- Carbachol dimers as homobivalent modulators of muscarinic receptors
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A series of homodimers of the well-known cholinergic agonist carbachol have been synthesized, showing the two agonist units symmetrically connected through a methylene chain of variable length. The new compounds have been tested on the five cloned muscarinic receptors (hM1-5) expressed in CHO cells by means of equilibrium binding studies, showing an increase in affinity by rising the number of methylene units up to 7 and 9. Functional experiments on guinea-pig ileum and assessment of ERK1/2 phosphorylation on hM1, hM2 and hM3 on CHO cells have shown that the new compounds are endowed with muscarinic antagonistic properties. Kinetic binding studies have revealed that some of the tested compounds are able to slow the rate of dissociation of NMS, suggesting a bitopic behavior. Docking simulations, performed on the hM1 and hM2 receptors, give a sound rationalization of the experimental data revealing how these compounds are able to interact with both orthosteric and allosteric binding sites depending on the length of their connecting chain.
- Matucci, Rosanna,Nesi, Marta,Martino, Maria Vittoria,Bellucci, Cristina,Manetti, Dina,Ciuti, Elisa,Mazzolari, Angelica,Dei, Silvia,Guandalini, Luca,Teodori, Elisabetta,Vistoli, Giulio,Romanelli, Maria Novella
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Read Online
- Catalytic N-diphosphonomethylation of amino alkanols and bisamino alkanes using tris(trimethylsilyl) phosphite as a convenient synthon
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The new mono- and bis(aminomethylenediphosphonic) acids are synthesized for the first time via unique reaction of tris(trimethylsilyl) phosphite and various N-formyl amino alkanols or bis(N-formyl amino) alkanes at the presence of effective catalyst – trimethylsilyl triflate under mild conditions. The further treatment of initially formed trimethylsilyl intermediates with the methanol excess resulted in the crystalline mono- and bis(aminomethylenediphosphonic) acids in high yields. The catalytic scheme of target substances formation is proposed and discussed in detail. The structures of target acids were confirmed by the 1H, 13C, 31P NMR spectra and high resolution mass spectra (HRMS). The resulting compounds are of great interest as perspective bioactive substances with versatile properties and effective polydentate ligands.
- Prishchenko, Andrey A.,Alekseyev, Roman S.,Novikova, Olga P.,Livantsov, Mikhail V.,Livantsova, Ludmila I.,Petrosyan, Valery S.
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supporting information
(2021/11/09)
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- PROCESS FOR THE PREPARATION OF DI- OR POLYFORMAMIDES
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The invention relates to a process for preparing at least one di- or polyformamide comprising at least two -NHCHO groups by reacting at least one primary di- or polyamine with carbon dioxide in the presence of hydrogen and at least one catalyst selected f
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Page/Page column 8
(2019/06/23)
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- A Combined Photochemical and Multicomponent Reaction Approach to Precision Oligomers
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We introduce the convergent synthesis of linear monodisperse sequence-defined oligomers through a unique approach, combining the Passerini three-component reaction (P-3CR) and a Diels–Alder (DA) reaction based on photocaged dienes. A set of oligomers is prepared resting on a Passerini linker unit carrying an isocyano group for chain extension by P-3CR and a maleimide moiety for photoenol conjugation enabling a modular approach for chain growth. Monodisperse oligomers are accessible in a stepwise fashion by switching between both reaction types. Employing sebacic acid as a core unit allows the synthesis of a library of symmetric sequence-defined oligomers. The oligomers consist of alternating P-3CR and photoblocks with molecular weights up to 3532.16 g mol?1, demonstrating the successful switching from P-3CR to photoenol conjugation. In-depth characterization was carried out including size-exclusion chromatography (SEC), high-resolution electrospray ionization mass spectrometry (ESI-MS) and NMR spectroscopy, evidencing the monodisperse nature of the precision oligomers.
- Konrad, Waldemar,Bloesser, Fabian R.,Wetzel, Katharina S.,Boukis, Andreas C.,Meier, Michael A. R.,Barner-Kowollik, Christopher
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supporting information
p. 3413 - 3419
(2018/02/09)
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- Ru/ceria-catalyzed direct formylation of amines and CO to produce formamides
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We herein report a new strategy of directly converting amines and CO to formamides with 100% atom utilization efficiency. It is suitable for up to 25 amine substrates with no additives. Ru/ceria is found to be an excellent catalyst for this reaction due the efficient co-activation of CO and amine on Ru species.
- Wang, Yehong,Zhang, Jian,Chen, Haijun,Zhang, Zhixin,Zhang, Chaofeng,Li, Mingrun,Wang, Feng
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- An efficient reduction of N-substituted carbonylimidazolides into formamides by NaBH4
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A novel, simple and versatile protocol was investigated for highly efficient synthesis of formamides through reducing N-substituted carbonylimidazolides by NaBH4 under mild reaction conditions. By this method, not only carboxylic acids or isocyanates, but also amines can readily access formamides with high yields.
- Chen, Zhiyong,Cao, Yiming,Tian, Zeyu,Zhou, Xuan,Xu, Wenjin,Yang, Jia,Teng, Hanbing
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p. 2166 - 2170
(2017/05/10)
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- Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
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A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.
- Mampuys, Pieter,Zhu, Yanping,Sergeyev, Sergey,Ruijter, Eelco,Orru, Romano V. A.,Van Doorslaer, Sabine,Maes, Bert U. W.
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supporting information
p. 2808 - 2811
(2016/07/06)
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- C-N and N-H Bond Metathesis Reactions Mediated by Carbon Dioxide
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Herein, we report CO2-mediated metathesis reactions between amines and DMF to synthesize formamides. More than 20 amines, including primary, secondary, aromatic, and heterocyclic amines, diamines, and amino acids, are converted to the corresponding formamides with good-to-excellent conversions and selectivities under mild conditions. This strategy employs CO2 as a mediator to activate the amine under metal-free conditions. The experimental data and in situ NMR and attenuated total reflectance IR spectroscopy measurements support the formation of the N-carbamic acid as an intermediate through the weak acid-base interaction between CO2 and the amine. The metathesis reaction is driven by the formation of a stable carbamate, and a reaction mechanism is proposed.
- Wang, Yehong,Zhang, Jian,Liu, Jing,Zhang, Chaofeng,Zhang, Zhixin,Xu, Jie,Xu, Shutao,Wang, Fangjun,Wang, Feng
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p. 2066 - 2072
(2015/06/30)
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- Transformylating amine with DMF to formamide over CeO2 catalyst
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We here report a new protocol for the formylation of various amines, primary or secondary, aromatic or alkyl, cyclic or linear, mono- or di-amine, with dimethylformamide (DMF) as the formylation reagent to obtain the corresponding formamides in good to excellent yields over CeO2 catalyst. The reaction requires no homogeneous acidic or basic additives and is tolerant to water.
- Wang, Yehong,Wang, Feng,Zhang, Chaofeng,Zhang, Jian,Li, Mingrun,Xu, Jie
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supporting information
p. 2438 - 2441
(2014/03/21)
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- Synthesis and antiproliferative activity of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids
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A series of aromatic and aliphatic bis[aminomethylidene(bisphosphonic)] acids was synthesized in the reaction of triethylphosphite with isonitriles followed by hydrolysis or dealkylation. The in vitro anti-proliferative effect of all synthesized tetraphosphonic acids against MCF-7 breast cancer cells, J774E macrophages and HL-60 promyelocytic leukemia cells was determined. Three aromatic derivatives (5a, 5f and 5j) showed a similar or higher anti-proliferative activity than zoledronic acid.
- Goldeman, Waldemar,Nasulewicz-Goldeman, Anna
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supporting information
p. 3475 - 3479
(2014/07/22)
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- Multicomponent synthesis of artificial nucleases and their RNase and DNase activity
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The synthesis of new, artificial ribonucleases containing two amino acid residues connected by an aliphatic linker has beendeveloped. Target molecules were synthesized via a catalytic three-component Ugi reaction from aliphatic diisocyanides. Preliminaryinvestigations proved unspecific nuclease activity of the new compounds towards single-stranded RNA and doublestrandedcircular DNA .
- Gulevich, Anton V.,Nenajdenko, Valentine G.,Koroleva, Lyudmila S.,Morozova, Olga V.,Silnikov, Vladimir N.,Bakhvalova, Valentina N.
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supporting information; experimental part
p. 1135 - 1140
(2011/10/19)
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- Stereoselective aldol additions of achiral ethyl ketone-derived trichlorosilyl enolates
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Methods for the preparation of geometrically defined enoxy(trichlorosilanes) derived from ethyl ketone enolates have been developed. The addition of enoxy(trichlorosilanes) (trichlorosilyl enolates) to aldehydes proceeds with good yields in the presence of catalytic amounts of chiral phosphoramides. The reaction of Z-trichlorosilyl enolates to aryl aldehydes affords aldol products with good to excellent diastereo- and enantioselectivities. Phosphoramide-catalyzed aldol additions lacked substrate generality providing modest selectivities with unsaturated and aliphatic aldehydes. In all cases, the phosphoramide-catalyzed aldol addition of E-trichlorosilyl enolates to aldehydes provided good yields with moderate to good stereoselectivities.
- Denmark, Scott E.,Pham, Son M.
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p. 5045 - 5055
(2007/10/03)
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- A novel PdCl2/ZrO2-SO42- catalyst for synthesis of carbamates by oxidative carbonylation of amines
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At 170°C and ca. 4.0 MPa, oxidative carbonylation of aromatic amines to synthesize corresponding carbamates over a novel PdCl2/ZrO2-SO42- catalyst could proceed with high conversion and selectivity.
- Shi, Feng,Deng, Youquan,SiMa, Tianlong,Yang, Hongzhou
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p. 525 - 528
(2007/10/03)
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- The first syntheses of diformamides by carbonylation of aliphatic diamines with Au(I) complex catalysts
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Organic Au(I) complexes could be highly effective catalysts for the synthesis of diformamides by carbonylation of aliphatic diamines, with selectivity significantly enhanced in the presence of the appropriate amount of oxygen.
- Shi,Deng,Yang,SiMa
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p. 345 - 346
(2007/10/03)
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- First gold(I) complex-catalyzed oxidative carbonylation of amines for the syntheses of carbamates
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At 200 °C and 5 MPa of initial total pressure, the oxidative carbonylation of amines for the synthesis of the corresponding carbamates by Au(I) complexes as catalysts was conducted with excellent conversion and selectivity.
- Shi,Deng
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p. 443 - 444
(2007/10/03)
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- A Simple and Economic Synthesis of Monoacylated Alkanediamines by Thermal Transamidation
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N-(ω-Aminoalkyl)amides 2 are easily synthesized by heating mixtures of excess α,ω-alkanediamines 1 and primary amides to temperatures between 150 deg C and 200 deg C, at which thermal transamidation occurs.Under the reaction conditions ammonia is released, and 2 is in equilibrium with the alkanediamine 1 and the α,ω-bis(acylamino)alkane 3.Thus, thermal transamidation is a practicable way to overcome the problem of diacylation which appears as an often recognized problem even in the latest literature.
- Zaragoza-Doerwald, Florencio,Kiedrowski, Guenter von
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p. 917 - 918
(2007/10/02)
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