- Intramolecular Electron Transfer and SN2 Reactions in the Radical Anions of 1-(4-Biphenylyl)-ω-haloalkane Studied by Pulse Radiolysis
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One-electron reduction of 1-(4-biphenylyl)-ω-haloalkane (BPX-n) by solvated electrons and the intramolecular reactions of the radical anion thus formed have been investigated using the pulse-radiolysis technique.The spectrum observed immediately after the pulse has an absorption maximum at 410 nm which is assigned to the corresponding biphenyl radical anion.The decay behavior of all these 410-nm bands follows first-order kinetics and the rates are dependent on the methylene chain length, n.With BPCl-0 and BPCl-2, which provide large rate constants (7.5E7 and 1.7E8 s-1, respectively) and large G values of 4-alkylbiphenyl formation, an intramolecular electron transfer from a biphenyl radical anion to a C-Cl bond is presumed.The rate constants of the radical anions decrease in the order BPCl-1 > BPCl-2 > BPCl-0 which is roughly parallel to the C-Cl bond energy of these compounds and does not correlate with the chain length n, which corresponds to the distance required for the electron transfer.On the other hand, in the case of BPCl-3 and BPCl-4, the decay of the 410-nm band decreased about two orders of magnitude (5.5E5 and 1.2E6 s-1, respectively) and was characterized by a simultanous formation of a 330-nm band which is assigned to a spirocyclic radical.The G values of the corresponding 4-alkylbiphenyl formation were low for these compounds.On the basis of these observations, an intramolecular carbanionic displacement of the biphenyl radical anion on the chlorine center, which is a novel type of intramolecular SN2 reaction, has been concluded.Intramolecular reactions of bromo and iodo derivatives were also investigated and compared with those of corresponding chlorides.
- Kigawa, Hitoshi,Takamuku, Setsuo,Toki, Susumu,Kimura, Norio,Takeda, Seishi,et al.
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Read Online
- Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia
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Recently, irreversible inhibitors have attracted great interest in antitumors due to their advantages of forming covalent bonds to target proteins. Herein, some benzothiazepinone compounds (BTZs) have been designed and synthesized as novel covalent GSK-3β inhibitors with high selectivity for the kinase panel. The irreversible covalent binding mode was identified by kinetics and mass spectrometry, and the main labeled residue was confirmed to be the unique Cys14 that exists only in GSK-3β. The candidate 4-3 (IC50 = 6.6 μM) showed good proliferation inhibition and apoptosis-inducing ability to leukemia cell lines, low cytotoxicity on normal cell lines, and no hERG inhibition, which hinted the potential efficacy and safety. Furthermore, 4-3 exhibited decent pharmacokinetic properties in vivo and remarkably inhibited tumor growth in the acute promyelocytic leukemia (APL) mouse model. All the results suggest that these newly irreversible BTZ compounds might be useful in the treatment of cancer such as APL.
- Zhang, Peng,Min, Zhihui,Gao, Yang,Bian, Jiang,Lin, Xin,He, Jie,Ye, Deyong,Li, Yilin,Peng, Chao,Cheng, Yunfeng,Chu, Yong
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p. 7341 - 7358
(2021/06/28)
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- Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
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Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.
- Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie
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supporting information
p. 8829 - 8842
(2021/06/30)
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- Photo-Promoted Decarboxylative Alkylation of α, β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β, γ-Unsaturated Nitriles
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An efficient, catalyst/photocatalyst-free, and cost-effective methodology for the decarboxylative alkylation of α,β-unsaturated carboxylic acids to synthesize β,γ-unsaturated nitriles has been developed. The reaction proceeded in an environmentally benign atmosphere of blue light-emitting diode irradiation with K2CO3 and water at room temperature. The methodology worked for a wide range of substrates (22 examples) with up to 83% yield. The protocol is also compatible for gram-scale synthesis.
- Pan, Chunxiang,Yang, Chunhui,Li, Kangkui,Zhang, Keyang,Zhu, Yuanbin,Wu, Shiyuan,Zhou, Yongyun,Fan, Baomin
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supporting information
p. 7188 - 7193
(2021/10/01)
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- Method for preparing alpha, beta-unsaturated carboxylic acid compound
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The invention discloses a method for preparing an alpha, beta-unsaturated carboxylic acid compound, which comprises the following steps: 1) in an atmosphere containing carbon dioxide, heating and reacting a mixture containing hydrosilane and a copper catalyst to obtain a system I; and 2) adding a raw material containing alkyne and a nickel catalyst into the system I in the step 1), and heating to react. The method has the advantages of simple, easily available, cheap and stable raw materials, common, easily available and stable catalyst, mild reaction conditions, simple post-treatment, high yield and the like.
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Paragraph 0103-0104; 0479-0494
(2021/05/05)
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- Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst
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We have developed an efficient photocatalytic synthesis of coumarin derivativesviaa tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives dimerized lignan-type products.
- Zhao, Bin,Xu, Bo
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supporting information
p. 568 - 573
(2021/02/06)
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- The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo
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The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiology approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, A23 was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury.
- Zhang, Han,Yu, Peilin,Lin, Hongwei,Jin, Zefang,Zhao, Siqi,Zhang, Yi,Xu, Qingxia,Jin, Hongwei,Liu, Zhenming,Yang, Wei,Zhang, Liangren
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p. 3976 - 3996
(2021/05/04)
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- Water-initiated hydrocarboxylation of terminal alkynes with CO2and hydrosilane
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This work discloses a Cu(ii)-Ni(ii) catalyzed tandem hydrocarboxylation of alkynes with polysilylformate formed from CO2and polymethylhydrosiloxane that affords α,β-unsaturated carboxylic acids with up to 93% yield. Mechanistic studies indicate that polysilylformate functions as a source of CO and polysilanol. Besides, a catalytic amount of water is found to be critical to the reaction, which hydrolyzes polysilylformate to formic acid that induces the formation of Ni-H active species, thereby initiating the catalytic cycle.
- Wang, Meng-Meng,Lu, Sheng-Mei,Paridala, Kumaraswamy,Li, Can
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supporting information
p. 1230 - 1233
(2021/02/09)
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- Carboxylation of Alkenyl Boronic Acids and Alkenyl Boronic Acid Pinacol Esters with CO2 Catalyzed by Cuprous Halide
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A cuprous halide catalysed carboxylation of alkenyl boronic acids and alkenyl boronic acid pinacol esters under CO2, affording the corresponding α, β-unsaturated carboxylic acids in good yield, has been developed. The potassium (E)-trifluoro(styryl)borate is also compatible with this reaction. This simple and efficient copper(I) catalytic system showed good functional group tolerance.
- Hong, Junting,Nayal, Onkar S.,Mo, Fanyang
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supporting information
p. 2813 - 2818
(2020/05/16)
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- Method for preparing alpha, beta-unsaturated carboxylic acid by reacting alkenyl boron compound with carbon dioxide under catalysis of cuprous halide
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The invention discloses a method for preparing alpha, beta-unsaturated carboxylic acid through a carboxylation reaction of an alkenyl boron compound and carbon dioxide under the catalysis of cuprous halide. According to the method, carbon dioxide is used as a C1 source, the cuprous halide is adopted for catalysis, and alkoxide serves as alkali to react in an organic solvent, so the method is simple and easy to implement, has a wide substrate application range, converts various alkenyl boron compounds such as alkenyl boric acid, alkenyl borate and borate into corresponding alpha, beta-unsaturated carboxylic acid under mild conditions, and has a very high yield. The obtained product alpha, beta-unsaturated carboxylic acid is an important intermediate for preparing fine chemical products suchas perfumes, insecticides and the like.
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Paragraph 0049-0050
(2020/06/17)
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- Electrical properties of amino acid substituted novel cinnamic acid compounds
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Amino acid conjugates are combinations of one or more compounds, at least one of them active in terms of biological, pharmacological or physical. In this work, some novel amino acid conjugates, four different aldehydes (Pyrene, Naphthalene, Phenanthrene and Phenyl benzyl) have been chosen and from these initial materials four different amino acid conjugates were synthesized. The compounds from initial steps to final steps have been characterized by 1H and 13C APT NMR spectroscopy. The dielectric measurements were done by QuadTech 7600 LRC impedance analyzer. The dielectric constant (ε′) dielectric loss (ε’’) and ac conductivity (σ) values of amino acid conjugates in the frequency of 1 kHz and at 25 °C. The results show that the increase in conjugation affect the dielectric constant and conductivity.
- ?al??kan, Eray,?etin, Ahmet,G?rgülü, Ahmet Orhan,Koran, Kenan
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- Acrylamide benzoazepine derivatives as GSK-3beta inhibitors and applications thereof
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The invention belongs to the technical field of medicinal chemistry, and discloses acrylamide benzoazepine derivatives serving as glycogen synthase kinase-3beta (GSK-3beta) inhibitors and applicationsof the acrylamide benzoaza derivatives. The derivatives are compounds shown as a formula (I) or pharmaceutically acceptable salts thereof. The compounds have good inhibitory activity on GSK-3beta andcan be used as selective inhibitors for preventing and treating GSK-3beta-related diseases, and the GSK-3beta-related diseases include cancer, neurodegenerative diseases and diabetes.
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Paragraph 0051-0054; 0057-0059
(2020/11/26)
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- Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids
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A Pd-catalyzed decarboxylative cross-coupling of α,β-unsaturated carboxylic acids with cyclic and acyclic epoxides has been developed. Both β-monosubstituted and β-disubstituted unsaturated carboxylic acids, as well as conjugated diene unsaturated carboxylic acids are suitable reaction substrates. Substituted homoallylic alcohols were obtained in moderate to good yields. The product was obtained as a mixture of diastereomers favoring the anti diastereomer of the cyclic epoxides. This work provides a method for the modification of complex organic molecules containing α,β-unsaturated carboxylic acids.
- Lu, Xiao-Yu,Li, Jin-Song,Wang, Shi-Qun,Zhu, Yu-Jing,Li, Yue-Ming,Yan, Lu-Yu,Li, Jia-Mei,Wang, Jin-Yu,Zhou, Hai-Pin,Ge, Xiu-Tao
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supporting information
p. 11123 - 11126
(2019/09/20)
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- Synthesis, biological evaluation, and structure activity relationship (SAR) study of pyrrolidine amide derivatives as: N -acylethanolamine acid amidase (NAAA) inhibitors
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N-Acylethanolamine acid amidase (NAAA) is one of the key enzymes involved in the degradation of fatty acid ethanolamides (FAEs), especially for palmitoylethanolamide (PEA). Pharmacological blockage of NAAA restores PEA levels, providing therapeutic benefits in the management of inflammation and pain. In the current work, we showed the structure-activity relationship (SAR) studies for pyrrolidine amide derivatives as NAAA inhibitors. A series of aromatic replacements or substituents for the terminal phenyl group of pyrrolidine amides were examined. SAR data showed that small lipophilic 3-phenyl substituents were preferable for optimal potency. The conformationally flexible linkers increased the inhibitory potency of pyrrolidine amide derivatives but reduced their selectivity toward fatty acid amide hydrolase (FAAH). The conformationally restricted linkers did not enhance the inhibitor potency toward NAAA but improved the selectivity over FAAH. Several low micromolar potent NAAA inhibitors were developed, including 4g bearing a rigid 4-phenylcinnamoyl group. Dialysis and kinetic analysis suggested that 4g inhibited NAAA via a competitive and reversible mechanism. Furthermore, 4g showed high anti-inflammatory activities in lipopolysaccharide (LPS) induced acute lung injury (ALI) model, and this effect was blocked by pre-treatment with the PPAR-α antagonist MK886. We anticipate that 4g (E93) will enable a new agent to treat inflammation and related diseases.
- Zhou, Pan,Xiang, Lei,Zhao, Dongsheng,Ren, Jie,Qiu, Yan,Li, Yuhang
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supporting information
p. 252 - 262
(2019/03/02)
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- Tailored Mutants of Phenylalanine Ammonia-Lyase from Petroselinum crispum for the Synthesis of Bulky l- and d-Arylalanines
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Tailored mutants of phenylalanine ammonia-lyase from Petroselinum crispum (PcPAL) were created and tested in ammonia elimination from various sterically demanding, non-natural analogues of phenylalanine and in ammonia addition reactions into the corresponding (E)-arylacrylates. The wild-type PcPAL was inert or exhibited quite poor conversions in both reactions with all members of the substrate panel. Appropriate single mutations of residue F137 and the highly conserved residue I460 resulted in PcPAL variants that were active in ammonia elimination but still had a poor activity in ammonia addition onto bulky substrates. However, combined mutations that involve I460 besides the well-studied F137 led to mutants that exhibited activity in ammonia addition as well. The synergistic multiple mutations resulted in substantial substrate scope extension of PcPAL and opened up new biocatalytic routes for the synthesis of both enantiomers of valuable phenylalanine analogues, such as (4-methoxyphenyl)-, (napthalen-2-yl)-, ([1,1′-biphenyl]-4-yl)-, (4′-fluoro-[1,1′-biphenyl]-4-yl)-, and (5-phenylthiophene-2-yl)alanines.
- Filip, Alina,Nagy, Emma Z. A.,Tork, Souad D.,Bánóczi, Gergely,To?a, Monica I.,Irimie, Florin D.,Poppe, László,Paizs, Csaba,Bencze, László C.
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p. 2627 - 2633
(2018/05/03)
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- Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus
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Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus.
- Giancotti, Gilda,Cancellieri, Michela,Balboni, Andrea,Giustiniano, Mariateresa,Novellino, Ettore,Delang, Leen,Neyts, Johan,Leyssen, Pieter,Brancale, Andrea,Bassetto, Marcella
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supporting information
p. 56 - 68
(2018/03/06)
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- Discovery and anti-inflammatory evaluation of benzothiazepinones (BTZs) as novel non-ATP competitive inhibitors of glycogen synthase kinase-3β (GSK-3β)
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Glycogen synthase kinase-3β (GSK-3β) has been identified to promote inflammation and its inhibitors have also been proven to treat some inflammatory mediated diseases in animal models. Non-ATP competitive inhibitors inherently have better therapeutical value due to their higher specificity than ATP competitive ones. In this paper, we designed and synthesized a series of new BTZ derivatives as non-ATP competitive GSK-3β inhibitors. Kinetic analysis revealed two typical compounds 6j and 3j showed the different non-ATP competitive mechanism of substrate competition or allosteric modulation to GSK-3β, respectively. As expected, the two compounds showed good specificity in a panel test of 16 protein kinases, even to the closest enzymes, like CDK-1/cyclin B and CK-II. The in vivo results proved that both compounds can greatly attenuate the LPS-induced acute lung injury (ALI) and diminish inflammation response in mice by inhibiting the mRNA expression of IL-1β and IL-6. Western blot analysis demonstrated that they negatively regulated GSK-3β, and the mechanism of the observed beneficial effects of the inhibitors may involve both the increased phosphorylation of the Ser9 residue on GSK-3β and protein expression of Sirtuin 1 (SIRT1). The results support that such novel BTZ compounds have a protective role in LPS-induced ALI, and might be attractive candidates for further development of inflammation pharmacotherapy, which greatly thanks to their inherently high selectivities by the non-ATP competitive mode of action. Finally, we proposed suggesting binding modes by Docking study to well explain the impacts of compounds on the target site.
- Gao, Yang,Zhang, Peng,Cui, Anfeng,Ye, De-Yong,Xiang, Meng,Chu, Yong
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p. 5479 - 5493
(2018/10/09)
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- Transition-metal-free C-P bond formation via decarboxylative phosphorylation of cinnamic acids with P(O)H compounds
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A novel, transition-metal-free phosphorylation of cinnamic acids with P(O)H compounds has been developed via radical-promoted decarboxylation under mild conditions. This method provides simple, efficient, and versatile access to valuable (E)-alkenylphosphine oxides in satisfactory yields with a wide variety of substrates.
- Liu, Lixin,Zhou, Dan,Dong, Jianyu,Zhou, Yongbo,Yin, Shuang-Feng,Han, Li-Biao
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p. 4190 - 4196
(2018/04/14)
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- Carboxylation of styrenes with CBr4 and DMSO via cooperative photoredox and cobalt catalysis
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Cooperative photoredox and cobalt catalyzed carboxylation of styrenes with CBr4 to afford the corresponding α,β-unsaturated carboxylic acids has been realized through radical addition and Kornblum (DMSO) oxidation. DMSO serves as the oxidant, oxygen source and solvent under these photocatalytic conditions.
- Song, Cai-Xia,Chen, Ping,Tang, Yu
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p. 11233 - 11243
(2017/02/26)
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- Chemoenzymatic Synthesis of Optically Pure l- and d-Biarylalanines through Biocatalytic Asymmetric Amination and Palladium-Catalyzed Arylation
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A chemoenzymatic approach was developed and optimized for the synthesis of a range of N-protected nonnatural l- and d-biarylalanine derivatives. Starting from 4-bromocinnamic acid and 4-bromophenylpyruvic acid using a phenylalanine ammonia lyase (PAL) and an evolved d-amino acid dehydrogenase (DAADH), respectively, both enantiomers of 4-bromophenylalanine were obtained and subsequently coupled with a panel of arylboronic acids to give the target compounds in high yield and optical purity under mild aqueous conditions.
- Ahmed, Syed T.,Parmeggiani, Fabio,Weise, Nicholas J.,Flitsch, Sabine L.,Turner, Nicholas J.
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p. 5410 - 5413
(2015/09/15)
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- TiCl4-mediated olefination of aldehydes with acetic acid and alkyl acetates: A stereoselective approach to (E)-α,β-unsaturated carboxylic acids and esters
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A new method has been developed for the preparation of α,β- unsaturated carboxylic acids and corresponding esters with (E)-stereoselectivity via the TiCl4-mediated olefination of aldehydes. The method, which uses readily available acetic acid or its alkyl esters as active methylene partners, is more flexible and complementary to conventional routes in the preparation of (E)-cinnamic acid derivatives.
- Augustine, John Kallikat,Boodappa, Chandrakantha,Venkatachaliah, Srinivasa,Mariappan, Ayyampillai
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p. 3503 - 3506
(2014/06/10)
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- Synthesis, molecular modeling and biological evaluation of β-ketoacyl-acyl carrier protein synthase III (FabH) as novel antibacterial agents
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A series of novel cinnamic acid secnidazole ester derivatives have been designed and synthesized, and their biological activities were also evaluated as potential inhibitors of FabH. These compounds were assayed for antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus. Compounds with potent antibacterial activities were tested for their E. coli FabH inhibitory activity. Compound 3n showed the most potent antibacterial activity with MIC of 1.56-6.25 μg/mL against the tested bacterial strains and exhibited the most potent E. coli FabH inhibitory activity with IC50 of 2.5 μM. Docking simulation was performed to position compound 3n into the E. coli FabH active site to determine the probable binding conformation.
- Zhang, Hong-Jia,Zhu, Di-Di,Li, Zi-Lin,Sun, Juan,Zhu, Hai-Liang
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experimental part
p. 4513 - 4519
(2011/09/12)
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- Synthesis, molecular modeling, and biological evaluation of cinnamic acid metronidazole ester derivatives as novel anticancer agents
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A series of novel cinnamic acid metronidazole ester derivatives have been designed and synthesized, and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Compound 3h showed the most potent biological activity (IC50 = 0.62 μM for EGFR and IC50 = 2.15 μM for HER-2). Docking simulation was performed to position compound 3h into the EGFR active site to determine the probable binding model. Antiproliferative assay results demonstrated that some of these compounds possessed good antiproliferative activity against MCF-7. Compound 3h with potent inhibitory activity in tumor growth inhibition may be a potential anticancer agent.
- Qian, Yong,Zhang, Hong-Jia,Zhang, Hao,Xu, Chen,Zhao, Jing,Zhu, Hai-Liang
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experimental part
p. 4991 - 4996
(2010/09/05)
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- Traceless sulfone linker cleavage triggered by ozonolysis: solid-phase synthesis of diverse α-β-unsaturated carbonyl compounds
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The highly efficient and convenient protocol to prepare diverse α,β-unsaturated aldehydes, ketones, and acids via the parallel solid-phase synthesis is developed. The key sulfone linker cleavage strategy is performed by ozonolysis to generate a carbonyl moiety followed by base-mediated polymer-bound sulfinate elimination to release our desired molecules from the resin. All α,β-unsaturated carbonyl compounds are prepared in good purities and yields without further purification.
- Chang, Yi-Fan,Jiang, Yi-Rui,Cheng, Wei-Chieh
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p. 543 - 547
(2008/04/13)
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- AROMATIC DIAMINES WITH A PHOTOREACTIVE AROMATIC SIDE GROUP, POLYAMIC ACID PHOTO-ALIGNMENT LAYERS WITH THEM AND METHOD FOR PREPARING LIQUID CRYSTAL CELLS
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The present invention relates to photo-alignment layers from polyamic acid with a photoreactive aromatic side group. More specifically, the present invention relates to novel polyamic acid photo-alignment layers prepared by the solution polymerization of acid dianhydrides which comprises alicyclic acid dianhydrides at certain ratio or more and aromatic diamines which comprises aromatic diamines with a photoreactive aromatic side group at certain ratio or more and the preparation method thereof, and the preparation method of aromatic diamines with novel aromatic side group. Said polyamic acid photo-alignment layers provide excellent heat- resistance, surface hardness, transparency and liquid crystal alignment property for polarized UV light.
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Page/Page column 14
(2009/01/24)
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- Substituted aryloximes
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The present invention relates to substituted aryl oximes and methods of using them.
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Page/Page column 25
(2010/02/11)
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- The discovery and synthesis of novel adenosine receptor (A2A) antagonists
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In high throughput screening of our file compounds, a novel structure 1 was identified as a potent A2A receptor antagonist with no selectivity over the A1 adenosine receptor. The structure-activity relationship investigation using 1 as a template lead to identification of a novel class of compounds as potent and selective antagonists of A2A adenosine receptor. Compound 26 was identified to be the most potent A2A receptor antagonist (Ki = 0.8 nM) with 100-fold selectivity over the A1 adenosine receptor.
- Matasi, Julius J.,Caldwell, John P.,Hao, Jinsong,Neustadt, Bernard,Arik, Leyla,Foster, Carolyn J.,Lachowicz, Jean,Tulshian, Deen B.
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p. 1333 - 1336
(2007/10/03)
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- A one-pot synthesis of 3-amino-3-arylpropionic acids
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3-Aminopropionic acids (β-amino acids) are biologically active compounds of interest in medicinal and pharmaceutical chemistry. Twenty-one 3-amino-3-arylpropionic acids were synthesized via a facile one-pot synthesis. In addition, a series of mechanistic studies have been performed to optimize the production of these β-amino acids. The reaction mechanism of this one-pot synthesis of β-amino acids, as well as the electronic effect of para-substitution and the influence of solvent polarity on the proposed reaction mechanism are discussed.
- Tan,Weaver
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p. 7449 - 7461
(2007/10/03)
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- Synthetic studies of novel ninhydrin analogs
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Ninhydrin is an essential tool in the analysis of amino acids, peptides, and proteins, and the preferred reagent for the detection of latent fingerprints on porous surfaces. The goal of this investigation was to prepare ninhydrin analogs with enhanced chromogenic and fluorogenic properties. Target compounds included structures with extended conjugation and (or) with the presence of sulfur-containing moieties. We have devised general convergent routes for novel heterocyclic and aryl-substituted ninhydrin analogs for use as reagents for amino acid detection.
- Hark, Richard R.,Hauze, Diane B.,Petrovskaia, Olga,Joullie, Madeleine M.
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p. 1632 - 1654
(2007/10/03)
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- Efficient asymmetric synthesis of the four diastereomers of diphenacoum and brodifacoum
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A highly stereo- and enantio-selective approach to the four stereoisomers of the rodenticides, diphenacoum and brodifacoum, is described. The key step involves the stereospecific formation of one of the crucial bonds in the molecular backbone, and is based on asymmetric organocopper 1,4-addition to chiral imides. Intramolecular cyclization of the resulting butanoate and coupling with 4-hydroxycoumarin, afford the title compounds.
- Van Heerden, Pieter S.,Bezuidenhoudt, Barend C.B.,Ferreira, Daneel
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p. 6045 - 6056
(2007/10/03)
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- SUBSTITUTED HYDROXYUREAS
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The present invention relates to substituted hydroxyureas. These compounds inhibit the enzyme 5-lipoxygenase. In addition, certain of the compounds also inhibit the enzyme-cyclooxygenase. The compounds are useful for treating asthma, allergies, arthritis, posoriasis, ischemia, dermatitis, inflammation and/or broncho-constriction and/or inflammatory diseases of the eye.
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- Lipoxygenase inhibiting compounds
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Compounds of the formula STR1 where R1 is a trinuclear aromatic or biaryl group; R2 is hydrogen or C1 to C6 alkyl or cycloalkyl; n is 0 or 1; and M is a pharmaceutically acceptable cation, are potent inhibitors of the enzymes 5-, 12-, and 15-lipoxygenase.
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