- Kinetics and mechanistic investigation of epoxy-anhydride compositions cured with quaternary phosphonium salts as accelerators
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Mechanism and curing kinetics of bisphenol A epoxy resin-iso-methyltetrahydrophthalic anhydride compositions using quaternary phosphonium salts as accelerators were investigated by differential scanning calorimetry (DSC) and electrospray mass-spectrometry (ESI-MS). The DSC method was applied to investigate curing kinetics and apparent activation energy values for the overall curing process. The DSC results showed that some of the phosphonium salts lead to a lower activation energy, that means they are more effective accelerators for the curing of epoxy-anhydride systems. The mechanism of curing was studied by ESI-MS using the model reaction of epichlorohydrin (E) with phthalic anhydride (PA) in the presence of phosphonium salts or 2-methylimidazole. Products containing the alkyl moiety of the phosphonium salt in form of alkyl esters could be identified. This suggests that the phosphonium salts activate the anhydride by electrophilic attack.
- Amirova, Lyaysan R.,Burilov, Alexander R.,Amirova, Liliya M.,Bauer, Ingmar,Habicher, Wolf D.
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- Cis alkenes stabilized by intramolecular sulphur?π interactions
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A series of alkenes with bistable isomers were obtained containing a thiophene/azoheteroaryl backbone. Visible light and heat-induced reversible cis ? trans isomerizations were evidenced by UV-Vis and 1H NMR spectra. The stabilization of cis alkenes was attributed to intramolecular sulphur?π (S?π) interactions, which were further supported by theoretical calculations.
- Zhao, Xiaolei,Zheng, Wei,Zhang, Yi,Huang, Wei
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- Investigating Variation of the Pnicogen Nucleophilic Heteroatom on Ionic Liquid Solvent Effects in Bimolecular Nucleophilic Substitution Processes
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A series of nucleophiles containing Group 15 nucleophilic heteroatoms has been used to expand and develop the current understanding of ionic liquid solvent effects on bimolecular nucleophilic substitution processes. It was found that when using arsenic-, antimony- and bismuth-based nucleophiles, rate constant enhancement was observed for all solvent compositions containing ionic liquids. This rate constant enhancement was driven by ionic liquid/transition state interactions, which contrasts with previous studies on earlier Group 15 nucleophiles. This study provides a holistic understanding and augments the predictive framework for the effects of ionic liquids on bimolecular nucleophilic substitution processes, with the potential for these periodic trends to be broadly applied.
- Schaffarczyk McHale, Karin S.,Haines, Ronald S.,Harper, Jason B.
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- Synthesis and crystal structures of (Benzyl)triphenylphosphonium Bromides, [C6H5-CH2P(C6H5) 3]+Br- and [C6H5-CH2P(C6H5) 3]+Br3-
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(Benzyl)triphenylphosphonium bromide, [C6H5-CH2P(C6H5) 3]+Br- (CH2Cl2) (1) has been prepared by the reaction of triphenylphosphine with benzylbromide and its structure determined. The colorless crystals are triclinic, space group P1, Z = 2, a = 976.0(3), b = 1069.0(3), c = 1226.1(4) pm. α = 94.13(3), β = 104.70(3), γ = 100.14(3)°. The lattice contains Br- anions and [C6H5-CH2P(C6H5) 3]+ cations. [C6H5-CH2P(C6H5) 33]Br3 (2) has been obtained by treating compound 1 with equimolar quantities of elemental bromine in methylene chloride solution. The red crystals of 2 are monoclinic, space group P21/c, Z = 4, a = 917.9(2), b = 1022.6(2), c = 2573.6(5) pm, β = 99.11(2)°, and comprise[C6H5-CH2P(C6H 5)3]+ cations and linear, slightly asymmetrical Br3- anions with bromine-bromine distances of 246.19(11) and 263.69(11) pm.
- Hübner,Wulff-Molder,Vogt,Meisel
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- Functionalized Cyclopropanes as Versatile Intermediates for the Diversity-Oriented Synthesis of γ-Lactones, γ-Lactams and δ-Lactams
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A two-step procedure for the preparation of cyclopropanecarboxaldehyde-1,1-diester from a γ,δ-epoxyester and its synthetic versatility are described herein. The epoxide ring-opening/cyclopropanation process occurs in the presence of Mg(ClO 4) 2under heating, resulting in cyclopropanemethanol-1,1-diester in 65% yield. A mild TEMPO-mediated oxidation of this substrate readily generated the corresponding aldehyde in 75% yield, which was applied in the one-pot synthesis of four cyclopropylidene-γ-lactams and three δ-lactams. In addition, vinylcyclopropanes were obtained through the Wittig reaction of the aldehyde with phosphonium salts and used as precursors for tetrahydrofurans.
- Maximiano, Adrielle P.,Ramos, Giovana S.,Marques, Marcelo V.,Sá, Marcus M.
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- Photochemical Synthesis and Electronic Properties of Extended Corannulenes with Variable Fluorination Pattern
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The first family of extended and fluorinated corannulenes is prepared through a highly efficient and modular synthetic strategy. In this strategy, corannulene aldehyde could be combined with the fluorine-carrying phosphonium ylides to furnish stilbene-like vinylene precursors. A photochemically induced oxidative cyclization process of these precursors gives rise to the fluorinated and curved polycyclic aromatic hydrocarbons. A UV-vis absorption study shows that aromatic extension results in a bathochromic shift of about 12 nm. Fluorination further shifts the absorption spectrum to the red region, and a maximum shift of about 22 nm is detected for a compound carrying two trifluoromethyl groups. A cyclic and square-wave voltammetry investigation reveals that the extension of the corannulene scaffold increases the reduction potential by 0.11 V. Placement of fluorine or trifluoromethyl groups further enhances the electron affinities. In this regard, the presence of one trifluoromethyl group equals the effect of three aromatic fluorine atoms. Molecules with two trifluoromethyl groups, meanwhile, exhibit the highest reduction potentials of -1.93 and -1.83 V. These values are 0.37 and 0.46 V higher than those of the parental corannulene and demonstrate the utility of the present design concept by efficiently accessing effective electron acceptors based on the buckybowl motif.
- Halilovic, Dzeneta,Budanovi?, Maja,Wong, Zeng R.,Webster, Richard D.,Huh, June,Stuparu, Mihaiela C.
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- Catalyst-free room-temperature iClick reaction of molybdenum(II) and tungsten(II) azide complexes with electron-poor alkynes: Structural preferences and kinetic studies
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Two isostructural and isoelectronic group VI azide complexes of the general formula [M(η3-allyl)(N3)(bpy)(CO)2] with M = Mo, W and bpy = 2,2′-bipyridine were prepared and fully characterized, including X-ray structure analysis. Both reacted smoothly with electron-poor alkynes such as dimethyl acetylenedicarboxylate (DMAD) and 4,4,4-trifluoro-2-butynoic acid ethyl ester in a catalyst-free room-temperature iClick [3 + 2] cycloaddition reaction. Reaction with phenyl(trifluoromethyl)acetylene, on the other hand, did not lead to any product formation. X-ray structures of the four triazolate complexes isolated showed the monodentate ligand to be N2-coordinated in all cases, which requires a 1,2-shift of the nitrogen from the terminal azide to the triazolate cycloaddition product. On the other hand, a 19F NMR spectroscopic study of the reaction of the fluorinated alkyne with the tungsten azide complex at 27 °C allowed detection of the N1-coordinated intermediate. With this method, the second-order rate constant was determined as (7.3 ± 0.1) × 10-2 M-1 s-1, which compares favorably with that of first-generation compounds such as difluorocyclooctyne (DIFO) used in the strain-promoted azide-alkyne cycloaddition (SPAAC). In contrast, the reaction of the molybdenum analogue was too fast to be studied with NMR methods. Alternatively, solution IR studies revealed pseudo-first order rate constants of 0.4 to 6.5 × 10-3 s-1, which increased in the order of Mo > W and F3C-CC-COOEt > DMAD.
- Schmid, Paul,Maier, Matthias,Pfeiffer, Hendrik,Belz, Anja,Henry, Lucas,Friedrich, Alexandra,Sch?nfeld, Fabian,Edkins, Katharina,Schatzschneider, Ulrich
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- Supramolecular Recognition of Quaternary Phosphonium Cations
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The modes of supramolecular recognition of quaternary phosphonium cations mediated by 1,1′-bi-2-naphthol (BINOL) are identified and characterized. In contrast to our previous work on ammonium cations, the recognition of the quaternary phosphonium cations via the formation of a PR4+·Br–·BINOL ternary complex was found to be mediated by a hydrogen bond from an α-carbon center of the phosphonium cation, encapsulation within a continuous hydrogen bond network between the halide–BINOL network, or a combination of these effects working in tandem. The solid state structures of these ternary complexes were analyzed by X-ray crystallography, aided by Hirshfeld surface analysis, to confirm the presence of characteristic intermolecular interactions for the identified modes. In all cases, the quaternary phosphonium cation acts as a hydrogen bond donor (HBD) in these supramolecular interactions, and thus this is the key to the recognition process with BINOL. The characterization of such mechanisms offers insight into the supramolecular and crystal engineering communities in the future design of agents capable of the supramolecular recognition of phosphonium cations and their abstraction from the solution phase.
- Walsh, Mark P.,Kitching, Matthew O.
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- Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates
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Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.
- Ahmed Fouad, Manar,Ferretti, Francesco,Formenti, Dario,Milani, Fabio,Ragaini, Fabio
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supporting information
p. 4876 - 4894
(2021/09/20)
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- One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols
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Two approaches for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs have been developed. The developed protocols are complementary: the direct mixing of alcohol, trimethylsilyl bromide, and triphenylphosphine in 1,4-dioxane followed by heating at 80 °C was found to be more efficient for acid-sensitive substrates, such as salicyl or furfuryl alcohols as well as secondary benzyl alcohols, while a one-pot procedure including sequential addition of trimethylsilyl bromide and triphenylphosphine gave higher yields for benzyl alcohols bearing electroneutral or electron-withdrawing substituents.
- Abaev, Vladimir T.,Chalikidi, Petrakis N.,Demidov, Oleg P.,Gutnov, Andrey V.,Magkoev, Taimuraz T.,Trushkov, Igor V.,Uchuskin, Maxim G.
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p. 9838 - 9846
(2021/07/28)
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- Reactions of benzyltriphenylphosphonium salts under photoredox catalysis
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The development of benzyltriphenylphosphonium salts as alkyl radical precursors using photoredox catalysis is described. Depending on substituents, the benzylic radicals may couple to form C-C bonds or abstract a hydrogen atom to form C-H bonds. A natural product, brittonin A, was also synthesized using this method.
- Boldt, Andrew M.,Dickinson, Sidney I.,Ramirez, Jonathan R.,Benz-Weeden, Anna M.,Wilson, David S.,Stevenson, Susan M.
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supporting information
p. 7810 - 7815
(2021/09/28)
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- Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters
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A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.
- Frydrych, Ivo,Urban, Milan,?arek, Jan,Benická, Sandra,D?ubák, Petr,Gurská, Soňa,Hajdúch, Marián,Kotulová, Jana,Li?ková, Barbora,Olejníková, Denisa,Pokorny, Jan
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- Understanding the regioselectivity in the oxidative condensation of catechins using pyrogallol-type model compounds
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Catechins are found in many foods, including tea. These compounds are bioactive. Previous studies have shown that catechins form dimers on oxidation, and there seem to be distinct regioselective effects. However, the dimerization mechanism and regioselectivity are not well understood. Therefore, we investigated the oxidation of four pyrogallol-type model compounds of epigallocatechin (EGC) having various substituents with 1 equiv of copper chloride and 30% dioxane in water. Compounds having 2C-2C or 2C-4C bonds in the B-ring were obtained in different product ratios. Comparison of the oxidation rates of each compound revealed that the model compounds having an oxygen atom corresponding to the 1-position of the C-ring of EGC underwent slow oxidation. In addition, using density functional theory calculations, we found that the highest occupied molecular orbital energies of these compounds were higher than those of the others. Further, the 2C-2C-bonded oxidation product having an A-ring and an oxygen atom at the C-ring 1-position was confirmed to have the highest thermodynamic stability. From these results, it is suggested that the regioselective condensation reaction of the catechin B-ring is related to interactions between the A-rings, as indicated by earlier studies, and the presence of oxygen at the 1-position of the C-ring in EGC.
- Yanase, Emiko,Ochiai, Yuto,Hirose, Sayumi
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supporting information
p. 12359 - 12366
(2020/11/10)
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- Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes
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In this paper, we revealed a metal-free and visible light photoinduced method for the rapid construction of spirobi[indene] skeletons, providing a simple and efficient way for easy access to spirobi[indene] scaffolds under mild conditions along with a broad substrate scope and good functional group tolerance.
- Li, Quanzhe,Liu, Jiaxin,Shi, Min,Wei, Yin
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supporting information
(2020/03/26)
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- Phenalenannulations: Three-Point Double Annulation Reactions that Convert Benzenes into Pyrenes
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3-Point annulations, or phenalenannulations, transform a benzene ring directly into a substituted pyrene by “wrapping” two new cycles around the perimeter of the central ring at three consecutive carbon atoms. This efficient, modular, and general method for π-extension opens access to non-symmetric pyrenes and their expanded analogues. Potentially, this approach can convert any aromatic ring bearing a -CH2Br or a -CHO group into a pyrene moiety. Depending upon the workup choices, the process can be directed towards either tin- or iodo-substituted product formation, giving complementary choices for further various cross-coupling reactions. The two-directional bis-double annulation adds two new polyaromatic extensions with a total of six new aromatic rings at a central core.
- Alabugin, Igor V.,Dos Santos, Nikolas R.,Hanson, Kenneth,Hu, Chaowei,Kawade, Rahul Kisan,Lin, Xinsong,Watson, Noelle
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supporting information
p. 14352 - 14357
(2020/07/20)
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- Rhodium catalyzed C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates and analogs
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The C-C bond cleavage/coupling of 2-(azetidin-3-ylidene)acetates with aryl boronic acids catalyzed by a rhodium complex was studied with a "conjugate addition/β-C cleavage/protonation" strategy.
- Yang, Xuan,Kong, Wei-Yu,Gao, Jia-Ni,Cheng, Li,Li, Nan-Nan,Li, Meng,Li, Hui-Ting,Fan, Jun,Gao, Jin-Ming,Ouyang, Qin,Xie, Jian-Bo
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supporting information
p. 12707 - 12710
(2019/10/28)
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- Anti-oligomerization sheet molecules: Design, synthesis and evaluation of inhibitory activities against α-synuclein aggregation
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Aggregation of α-synuclein (α-Syn) play a key role in the development of Parkinson Disease (PD). One of the effective approaches is to stabilize the native, monomeric protein with suitable molecule ligands. We have designed and synthesized a series of sheet-like conjugated compounds which possess different skeletons and various heteroatoms in the two blocks located at both ends of linker, which have good π-electron delocalization and high ability of hydrogen-bond formation. They have shown anti-aggregation activities in vitro towards α-Syn with IC50 down to 1.09 μM. The molecule is found binding in parallel to the NACore within NAC domain of α-Syn, interfering aggregation of NAC region within different α-Syn monomer, and further inhibiting or slowing down the formation of α-Syn oligomer nuclei at lag phase. The potential inhibitor obtained by our strategy is considered to be highly efficient to inhibit α-Syn aggregation.
- Liu, Hao,Chen, Li,Zhou, Fei,Zhang, Yun-Xiao,Xu, Ji,Xu, Meng,Bai, Su-Ping
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supporting information
p. 3089 - 3096
(2019/06/14)
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- Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C?H Insertion of Donor/Donor Carbenes
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We employ a single catalyst/oxidant system to enable the asymmetric syntheses of indolines, benzodihydrothiophenes, and indanes by C?H insertion of donor/donor carbenes. This methodology enables the rapid construction of densely substituted five-membered rings that form the core of many drug targets and natural products. Furthermore, oxidation of hydrazones to the corresponding diazo compounds proceeds in situ, enabling a relatively facile one- or two-pot protocol in which isolation of potentially explosive diazo alkanes is avoided. Regioselectivity studies were performed to determine the impact of sterics and electronics in donor/donor metal carbene C?H insertions to form indolines. This methodology was applied to a variety of substrates in high yield, diastereomeric, and enantiomeric ratios and to the synthesis of a patented indane estrogen receptor agonist with anti-cancer activity.
- Souza, Lucas W.,Squitieri, Richard A.,Dimirjian, Christine A.,Hodur, Blanka M.,Nickerson, Leslie A.,Penrod, Corinne N.,Cordova, Jesus,Fettinger, James C.,Shaw, Jared T.
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supporting information
p. 15213 - 15216
(2018/10/31)
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- Structural development of tetrachlorophthalimides as liver X receptor β (LXRβ)-selective agonists with improved aqueous solubility
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LXRβ-selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. We have reported a series of tetrachlorophthalimide analogs as an LXRβ-selective agonist. However, they exhibited poor aqueous solubility probably due to its high hydrophobicity and highly rigid and plane structure. In this report, we present further structural development of tetrachloro(styrylphenyl)phthalimides as the LXRβ-selective agonists with improved aqueous solubility.
- Nomura, Sayaka,Endo-Umeda, Kaori,Fujii, Shinya,Makishima, Makoto,Hashimoto, Yuichi,Ishikawa, Minoru
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p. 796 - 801
(2018/02/09)
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- Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds
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A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to access various functionalized thiophenes. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes. Mechanistically, DMSO plays a role of oxidant and S3?- in situ generated from K2S is involved.
- Chen, Liang,Min, Hao,Zeng, Weilan,Zhu, Xiaoming,Liang, Yun,Deng, Guobo,Yang, Yuan
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supporting information
p. 7392 - 7395
(2019/01/03)
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- Ionic Liquids as Solvents for SN2 Processes. Demonstration of the Complex Interplay of Interactions Resulting in the Observed Solvent Effects
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Bimolecular nucleophilic substitution reactions between triphenylphosphine and benzylic electrophiles have been examined in an ionic liquid to probe interactions with species along the reaction coordinate. Trends in the rate constant were found on both varying the leaving group and the electronic nature of the aromatic ring. In all the cases considered, interactions between the components of the ionic liquid and the transition state were shown to be more significant in determining reaction outcome than previously observed for this class of reaction. This demonstrates the importance of considering interactions of the ionic liquid components with all species along the reaction coordinate when investigating the origin of ionic liquid solvent effects, along with how such effects might be exploited.
- Schaffarczyk McHale, Karin S.,Haines, Ronald S.,Harper, Jason B.
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p. 1162 - 1168
(2019/01/04)
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- One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed C=H Functionalization
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A dehydrogenative oxygenation of C(sp2)=H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho-alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.
- Yang, Dejun,Zhu, Yifei,Yang, Na,Jiang, Qiangqiang,Liu, Renhua
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p. 1731 - 1735
(2016/06/09)
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- DOPAMINE D3 RECEPTOR ANTAGONISTS COMPOUNDS
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The disclosure is directed to novel dopamine D3 receptor antagonists, processes for their preparation, intermediates used in these processes, pharmaceutical compositions containing them and their use in therapy, including treating drug dependency and psychosis.
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Page/Page column 314
(2016/05/19)
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- Development of Tetrachlorophthalimides as Liver X Receptor β (LXRβ)-Selective Agonists
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Liver X receptor (LXR) agonists are candidates for the treatment of atherosclerosis via induction of ABCA1 (ATP-binding cassette A1) gene expression, which contributes to reverse cholesterol transport (RCT) and to cholesterol efflux from the liver and intestine. However, LXR agonists also induce genes involved in lipogenesis, such as SREBP-1c (sterol regulatory binding element protein 1c) and FAS (fatty acid synthase), thereby causing an undesirable increase in plasma and hepatic triglyceride (TG) levels. Recent studies indicate that LXRα contributes to lipogenesis in liver, and selective LXRβ activation improves RCT in mice. Therefore, LXRβ-selective agonists are promising candidates to improve atherosclerosis without increasing plasma or hepatic TG levels. However, the ligand-binding domains in the two LXR isoforms α/β share high sequence identity, and few LXR ligands show subtype selectivity. In this study we identified a tetrachlorophthalimide analogue as an LXRβ-selective agonist. Structural development led to (E)-4,5,6,7-tetrachloro-2-(2-styrylphenyl)isoindoline-1,3-dione (24 a), which shows potent and selective LXRβ agonistic activity in reporter gene assays. In binding assays, compound 24 a bound to LXRβ preferentially over LXRα. It also induced the expression of ABCA1 mRNA but not SREBP-1c mRNA in cells. Compound 24 a appears to be a promising lead compound for therapeutic agents to treat atherosclerosis without the side effects induced by LXRα/β dual agonists.
- Nomura, Sayaka,Endo-Umeda, Kaori,Makishima, Makoto,Hashimoto, Yuichi,Ishikawa, Minoru
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p. 2347 - 2360
(2016/10/25)
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- DOPAMINE D2 RECEPTOR LIGANDS
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The present invention relates to novel dopamine D2 receptor ligands. The invention further relates to functionally-biased dopamine D2 receptor ligands and the use of these compounds for treating or preventing central nervous system and systemic disorders associated with dysregulation of dopaminergic activity. The present invention relates to novel compounds that modulate dopamine D2 receptors. In particular, compounds of the present invention show functional selectivity at the dopamine D2 receptors and exhibit selectivity downstream of the D2 receptors, on the 0- arrestin pathway and/or on the cAMP pathway.
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Page/Page column 228
(2016/07/05)
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- Design, synthesis and SAR study of novel sulfonylureas containing an alkenyl moiety
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A series of sulfonylurea compounds was designed and synthesized via introducing an alkenyl moiety into the aryl-5 position and most title compounds exhibited enhanced antifungal activities and limited herbicidal activities compared with chlorsulfuron. Then, a CoMSIA calculation for antifungal activities was carried out to establish a 3D-QSAR model in which a cross-validated q2 of 0.585 and a correlation coefficient r2 of 0.989 were obtained. The derived model revealed that hydrophobic and electrostatic fields were the two most important factors for antifungal activity. Structure optimization was performed according to the CoMSIA model and compound 9z was found to be as potent as chlorothalonil in vitro against C. cornigerum, the pathogen of the wheat sharp eyespot disease. In order to study the fungicidal mechanism, 9z was successfully docked into yeast AHAS using a flexible molecular docking method and the resulting binding pattern was similar to that of chlorimuron-ethyl, indicating that the antifungal activity of compounds 9 was probably due to the inhibition of fungal AHAS.
- Wei, Wei,Cheng, Dandan,Liu, Jingbo,Li, Yuxin,Ma, Yi,Li, Yonghong,Yu, Shujing,Zhang, Xiao,Li, Zhengming
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p. 8356 - 8366
(2016/09/09)
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- Nitrogen: Versus phosphorus nucleophiles-how changing the nucleophilic heteroatom affects ionic liquid solvent effects in bimolecular nucleophilic substitution processes
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A series of nitrogen and phosphorus nucleophiles have been investigated to determine whether the previously established ionic liquid solvent effects on a bimolecular nucleophilic substitution (SN2) reaction vary with the nature of the nucleophilic centre. Reaction of group 15 triphenyl nucleophiles with benzyl bromide showed a different trend in the rate constant with increasing proportions of ionic liquid in the reaction mixture than was observed with pyridine. This result suggests additional interactions are important; a supposition supported by differences in reaction outcome observed when the electrophile was varied in reactions with triphenylphosphine. A novel ionic liquid solvent effect was observed in the reaction of tributylamine with benzyl bromide, with the position of equilibrium varying with the proportions of the ionic liquid present in the reaction mixture. Overall, the work presented demonstrates the importance of considering all possible interactions between an ionic liquid solvent and species along the reaction coordinate and has expanded upon our current predictive framework for ionic liquid solvent effects. Such understanding is important as it allows further development of a predictive framework for the application of ionic liquids in preparative chemistry.
- Schaffarczyk McHale, Karin S.,Hawker, Rebecca R.,Harper, Jason B.
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supporting information
p. 7437 - 7444
(2016/09/12)
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- Ferrocene derivative containing carbon-carbon and carbon-nitrogen double-bond long-chain conjugated system and preparation method and application of ferrocene derivative
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The invention discloses a ferrocene derivative containing a carbon-carbon and carbon-nitrogen double-bond long-chain conjugated system and a preparation method and application of the ferrocene derivative. The structural formula of the ferrocene derivative is as shown in the specification. The ferrocene derivative is good in second-order and third-order non-linear optical activity, and can be used as a photoelectric material.
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Paragraph 0103
(2016/10/09)
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- Synthesis and anti-inflammatory activity of phenylbutenoid dimer analogs
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Several phenylbutenoid dimer (PBD) analogs were synthesized and evaluated for their inhibitory activities against nitric oxide (NO) production and TNF-α release. The PBD analogs were synthesized via Diels - Alder and subsequent Schlosser reactions as key steps. Among the tested compounds, two analogs (8c, 8f) exhibited much stronger inhibitory activity against LPS-stimulated NO production and TNF-α release in RAW 264.7 cells than that of wogonin.
- Kim, Sung-Soo,Fang, Yuanying,Park, Haeil
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p. 1676 - 1680
(2015/07/15)
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- Styrylphenylphthalimides as Novel Transrepression-Selective Liver X Receptor (LXR) Modulators
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Anti-inflammatory effects of liver X receptor (LXR) ligands are thought to be largely due to LXR-mediated transrepression, whereas side effects are caused by activation of LXR-responsive gene expression (transactivation). Therefore, selective LXR modulators that preferentially exhibit transrepression activity should exhibit anti-inflammatory properties with fewer side effects. Here, we synthesized a series of styrylphenylphthalimide analogues and evaluated their structure-activity relationships focusing on LXRs-transactivating-agonistic/antagonistic activities and transrepressional activity. Among the compounds examined, 17l showed potent LXR-transrepressional activity with high selectivity over transactivating activity and did not show characteristic side effects of LXR-transactivating agonists in cells. This representative compound, 17l, was confirmed to have LXR-dependent transrepressional activity and to bind directly to LXRβ. Compound 17l should be useful not only as a chemical tool for studying the biological functions of LXRs transrepression but also as a candidate for a safer agent to treat inflammatory diseases.
- Nomura, Sayaka,Endo-Umeda, Kaori,Aoyama, Atsushi,Makishima, Makoto,Hashimoto, Yuichi,Ishikawa, Minoru
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supporting information
p. 902 - 907
(2015/08/24)
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- Coupling cyclizations with fragmentations for the preparation of heteroaromatics: Quinolines from o-alkenyl arylisocyanides and boronic acids
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Stereoelectronic restrictions on homoallylic ring expansion in alkyne cascades can be overcome by using alkenes as synthetic equivalents of alkynes in reaction cascades that are terminated by C-C bond fragmentation. Implementation of this approach using Mn(iii)-mediated reaction of o-alkenyl isocyanides and boronic acids leads to efficient synthesis of substituted quinolines.
- Evoniuk, Christopher J.,Ly, Michelle,Alabugin, Igor V.
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supporting information
p. 12831 - 12834
(2015/08/06)
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- ALKYLIDINE SUBSTITUTED HETEROCYCLYL DERIVATIVES AS ANTI-BACTERIAL AGENTS
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The present invention relates to alkylidine substituted heterocyclyl derivatives of formula (1) which may be therapeutically useful as as anti-bacterial agents, more particulalrly FabI inhibitors; I in which P, Q, Ri, R2, R3 and "n" have the same meanings given in the specification, and pharmaceutically acceptable salts or pharmaceutically acceptable stereoisomers thereof that are useful in the treatment and prevention in diseases or disorder, in particular their use in diseases or disorder where there is an advantage in inhibiting Enoyl-ACP reductase enzyme (FABI) activity. The present invention also provides methods for synthesizing and administering the FabI inhibitory compounds. The present invention also provides pharmaceutical formulations comprising at least one of the FabI inhibitory compounds together with a pharmaceutically acceptable carrier, diluent or excipient therefor.
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Page/Page column 17
(2015/06/03)
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- ANTI-INVASIVE COMPOUNDS
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The present invention relates to the field of anti-invasive compounds and methods for predicting the anti-invasive activity of said compounds, as well as their use in the prevention and/or treatment of diseases associated with undesired cell invasion; in particular, this invention relates to the field of anti-invasive chalcone-like compounds.
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-
Paragraph 0392-0395
(2015/02/18)
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- Catalytic, oxidant-free, direct olefination of alcohols using Wittig reagents
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Reported here is the catalytic, acceptorless coupling of alcohols with in situ generated, non-stabilized phosphonium ylides to form olefins as major products. The reaction uses low catalyst loadings and does not require added oxidants. Hydrogenation of the product is minimized and the reaction leads to Z (aliphatic) or E (benzylic) stereospecificity.
- Khaskin,Milstein
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supporting information
p. 9002 - 9005
(2015/05/27)
-
- One-pot synthesis of gem-difluorostyrenes from benzyl bromide via olefination of phosphonium ylide with difluorocarbene
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A new approach for the synthesis of gem-difluorostyrenes from benzyl bromide is described. Quaternization of triphenylphosphine with benzyl bromide to give phosphonium salts, deprotonation of the corresponding phosphonium salts to produce phosphonium ylide, and the subsequent olefination of phosphonium ylide with difluorocarbene generated from difluoromethylene phosphobetaine (Ph3P+CF2CO2-) by decarboxylation can occur smoothly in one-pot, furnishing the final gem-difluorostyrenes in good yields.
- Deng, Xiao-Yun,Lin, Jin-Hong,Xiao, Ji-Chang
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p. 116 - 120
(2015/11/10)
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- Synthesis of Two Natural Furan-Cyclized Diarylheptanoids via 2-Furaldehyde
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Two natural diarylheptanoids, 2-benzyl-5-(2-phenylethyl)furan (1) and 2-methoxy-4-{[5-(2-phenylethyl)furan-2-yl]methyl}phenol (2), were synthesized starting from 2-furaldehyde. A Wittig reaction of 2-furaldehyde with benzyltriphenylphosphonium bromide followed by reduction of the alkene C=C bond with Mg gave 2-(2-phenylethyl)furan (5). Lithiation of 5 with BuLi at -78 followed by alkylation with benzyl bromide gave natural product 1. In another approach, Friedel-Crafts acylation of compound 5 with benzoyl chloride followed by deoxygenation of the C=O group afforded 1. The natural product 2 was also synthesized by acylation of 5 with 4-acetoxy-3-methoxybenzoyl chloride (16) followed by deoxygenation and deacetylation.
- Se?inti, Hatice,Se?en, Hasan
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p. 938 - 944
(2015/11/23)
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- Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes
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A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C-C bond cleavage followed by intermolecular [4+2]-Diels-Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist. This journal is
- Mudududdla, Ramesh,Sharma, Rohit,Abbat, Sheenu,Bharatam, Prasad V.,Vishwakarma, Ram A.,Bharate, Sandip B.
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supporting information
p. 12076 - 12079
(2015/02/19)
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- Catalytic asymmetric tamura cycloadditions
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In the presence of a novel, tert-butyl-substituted squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products of significant synthetic interest with excellent enantio- and diastereocontrol. The methodology is of wide scope and encompasses both homophthalic and glutaconic anhydride derivatives, which lead to structurally diverse products. Glutaconic acid-derived anhydrides undergo a clean post-cyclization decarboxylation process which is not a feature of reactions involving homophthalic acid-derived anhydrides. The unusual influence of reaction temperature on diastereocontrol has been probed, with reactions occurring at 30 °C and -30 °C delivering products epimeric at one stereocenter only, in near optical purity. Squared away: The first strategy for bringing about enantioselective Tamura reactions is reported. In the presence of a squaramide-based catalyst, enolizable anhydrides react with alkylidene oxindoles to generate spirooxindole products with excellent enantio- and diastereocontrol. The methodology is of wide scope and leads to structurally diverse products.
- Manoni, Francesco,Connon, Stephen J.
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supporting information
p. 2628 - 2632
(2014/03/21)
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- Facile synthesis of Z -alkenes via uphill catalysis
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Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.
- Singh, Kamaljeet,Staig, Shannon J.,Weaver, Jimmie D.
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supporting information
p. 5275 - 5278
(2014/05/06)
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- Synthesis of novel anticancer agents through opening of spiroacetal ring of diosgenin
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Diosgenin has been modified to furostane derivatives after opening the F-spiroacetal ring. The aldehyde group at C26 in derivative 8 was unexpectedly transformed to the ketone 9. The structure of ketone 9 was confirmed by spectroscopy and finally by X-ray crystallography. Five of the diosgenin derivatives showed significant anticancer activity against human cancer cell lines. The most potent molecule of this series i.e. compound 7, inhibited cellular growth by arresting the population at G0/G1 phase of cell division cycle. Cells undergo apoptosis after exposure to the derivative 7 which was evident by increase in sub G0 population in cell cycle analysis. Docking experiments showed caspase-3 and caspase-9 as possible molecular targets for these compounds. This was further validated by cleavage of PARP, a caspase target in apoptotic pathway. Compound 7 was found non-toxic up to 1000 mg/kg dose in acute oral toxicity in Swiss albino mice.
- Hamid,Hasanain, Mohammad,Singh, Arjun,Bhukya, Balakishan,Omprakash,Vasudev, Prema G.,Sarkar, Jayanta,Chanda, Debabrata,Khan, Feroz,Aiyelaagbe,Negi, Arvind S.
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p. 108 - 118
(2014/07/08)
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- Synthesis of combretastatin A4 analogues on steroidal framework and their anti-breast cancer activity
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Combretastatin A4 analogues were synthesized on steroidal framework from gallic acid with a possibility of anti-breast cancer agents. Twenty two analogues were synthesized and evaluated for cytotoxicity against human breast cancer cell lines (MCF-7 & MDA-MB 231). The best analogue 22 showed potent antitubulin effect. Docking experiments also supported strong binding affinity of 22 to microtubule polymerase. In cell cycle analysis, 22 induced apoptosis in MCF-7 cells significantly. It was found to be non-toxic up to 300 mg/kg dose in Swiss albino mice in acute oral toxicity. This article is part of a Special Issue entitled "Synthesis and biological testing of steroid derivatives as inhibitors".
- Parihar, Swati,Kumar, Amit,Chaturvedi, Amit K.,Sachan, Naresh Kumar,Luqman, Suaib,Changkija, Bendangla,Manohar, Murli,Prakash, Om,Chanda,Khan, Feroz,Chanotiya,Shanker, Karuna,Dwivedi, Anila,Konwar, Rituraj,Negi, Arvind S.
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p. 332 - 344
(2013/11/19)
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- Drawing from a pool of radicals for the design of selective enyne cyclizations
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Despite the possibility of intermolecular attack at four different locations, the Bu3Sn-mediated radical cyclization of aromatic enynes is surprisingly selective. The observed reaction path originates from the least stable of the equilibrating pool of isomeric radicals produced by intermolecular Bu3Sn attack at the π-bonds of substrates. The radical pool components are kinetically self-sorted via 5-exo-trig closure, the fastest of the four possible cyclizations. The resulting Sn-substituted indenes are capable of further transformations in reactions with electrophiles.
- Mondal, Sayantan,Mohamed, Rana K.,Manoharan, Mariappan,Phan, Hoa,Alabugin, Igor V.
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supporting information
p. 5650 - 5653
(2013/12/04)
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- Oxidative cyclizations, the synthesis of aryl-substituted c-glycosides, and the role of the second electron transfer step
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Anodic oxidation reactions have been used to synthesize aryl- and biaryl-substituted C-glycosides. The reactions take advantage of the tendency for alcohol nucleophiles to trap nonpolar radical cations. The addition of the alcohol to the radical cation appears to be reversible, and the success of the cyclizations is dependent on the ease with which the resulting benzylic radical is oxidized.
- Smith, Jake A.,Moeller, Kevin D.
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supporting information
p. 5818 - 5821
(2013/12/04)
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- Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs
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A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5- (hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC 50 = 12 μM). Structure-activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.
- Mohideen, Mazlin,Zulkepli, Suraya,Nik-Salleh, Nik-Salmah,Zulkefeli, Mohd,Weber, Jean-Frédéric Faizal Abdullah,Rahman, A. F. M. Motiur
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p. 812 - 831
(2013/07/26)
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- Design, synthesis and structure-activity relationships of some novel, highly potent anti-invasive (E)- and (Z)-stilbenes
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In our ongoing exploration of the structure-activity landscape of anti-invasive chalcones, we have prepared and evaluated a number of structurally related (E)- and (Z)-stilbenes. These molecules exhibited an extraordinary high in vitro potency in the chick heart invasion assay, being active up to 10 nmol L-1, a concentration level a 100-fold lower than the lowest effective doses that have been reported for natural analogues. Furthermore, they possess an interesting pharmacological profile in silico.
- Roman, Bart I.,De Coen, Laurens M.,Mortier, Séverine Thérèse F.C.,De Ryck, Tine,Vanhoecke, Barbara W.A.,Katritzky, Alan R.,Bracke, Marc E.,Stevens, Christian V.
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p. 5054 - 5063
(2013/09/02)
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- Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols
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Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Additionally, a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reactions steps, the waste toxicity, and the use of costly reagents.
- Chalal, Malik,Vervandier-Fasseur, Dominique,Meunier, Philippe,Cattey, Hélène,Hierso, Jean-Cyrille
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experimental part
p. 3899 - 3907
(2012/07/14)
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- Design, synthesis, and biological activity of a novel series of human sirtuin-2-selective inhibitors
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Selective inhibitors of human sirtuin 2 (SIRT2), a deacetylase, are candidate therapeutic agents for neurodegenerative diseases such as Parkinson's disease and Huntington's disease as well as potential tools for elucidating the biological functions of SIRT2. On the basis of homology models of SIRT1 and SIRT2, we designed and prepared a series of 2-anilinobenzamide analogues. Enzyme assays using recombinant SIRT1 and SIRT2 revealed that 3'-phenethyloxy-2- anilinobenzamide analogues such as 33a and 33i are potent and selective SIRT2 inhibitors, showing more than 3.5-fold greater SIRT2-inhibitory activity and more than 35-fold greater SIRT2-selectivity compared with AGK2 (3), a previously reported SIRT2-selective inhibitor. Compound 33a also induced a dose-dependent selective increase of α-tubulin acetylation in human colon cancer HCT116 cells, indicating selective inhibition of SIRT2 in the cells. These 3'-phenethyloxy-2-anilinobenzamide derivatives represent an entry into a new class of SIRT2-selective inhibitors.
- Suzuki, Takayoshi,Khan, Mohammed Naseer Ahmed,Sawada, Hideyuki,Imai, Erika,Itoh, Yukihiro,Yamatsuta, Katsura,Tokuda, Natsuko,Takeuchi, Jun,Seko, Takuya,Nakagawa, Hidehiko,Miyata, Naoki
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experimental part
p. 5760 - 5773
(2012/07/28)
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- Unequivocal experimental evidence for a unified lithium salt-free wittig reaction mechanism for all phosphonium ylide types: Reactions with β-heteroatom-substituted aldehydes are consistently selective for cis-oxaphosphetane-derived products
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The true course of the lithium salt-free Wittig reaction has long been a contentious issue in organic chemistry. Herein we report an experimental effect that is common to the Wittig reactions of all of the three major phosphonium ylide classes (non-stabilized, semi-stabilized, and stabilized): there is consistently increased selectivity for cis-oxaphosphetane and its derived products (Z-alkene and erythro-β-hydroxyphosphonium salt) in reactions involving aldehydes bearing heteroatom substituents in the β-position. The effect operates with both benzaldehydes and aliphatic aldehydes and is shown not to operate in the absence of the heteroatom substituent on the aldehyde. The discovery of an effect that is common to reactions of all ylide types strongly argues for the operation of a common mechanism in all Li salt-free Wittig reactions. In addition, the results are shown to be most easily explained by the [2+2] cycloaddition mechanism proposed by Vedejs and co-workers as supplemented by Aggarwal, Harvey, and co-workers, thus providing strong confirmatory evidence in support of that mechanism. Notably, a cooperative effect of ortho-substituents in the case of semi-stabilized ylides is confirmed and is accommodated by the cycloaddition mechanism. The effect is also shown to operate in reactions of triphenylphosphine-derived ylides and has previously been observed for reactions under aqueous conditions, thus for the first time providing evidence that kinetic control is in operation in both of these cases.
- Byrne, Peter A.,Gilheany, Declan G.
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supporting information; experimental part
p. 9225 - 9239
(2012/07/14)
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- Ruthenium stilbenyl and diruthenium distyrylethene complexes: Aspects of electron delocalization and electrocatalyzed isomerization of the Z-isomer
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Regio- and stereoselective insertion of the terminal ethynyl functions of 4-ethynylstilbene, the E and Z isomers of 4,4′-bis(ethynylphenyl)ethene and a backbone-rigidified cyclohexenyl derivative of the Z isomer into the Ru-H bond of the complex RuClH(CO)(PiPr3)2 provides the corresponding vinyl ruthenium complexes, which have been characterized spectroscopically and by X-ray crystallography. Large red shifts of the UV/vis absorption bands evidence efficient incorporation of the vinyl metal subunit(s) into the conjugated π-system. All complexes oxidize at low potentials. The various oxidized forms of all complexes were generated and characterized by UV/vis/NIR, IR and EPR spectroscopies. These studies indicated electrocatalytic Z→E isomerization of the oxidized Z-distyrylethene complex Ru-Z2, which is prevented in its backbone-rigidified derivative Ru-Z2fix. The radical cations of the E and the configurationally stable cyclohexene-bridged Z-derivatives are spin-delocalized on the EPR time scale but charge-localized on the faster IR time scale. The degree of ground-state charge delocalization in the mixed-valent state has been quantified by the incremental shifts of the Ru-CO bands upon stepwise oxidation to the radical cations and the dications and was found to be remarkably large (19% and 9%) considering redox splittings ΔE 1/2 of just 49 or 74 mV. Quantum chemical studies with various levels of sophistication reproduce our experimental results including the electronic spectra of the neutral complexes and the intrinsically localized nature of the radical cations of the dinuclear complexes.
- Linseis, Michael,Zalis, Stanislav,Zabel, Manfred,Winter, Rainer F.
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supporting information
p. 16671 - 16692
(2013/01/15)
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- Synthesis of dibenz[a,h]anthracenes by Pd-catalyzed intramolecular double-cyclization of (Z,Z)-p-styrylstilbenes
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Dibenz[a,h]anthracene (1a) and its dimethoxy derivatives 1b and 1c were synthesized by the Pd-catalyzed intramolecular double-cyclization of the corresponding (Z,Z)-p-styrylstilbene derivatives 25, which were readily prepared by the Wittig reaction. The optical properties of the dibenz[a,h]anthracenes 1a1c are also presented.
- Umeda, Rui,Miyake, Satoshi,Nishiyama, Yutaka
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supporting information; experimental part
p. 215 - 217
(2012/05/20)
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- Novel (E)-5-styryl-2,2′-bithiophene derivatives as ligands for β-amyloid plaques
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In continuation of our investigation on the bithiophene structure as potential β-amyloid probes, a series of (E)-5-styryl-2,2′-bithiophene (SBTP) derivatives was designed and synthesized. In vitro binding showed that all of them displayed high binding affinities to Aβ1-42 aggregates (Ki = 0.10-41.05 nM). Moreover, two radio-iodinated probes, [125I]-(E)-5-(4-iodostyryl)-2,2′-bithiophene ([ 125I]8) and [125I]-(E)-5-iodo-5′-(4-methoxystyryl)- 2,2′-bithiophene ([125I]31) were prepared. Both of them displayed specific labeling of Aβ plaques in the brain sections of AD model mice with low background. In vivo biodistribution in normal mice indicated that [125I]8 exhibited high initial brain uptake (2.11% ID/g at 2 min) and rapid clearance (0.41% ID/g at 30 min). These preliminary results suggest that SBTP derivatives may be served as novel β-amyloid imaging probes.
- Cui, Mengchao,Li, Zijing,Tang, Ruikun,Jia, Hongmei,Liu, Boli
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experimental part
p. 2908 - 2916
(2011/07/08)
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