reducing agent during lipoplex incubation with cells, leading to the resumption of transfection activity. Assessment of transfection capability of both reduced and oxidized co-liposomes was also undertaken following cellular internalization of labelled pDNA using confocal microscopy and flow cytometry. Overall, we demonstrate here controlled gene transfection activities using redox-driven, transfection efficient cationic monomeric and dimeric cholesterol lipids. Such systems could be used in gene delivery applications where transfection needs to be performed spatially or temporally. This journal is
- Vulugundam, Gururaja,Kumar, Krishan,Kondaiah, Paturu,Bhattacharya, Santanu
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supporting information
p. 4310 - 4320
(2015/04/14)
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- A Twist-Bend Nematic (NTB) Phase of Chiral Materials
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New chiral dimers consisting of a rod-like and cholesterol mesogenic units are reported to form a chiral twist-bend nematic phase (NTB) with heliconical structure. The compressibility of the NTB phase made of bent dimers was found to be as large as in smectic phases, which is consistent with the nanoperiodic structure of the NTB phase. The atomic force microscopy observations in chiral bent dimers revealed a periodicity of about 50 nm, which is significantly larger than the one reported previously for non-chiral compounds (ca. 10 nm).
- Gorecka, Ewa,Vaupoti, Nataa,Zep, Anna,Pociecha, Damian,Yoshioka, Jun,Yamamoto, Jun,Takezoe, Hideo
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supporting information
p. 10155 - 10159
(2015/09/01)
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- Co-liposomes of redox-active alkyl-ferrocene modified low MW branched PEI and DOPE for efficacious gene delivery in serum
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Herein, we present six new lipopolymers based on low molecular weight, branched polyethylenimine (BPEI 800 Da) which are hydrophobically modified using ferrocene terminated alkyl tails of variable lengths. The effects of degree of grafting, spacer length and the redox state of ferrocene in the lipopolymers on the self assembly properties were investigated in detail by TEM, AFM, DLS and zeta potential measurements. The assemblies displayed an oxidation induced increase in the size of the aggregates. The co-liposomes comprising the lipopolymer and a helper lipid, 1,2-dioleoyl phosphatidyl ethanolamine (DOPE), showed excellent gene (pDNA) delivery capability in a serum containing environment in two cancer cell lines (HeLa and U251 cells). Optimized formulations showed remarkably higher transfection activity than BPEI (25 kDa) and were also significantly better than a commercial transfection reagent, Lipofectamine 2000 as evidenced from both the luciferase activity and GFP expression analysis. Oxidation of ferrocene in the lipopolymers led to drastically reduced levels of gene transfection which was substantiated by reduced cellular internalization of fluorescently labelled pDNA as detected using confocal microscopy and flow cytometry. Moreover, the transfection inactive oxidized lipopolyplexes could be turned transfection active by exposure to ascorbic acid (AA) in cell culture medium during transfection. Endocytosis inhibition experiments showed that gene expression mediated by reduced formulations involved both clathrin and caveolae mediated pathways while the oxidized formulations were routed via the caveolae. Cytotoxicity assays revealed no obvious toxicity for the lipopolyplexes in the range of optimized transfection levels in both the cell lines studied. Overall, we have exploited the redox activity of ferrocene in branched PEI-based efficient polymeric gene carriers whose differential transfection activities could be harnessed for spatial or temporal cellular transfections.
- Kumar, Krishan,Vulugundam, Gururaja,Kondaiah, Paturu,Bhattacharya, Santanu
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p. 2318 - 2330
(2015/03/18)
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- Design, synthesis and biological evaluation of saccharin-based N-hydroxybenzamides as histone deacetylases (HDACs) inhibitors
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We report the development of a novel series of saccharin-based N-hydroxybenzamides as histone deacetylases inhibitors. Among them, 6j exhibited potent HDACs inhibitory activity against Hela nuclear extract. Further biological evaluation found 6i showed similar antiproliferative activities in vitro compared with the approved SAHA.
- Fu, Huansheng,Han, Leiqiang,Hou, Xuben,Dun, Yanyan,Wang, Lei,Gong, Xiaowei,Fang, Hao
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supporting information
p. 5774 - 5781
(2015/11/11)
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- Synthesis of quaternary, long-chain N-alkyl amides and their corrosion inhibition in acidic media
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New cationic surfactants were synthesized by the quaternization of a number of straight-chain amide derivatives with triethylamine or pyridine. The corrosion inhibition tests of the surface-active compounds were performed at room temperature for 24 h on carbon steel coupons in acidic media using the gravimetric method. The acidic media used were 1.5 M HCl and 1.5 M H 2SO4. Almost all of the synthesized cationic surfactants showed efficient inhibition of corrosion in the test. To establish the inhibition efficiencies of the inhibitors, surface characterization studies (contact angle measurements, SEM analysis and optical profilometer images) of the metal coupons used were performed.
- ?ztürk, Serkan,Y?ld?r?m, Ayhan,?etin, Mehmet,Tavasl?, Mustafa
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p. 471 - 481
(2014/05/20)
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- Optimization of troglitazone derivatives as potent anti-proliferative agents: Towards more active and less toxic compounds
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Δ2-Troglitazone derivatives were shown to exhibit anti-proliferative activity in a PPARγ-independent manner. We prepared various compounds in order to increase their potency and decrease their toxicity towards non-malignant primary cultured hepatocytes. Many compounds induced viabilities less than 20% at 10 μM on various cancer cell lines. Furthermore, five of them showed hepatocyte viability of 80% or more at 200 μM. In addition, compounds 17 and 18 exhibited promising maximum tolerated doses on a murine model, enabling future investigations.
- Bordessa, Andrea,Colin-Cassin, Christelle,Grillier-Vuissoz, Isabelle,Kuntz, Sandra,Mazerbourg, Sabine,Husson, Gauthier,Vo, Myriam,Flament, Stéphane,Martin, Hélène,Chapleur, Yves,Boisbrun, Michel
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p. 129 - 140
(2014/07/08)
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- THIAZOLIDINEDIONE DERIVATIVES, PREPARATION THEREOF AND USE THEREOF IN CANCER TREATMENT
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The present invention relates to thiazolidinedione derivatives, to the processes for preparing same and to the therapeutic use thereof for preventing or treating cancer, and more specifically breast cancer. These compounds are of formula (I) and exhibit, at a concentration of 100 μM, a hepatocyte viability preferably greater than 60%, preferably greater than 80% and more preferentially greater than 85%.
- -
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Paragraph 0137; 0138; 0143
(2015/01/06)
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- Synthesis and evaluation of novel ellipticines as potential anti-cancer agents
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Drugs that inhibit DNA topoisomerase I and DNA topoisomerase II have been widely used in cancer chemotherapy. We report herein the results of a focused medicinal chemistry effort around novel ellipticinium salts which target topoisomerase I and II enzymes with improved solubility. The salts were prepared by reaction of ellipticine with the required alkyl halide and evaluated for DNA intercalation, topoisomerase inhibition and growth inhibition against 12 cancer cell lines. Results from the topoisomerase I relaxation assay indicated that all novel ellipticine derivatives behaved as intercalating agents. At a concentration of 100 μM, specific topoisomerase I inhibition was not observed. Two of the derivatives under investigation were found to fully inhibit the DNA decatenation reaction at a concentration of 100 μM, indicative of topoisomerase II inhibition. N-Alkylation of ellipticine was found to enhance the observed growth inhibition across all cell lines and induce growth inhibition comparable to that of Irinotecan (CPT-11; GI50 1-18 μM) and in some cell lines better than Etoposide (VP-16; GI50 = 0.04-5.2 μM). 6-Methylellipticine was the most potent growth inhibitory compound assessed (GI50 = 0.47-0.9 μM). N-Alkylation of 6-methylellipticine was found to reduce this response with GI50 values in the range of 1.3-28 μM.
- Deane, Fiona M.,O'Sullivan, Elaine C.,Maguire, Anita R.,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam,McCarthy, Florence O.
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p. 1334 - 1344
(2013/05/21)
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- Catalytic asymmetric reductive acyl cross-coupling: Synthesis of enantioenriched acyclic α,α-disubstituted ketones
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The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a NiII/bis(oxazoline) catalyst in the presence of Mn0 as a stoichiometric reductant generates acyclic α,α-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.
- Cherney, Alan H.,Kadunce, Nathaniel T.,Reisman, Sarah E.
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supporting information
p. 7442 - 7445
(2013/06/27)
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- Synthesis of nitrogenated heterocycles by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)haloimines
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Highly optically enriched, protected, nitrogenated heterocycles with different ring sizes have been synthesized by a very efficient methodology consisting of the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl) haloimines followed by treatment with a base to promote an intramolecular nucleophilic substitution process. N-Protected aziridines, pyrrolidines, piperidines, and azepanes bearing aromatic, heteroaromatic, and aliphatic substituents have been obtained in very high yields and diastereomeric ratios up to >99:1. The free heterocycles can be easily obtained by a simple and mild desulfinylation procedure. Both enantiomers of the free heterocycles can be prepared with the same good results by changing the absolute configuration of the sulfur atom of the sulfinyl group.
- Pablo, Oscar,Guijarro, David,Yus, Miguel
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p. 9181 - 9189
(2013/10/08)
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- Quinazolino linked 4β-amidopodophyllotoxin conjugates regulate angiogenic pathway and control breast cancer cell proliferation
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A series of new conjugates of quinazolino linked 4β- amidopodophyllotoxins 10aa-af and 10ba-bf were synthesized and evaluated for their anticancer activity against human pancreatic carcinoma (Panc-1) as well as breast cancer cell lines such as MCF-7 and MDA-MB-231 by employing MTT assay. Among these conjugates, some of them like 10bc, 10bd, 10be and 10bf exhibited high potency of cytotoxicity. Flow cytometric analysis showed that these conjugates arrested the cell cycle in the G2/M phase and caused the increase in expression of p53 and cyclin B1 protein with concomitant decrease in Cdk1 thereby suggesting the inhibitory action of these conjugates on mitosis. Interestingly, we observed a decrease in expression of proteins that control the tumor micro environment such as VEGF-A, STAT-3, ERK1/2, ERK-p, AKT-1 ser 473 phosphorylation in compounds treated breast cancer cells. Further, these effective conjugates have exhibited inhibitory action on integrin (αVβIII). Furthermore, the MCF-7 cells that were arrested and lost the proliferative capacity undergo mitochondrial mediated apoptosis by activation of caspases-9. Thus these conjugates have the potential to control breast cancer cell growth by effecting tumor angiogenesis and invasion.
- Kamal, Ahmed,Tamboli, Jaki R.,Ramaiah, M. Janaki,Adil,Pushpavalli,Ganesh, Raksha,Sarma, Pranjal,Bhadra, Utpal,Pal-Bhadra, Manika
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p. 6414 - 6426
(2013/10/22)
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- Synthesis and anticancer activity of 4β-alkylamidochalcone and 4β-cinnamido linked podophyllotoxins as apoptotic inducing agents
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A series of 4β-alkylamidochalcone and 4β-cinnamido linked podophyllotoxin congeners have been synthesized. All the twenty nine compounds were evaluated for anticancer activity against five human cancer cell lines (A-549, A375, MCF-7, HT-29 and ACHN). Some of the synthesized compounds showed good anticancer activity that is comparable to etoposide. The IC50 of compounds 17a and 17f is 2.7 and 2.1 μM respectively against A-549 cancer cell line. Flow cytometric analysis showed that these two compounds arrested the cell cycle in the G2/M phase leading to caspase-3 dependent apoptotic cell death. Further, Hoechst 33258 staining and DNA fragmentation assay also suggested that 17a and 17f induced cell death by apoptosis.
- Kamal, Ahmed,Mallareddy, Adla,Suresh, Paidakula,Lakshma Nayak,Shetti, Rajesh V.C.R.N.C.,Sankara Rao,Tamboli, Jaki R.,Shaik, Thokhir B.,Vishnuvardhan,Ramakrishna
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experimental part
p. 530 - 545
(2012/02/14)
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- Liquid crystalline 4-(2,3 Dihydroxypropoxy) diphenyl 4-n-alcoxy acids
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4-(2,3 Dihydroxypropoxy) diphenyl 4-oxy-hexanoic acid and 4-(2,3 dihydroxypropoxy) diphenyl 4-oxy-undecanoic acid have been synthesized and analyzed by IR and NMR experiments. The liquid crystalline character and the phase transitions of these two acids have been studied by differential scanning calorimetry (DSC) and variable temperature X-ray diffraction (VTXRD). These two liquid crystalline monomers are designed to be flexible, rigid and polyfunctional, so that they can be used in the synthesis of new macromolecules with side chain liquid crystals.
- Lopez-Velazquez, Delia,Hernandez-Sosa, Armando R.,Perez, Ernesto,Castillo-Rojas, Susana
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experimental part
p. 175 - 184
(2012/04/05)
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- Consequences of linker length alteration of the α7 nicotinic acetylcholine receptor (nAChR) agonist, SEN12333
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A series of ligands based on SEN12333, containing either contracted or elongated alkyl chains, were synthesized and evaluated in molecular docking studies against a homology model of the α7 nicotinic acetylcholine receptor (nAChR) subtype. The predicted binding of all ligands was highly similar, with the exception of the analog containing a 5 methylene unit spacer. However, in vitro competition binding assays revealed that the ligands possessed dissimilar binding affinities, with a Ki range of more than an order of magnitude (Ki = 0.50 to >10 μM), and only SEN12333 itself exhibited functional activity at the α7 nAChR.
- Beinat, Corinne,Banister, Samuel D.,Van Prehn, Saundra,Doddareddy, Munikumar Reddy,Hibbs, David,Sako, Michael,Chebib, Mary,Tran, Thao,Al-Muhtasib, Nour,Xiao, Yingxian,Kassiou, Michael
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supporting information; experimental part
p. 2380 - 2384
(2012/05/05)
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- Rate constants for cyclizations of α-hydroxy radical clocks
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The 1-hydroxy-1-methyl-6,6-diphenyl-5-hexenyl radical (4a) and the 1-hydroxy-1-methyl-7,7-diphenyl-6-heptenyl radical (4b) were prepared from the corresponding PTOC esters (anhydrides of a carboxylic acid and N-hydroxypyridine-2-thione). The key step in the synthetic method for the precursors was a coupling reaction of the respective carboxylic acids with the thiohydroxamic acid, which was conducted for ca. 5 min and followed rapidly by chromatography. Rate constants for cyclizations of radicals 4a and 4b in acetonitrile and in THF were measured directly between -30 and 60 °C by laser flash photolysis methods. The Arrhenius functions in acetonitrile are log k = 9.9-2.6/2.303RT and log k = 8.9-4.4/2.303RT (kcal mol-1) for 4a and 4b, respectively. Rate constants for cyclizations at room temperature of 9 × 107 s-1 and 4 × 105 s -1 are somewhat larger than the rate constants for cyclizations of analogous alkyl radicals. Crude rate constants at room temperature for H-atom trapping of 4a by thiophenol and 4b by t-butylthiol were kT = 1.2 × 109 M-1 s-1 and kT = 2 × 107 M-1 s-1, respectively, which are modestly larger than rate constants for reactions of alkyl radicals with the same trapping agents.
- DeZutter, Christopher B.,Horner, John H.,Newcomb, Martin
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body text
p. 516 - 522
(2011/03/16)
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- N-alkylated cyclen cobalt(III) complexes of 1-(chloromethyl)-3-(5,6,7- trimethoxyindol-2-ylcarbonyl)-2,3-dihydro-1H-pyrrolo[3,2-f]quinolin-5-ol DNA alkylating agent as hypoxia-activated prodrugs
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A series of cobalt complexes of the potent DNA minor groove alkylator 1-(chloromethyl)-3-(5,6,7-trimethoxyindol-2-ylcarbonyl)-2,3-dihydro-1H- pyrrolo[3,2-f]quinolin-5-ol (seco-6-azaCBI-TMI) were prepared from a series of N-substituted cyclen ligands. The final N-substituted complexes carried formal overall charges ranging from +2 to -2 and showed limited improvements in solubility. They showed similar stabilities to that of the complex with the unsubstituted cyclen ligand, and large but variable attenuation of the cytotoxicity of the free alkylator (2-30-fold), compared to 150-fold for the unsubstituted ligand. However, they had oxic/hypoxic ratios (2-22-fold) comparable to that of the unsubstituted cyclen complex (5).
- Lu, Guo-Liang,Stevenson, Ralph J.,Chang, John Yu-Chih,Brothers, Penelope J.,Ware, David C.,Wilson, William R.,Denny, William A.,Tercel, Moana
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experimental part
p. 4861 - 4867
(2011/09/21)
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- Reversible redox of NADH and NAD+ at a hybrid lipid bilayer membrane using ubiquinone
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Here, we report the reversible interconversion between NADH and NAD + at a low overpotential, which is in part mediated by ubiquinone embedded in a biomimetic membrane to mimic the initial stages of respiration. This system can be used as a platform to examine biologically relevant electroactive molecules embedded in a natural membrane environment and provide new insights into the mechanism of biological redox cycling.
- Ma, Wei,Li, Da-Wei,Sutherland, Todd C.,Li, Yang,Long, Yi-Tao,Chen, Hong-Yuan
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supporting information; experimental part
p. 12366 - 12369
(2011/10/02)
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- ANTIMICROBIAL SURFACES
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The present invention relates to compositions having a light activated antimicrobial material connected to an environmental surface, such as fabric, through a linking moiety and a mediator polymer. Also taught herein are surfaces to which the compositions of this invention are attached to impart antimicrobial activity to those surfaces. The present invention facilitates or makes possible the attachment of certain light activated antimicrobial material such as Rose Bengal dye to a surface to achieve antimicrobial activity.
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Page/Page column 5
(2010/03/02)
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- Fluoroalkene modification of mercaptoacetamide-based histone deacetylase inhibitors
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Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. The mercaptoacetoamide-based inhibitors are reported to be less toxic than hydroxamate and are worthy of further consideration. Therefore, we have designed a series of analogs as potential inhibitors of HDACs, in which the mercaptoacetamide group was replaced by (mercaptomethyl)fluoroalkene, and their HDAC inhibitory activity was evaluated. Subnanomolar inhibition was observed for all synthetic compounds.
- Osada, Satoshi,Sano, Satoshi,Ueyama, Mariko,Chuman, Yoshiro,Kodama, Hiroaki,Sakaguchi, Kazuyasu
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scheme or table
p. 605 - 611
(2010/05/02)
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- Synthesis and Cav2.2 binding data for non-peptide mimetics of ω-conotoxin GVIA based on a 5-amino-anthranilamide core
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A simple and efficient method has been developed for the synthesis of two anthranilamide-based non-peptide mimetics of ?-conotoxin GVIA. These anthranilamide derivatives aim to mimic the K2, R17, and Y13 residues of the peptide. The synthetic route described enables the rapid synthesis of anthranilamide analogues with identical alkyl chain lengths. The target compounds show affinity to rat N-type voltage gated calcium channels (Ca v2.2) with EC50 values of 42 and 75 ?M. CSIRO 2008.
- Duggan, Peter J.,Faber, Jonathan M.,Graham, Janease E.,Lewis, Richard J.,Lumsden, Natalie G.,Tuck, Kellie L.
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- Identification of terfenadine as an inhibitor of human CD81-receptor HCV-E2 interaction: Synthesis and structure optimization
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Terfenadine (4-[4-(hydroxydiphenylmethyl)-1-piperidyl]-1-(4-tert- butylphenyl)-butan-1-ol) was identified in a biological screening to be a moderate inhibitor (27 % inhibition) of the CD81-LEL-HCV-E2 interaction. To increase the observed biological activity, 63 terfenadine derivates were synthesized via microwave assisted nucleophilic substitution. The prepared compounds were tested for their inhibitory potency by means of a fluorescence labeled antibody assay using HUH7.5 cells. Distinct structure-activity relationships could be derived. Optimization was successful, leading to 3g, identfied as the most potent compound (69 % inhibition). Experiments with viral particles revealed that there might be additional HCV infection reducing mechanisms.
- Holzer, Marcel,Ziegler, Sigrid,Albrecht, Beatrice,Kronenberger, Bernd,Kaul, Artur,Bartenschlager, Ralf,Kattner, Lars,Klein, Christian D.,Hartmann, Rolf W.
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p. 1081 - 1110
(2008/09/21)
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- Searching for new NO-donor aspirin-like molecules: A new class of nitrooxy-acyl derivatives of salicylic acid
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A new class of products in which the phenol group of salicylic acid is linked to alkanoyl moieties bearing nitrooxy functions has been synthesized and studied for their polyvalent actions. The products were stable in acid and neutral media, while they were hydrolyzed in human serum. Their half-lives were dependent upon the structure of alkanoyl moieties. The products showed anti-inflammatory activities similar to aspirin when tested in the carrageenan-induced paw edema assay in the rat. Interestingly, unlike aspirin, they showed reduced or no gastrotoxicity in a lesion model in rats at equimolar doses. A number of them were able to inhibit platelet aggregation induced by collagen in human platelet-rich plasma. All of the products were capable of relaxing rat aortic strips precontracted with phenylephrine in a concentration-dependent manner. Selected members of this new class of nonsteroidal anti-inflammatory drugs might represent possible safer alternatives to aspirin in different clinical settings.
- Lazzarato, Loretta,Donnola, Monica,Rolando, Barbara,Marini, Elisabetta,Cena, Clara,Coruzzi, Gabriella,Guaita, Elena,Morini, Giuseppina,Fruttero, Roberta,Gasco, Alberto,Biondi, Stefano,Ongini, Ennio
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p. 1894 - 1903
(2008/12/20)
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- A novel series of potent and selective ketone histone deacetylase inhibitors with antitumor activity in vivo
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Histone deacetylase (HDAC) inhibitors offer a promising strategy for cancer therapy, and the first generation HDAC inhibitors are currently in the clinic. Entirely novel ketone HDAC inhibitors have been developed from the cyclic tetrapeptide apicidin. These compounds show class I subtype selectivity and levels of cellular activity comparable to clinical candidates. A representative example has demonstrated tumor growth inhibition in a human colon HCT-116 carcinoma xenograft model comparable to known inhibitors.
- Jones, Philip,Altamura, Sergio,De Francesco, Raffaele,Paz, Odalys Gonzalez,Kinzel, Olaf,Mesiti, Giuseppe,Monteagudo, Edith,Pescatore, Giovanna,Rowley, Michael,Verdirame, Maria,Steinkühler, Christian
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p. 2350 - 2353
(2008/12/22)
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- A new one-pot synthetic method for selenium-containing medium-sized α,β-unsaturated cyclic ketones
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The reaction of tetrahydroselenopyran-2-one (7) with ethynyllithiums 20a-h, followed by treatment with aqueous 5% H2SO4 successfully led to a two-carbon ring expansion to give the 2-substituted 5,6,7,8-tetrahydroselenocin-4-ones 21a-h in 43-95% yields. Seven- to nine-membered γ-selena-α,β-unsaturated cyclic ketones 22-26 and a 5,6,7,8-tetrahydrotellurocin-4-one 27 were also prepared from the corresponding selenolactones or tellurolactone in a one-pot reaction.
- Sashida, Haruki,Nakayama, Akemi,Kaname, Mamoru
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experimental part
p. 3229 - 3236
(2009/05/07)
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