- Synthesis of C-carbamoyl-1,2,3-triazoles by microwave-induced 1,3-dipolar cycloaddition of organic azides to acetylenic amides
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1,3-Dipolar cycloaddition of organic azides 1, 2, or 3 to acetylenic amides 4 or 5 under solvent-free microwave irradiation produced the corresponding N-substituted C-carbamoyl-1,2,3-triazoles 7a-12a in good to excellent yields. Under similar reaction conditions, 1,3-dipolar cycloaddition of diazide 6 and acetylenic amide 4 gave the azido-triazole 13a.
- Katritzky, Alan R.,Singh, Sandeep K.
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Read Online
- New alkyne esters and alkyneamide plant antibacterial agents
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The present invention relates to a class of propyne esters and propyneamide compounds and synthetic methods thereof, and drugs containing the compound and applications thereof. The two types of compounds have efficient and broad-spectrum inhibitory activity for more than ten kinds of plant pathogenic fungi, and at the same time have the characteristics of simple structure, easy large-scale preparation and high safety of animals and plants, and can be used as active ingredients for the development of new plant antibacterial agents with high efficiency and low toxicity.
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Paragraph 0059-0062; 0079
(2022/03/02)
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- Optimized aqueous Kinugasa reactions for bioorthogonal chemistry applications
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Kinugasa reactions hold potential for bioorthogonal chemistry in that the reagents can be biocompatible. Unlike other bioorthogonal reaction products, β-lactams are potentially reactive, which can be useful for synthesizing new biomaterials. A limiting factor for applications consists of slow reaction rates. Herein, we report an optimized aqueous copper(i)-catalyzed alkyne-nitrone cycloaddition involving rearrangement (CuANCR) with rate accelerations made possible by the use of surfactant micelles. We have investigated the factors that accelerate the aqueous CuANCR reaction and demonstrate enhanced modification of a model membrane-associated peptide. We discovered that lipids/surfactants and alkyne structure have a significant impact on the reaction rate, with biological lipids and electron-poor alkynes showing greater reactivity. These new findings have implications for the use of CuANCR for modifying integral membrane proteins as well as live cell labelling and other bioorthogonal applications.
- Bilodeau, Didier A.,Margison, Kaitlyn D.,Ahmed, Noreen,Strmiskova, Miroslava,Sherratt, Allison R.,Pezacki, John Paul
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supporting information
p. 1988 - 1991
(2020/02/25)
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- BTK Inhibitors and uses thereof
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The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.
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Paragraph 1142-1147
(2020/05/02)
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- IODINE RADIOLABELLING METHOD
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The present invention provides a novel method of labelling biological targeting molecules (BTMs) of interest with radioiodine. Also provided are novel radioiodinated BTMs prepared using the method, as well as radiopharmaceutical compositions comprising su
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- Merging allosteric and active site binding motifs: De novo generation of target selectivity and potency via natural-product-derived fragments
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The de novo design of molecules from scratch with tailored biological activity is still the major intellectual challenge in chemical biology and drug discovery. Herein we validate natural-product-derived fragments (NPDFs) as excellent molecular seeds for the targeted de novo discovery of lead structures for the modulation of therapeutically relevant proteins. The application of this de novo approach delivered, in synergy with the combination of allosteric and active site binding motifs, highly selective and ligand-efficient non-zinc-binding (3 : 4-{[5-(2-{[(3-methoxyphenyl)methyl]carbamoyl}eth-1-yn-1-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]methyl}benzoic acid) as well as zinc-binding (4: 4-({5-[2-({[3-(3-carboxypropoxy)phenyl]methyl}-carbamoyl)eth-1-yn-1-yl]-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl}methyl)benzoic acid) uracil-based MMP-13 inhibitors presenting IC50 values of 11 nM (3: LE = 0.35) and 6 nM (4: LE = 0.31).
- Lanz, Jan,Ried, Rainer
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supporting information
p. 451 - 454
(2015/03/18)
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- Direct amidation from alcohols and amines through a tandem oxidation process catalyzed by heterogeneous-polymer-incarcerated gold nanoparticles under aerobic conditions
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We describe herein a highly elegant and suitable synthesis of amide products from alcohols and amines through a tandem oxidation process that uses molecular oxygen as a terminal oxidant. Carbon-black-stabilized polymer-incarcerated gold (PICB-Au) or gold/cobalt (PICB-Au/Co) nanoparticles were employed as an efficient heterogeneous catalyst depending on alcohol reactivity and generated only water as the major co-product of the reaction. A wide scope of substrate applicability was shown with 42 examples. The catalysts could be recovered and reused without loss of activity by using a simple operation. Gold standard: A highly efficient green method for amide synthesis from alcohols and amines catalyzed by gold nanoparticles stabilized by styrene-based copolymers has been developed (see scheme). Two catalysts have been used with high selectivity depending on the combination of substrates. These Au nanoparticle catalysts can be recovered and reused several times by simple operations. Copyright
- Soule, Jean-Francois,Miyamura, Hiroyuki,Kobayashi, Shu
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supporting information
p. 2614 - 2626
(2013/11/19)
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- PROCESS FOR PRODUCING RADIOHALOGENATED BIOCONJUGATES AND PRODUCTS THEREOF
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The present invention relates to a new synthetic process in which an alkyne and an azide react to form a radioisotopic bioconjugate construct. The reaction is particularly useful for producing compounds for use in imaging and radiotherapy applications. The present invention also provides bioconjugate labels and further relates to the use of these compounds in diagnostic and therapeutic methods. In addition, the invention provides a related process for introducing a radioisotopic halogen atom into a terminal alkyne.
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Paragraph 0247; 0248
(2013/08/28)
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- Selectivity control by silver catalysts in the cycloisomerization of 1,6-enynes derived from propiolamides
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Silver-catalyzed cycloisomerizations of 1,6-enynes derived from propiolamides led to a selective formation of Alder-ene type 1,4-dienes. Interestingly, AgNTf2 outperformed gold or platinum catalysts in terms of selectivity and reactivity, providing the 1,4-dienes at room temperature. The presence of C(5) carbonyl group in combination with Ag salts is key to the selectivity and the β-oxo coordinated silver carbenoids were proposed as an intermediate based on the reaction profiles.
- Koo, Jaeyoung,Park, Hyun-Sub,Shin, Seunghoon
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supporting information
p. 834 - 839
(2013/02/25)
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- Investigation of the lipase-catalysed reaction of aliphatic amines with ethyl propiolate as a route to N-substituted propiolamides
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The lipase-catalysed reaction of aliphatic amine with ethyl propiolate was investigated using benzylamine as reference amine. The conditions were optimised to favour the 1,2-addition, i.e., formation of N-benzylprop-2-ynamide, versus the 1,4-addition. Immobilised Candida antarctica lipase (CALB) was found to be the most efficient enzyme, and the reactions were performed in solvents, such as tBME, dioxane or toluene. The methods were used to prepare propiolamides from aliphatic amines in good to excellent yields. The reactivity of O- and S-nucleophiles was compared in the same conditions.
- Bonte, Simon,Ghinea, Ioana Otilia,Baussanne, Isabelle,Xuereb, Jean-Paul,Dinica, Rodica,Demeunynck, Martine
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p. 5495 - 5500
(2013/07/05)
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- Highly efficient desilylation of 3-trimethylsilylprop-2-ynamides by the action of KF-Al2O3
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A highly effective procedure has been developed for desilylation of 3-trimethylsilylprop-2-ynamides in the presence of KF-Al2O 3 as catalyst. The corresponding terminal prop-2-ynamides were obtained in high yield in methanol at 25°C using 5 mol % of the catalyst (reaction time 20 min). Rise in temperature leads to the formation of Z,E-3-methoxyprop-2-enamides or 3,3-dimethoxypropanamides as a result of tandem desilylation-addition of methanol, depending on the conditions.
- Andreev,Safronova,Medvedeva
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experimental part
p. 1797 - 1801
(2012/03/10)
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- Microwave solvent free regioselective 1,3 dipolar cycloaddition in the synthesis of 1,4 substituted [1,2,3]-triazoles as amide bond isosteres
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(Chemical Equation Presented) 1,3 Dipolar cycloaddition of Fmoc-amino azides and acetylenic amides produces under solvent free irradiation a mixture of 1,4 or 1,5 substituted [1,2,3]-triazoles. The presence of copper (I) iodide, plays a central role on regioselectivity. Four Fmoc-amino azides characterized by different steric hindrance in side chains, and three different terminal alkynes, provided only the 1,4 substituted regioisomer under thermal microwave heating. Good yields, low consumption of organic solvents and short reaction times are the main aspects of our procedure. Reactions are compared to regioselective copper (I) catalysed solution synthesis performed at room temperature.
- Perissutti, Elisa,Frecentese, Francesco,Fiorino, Ferdinando,Severino, Beatrice,Cirillo, Donatella,Santagada, Vincenzo,Caliendo, Giuseppe
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p. 815 - 819
(2008/04/12)
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- Acetylenic amides. 1. Synthesis of N-substituted-2-propynamides
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The efficient synthesis of N-substituted-2-propynamides was accomplished by three methods; the reaction of amines with either the N-hydroxysuccinimide ester or mixed anhydride of propiolic acid, or by the interaction of lithiotrimethylsilylacetylene with
- Coppola,Damon
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p. 2003 - 2010
(2007/10/02)
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