- Prototropic rearrangement of 2-propynyl(methyl)amino, 2-propynyloxy, and 2-propynylsulfanyl derivatives of hetarenes under conditions of phase-transfer catalysis: Mechanism and limitations
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2-Propynyl derivatives of N-methylaniline, phenol, benzenethiol, 2-pyridinethiol, 2-pyrimidinethiol, and 1,3-benzoxazole-2-thiol were synthesized. Under conditions of phase-transfer catalysis, phenyl 2-propynyl sulfide is converted into allenyl phenyl sul
- Rubina,Fleisher,Abele,Popelis,Lukevits
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Read Online
- Uniform copper nanoparticles as an inexpensive and efficient catalyst for synthesis of novel β-carbonyl-1, 2, 3-triazoles in water medium
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Copper nanoparticles as an efficient, inexpensive catalyst were prepared via ball milling for synthesis of β-carbonyl 1, 2, 3-triazoles from azido alcohol by click reaction in water. An extensive range of raw materials such as sodium azide, phenacyl bromi
- Esmaeili-Shahri, Hadi,Eshghi, Hossein,Lari, Jalil,Rounaghi, Seyyed Amin,Esmaeili-Shahri, Effat
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- Defining the potential of aglycone modifications for affinity/selectivity enhancement against medically relevant lectins: Synthesis, activity screening, and HSQC-Based NMR Analysis
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The emerging significance of lectins for pathophysiological processes provides incentive for the design of potent inhibitors. To this end, systematic assessment of contributions to affinity and selectivity by distinct types of synthetic tailoring of glyco
- Rauthu, Subhash R.,Shiao, Tze Chieh,André, Sabine,Miller, Michelle C.,Madej, élodie,Mayo, Kevin H.,Gabius, Hans-Joachim,Roy, René
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- Synthesis, characterization and evaluation of optical band gap of new semiconductor polymers with N-aryl- 2,5-diphenyl-pyrrole units
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We used chemical modification to obtain new polymers that contain pyrrole units in the main chain, with electron-withdrawing groups acting as potential organic semiconductors, by means of chemical modification of the diacetylene-containing precursors. The
- Alexandrova, Larissa,Fomina, Lioudmila,Gavi?o, Ruben,Monroy, Olivia,Rumsh, Lev,Sánchez-Vergara, María-Elena,Salcedo, Roberto,Vázquez-Hernández, Giovanna Angélica,Zolotukhin, Mikhail G.
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- Affinity Enhancement of Protein Ligands by Reversible Covalent Modification of Neighboring Lysine Residues
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The discovery of protein ligands, capable of forming a reversible covalent bond with amino acid residues on a protein target of interest, may represent a general strategy for the discovery of potent small-molecule inhibitors. We analyzed the ability of di
- Dal Corso, Alberto,Catalano, Marco,Schmid, Anja,Scheuermann, J?rg,Neri, Dario
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- Benzenesulfonamides Incorporating Flexible Triazole Moieties Are Highly Effective Carbonic Anhydrase Inhibitors: Synthesis and Kinetic, Crystallographic, Computational, and Intraocular Pressure Lowering Investigations
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Herein we report the synthesis of two series of benzenesulfonamide containing compounds that incorporate the phenyl-1,2,3-triazole moieties. We explored the insertion of appropriate linkers, such as ether, thioether, and amino type, into the inner section
- Nocentini, Alessio,Ferraroni, Marta,Carta, Fabrizio,Ceruso, Mariangela,Gratteri, Paola,Lanzi, Cecilia,Masini, Emanuela,Supuran, Claudiu T.
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- Unusual absence of FRET in triazole bridged coumarin-hydroxyquinoline, an active sensor forHg2+detection
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A triazole-bridged coumarin conjugated quinoline sensor has been ‘click’-synthesized by Cu(i) catalyzed Huisgen cycloaddition, and it exhibited high selectivity for toxicHg2+. Surprisingly, no evidence of energy transfer from the quinoline moiety to coumarin has been found, substantiated by time-resolved fluorescence study. The possible binding mode of this sensor toHg2+has been establishedviaNMR study, steady-state and time-resolved fluorescence spectroscopy, which is further supported by TDDFT calculations. The sensor has been found to be cell membrane permeable and non-toxic, and hence is suitable for intracellularHg2+detection.
- Chatterjee, Soumit,Dey, Swapan,Hira, Sumit K.,Mondal, Surajit,Nayek, Hari Pada,Patra, Niladri
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- Design and synthesis of 1,2,3-triazole-etodolac hybrids as potent anticancer molecules
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A series of novel 1,2,3-triazole-etodolac hybrids (6a-l) were designed and synthesized as potent anti-cancer molecules. The synthesis strongly relied on Huisgen's 1,3-dipolar cycloaddition between etodolac azide 3 and substituted terminal alkynes 5a-l. Th
- Kummari, Bhaskar,Polkam, Naveen,Ramesh, Perla,Anantaraju, Hasithashilpa,Yogeeswari, Perumal,Anireddy, Jaya Shree,Guggilapu, Sravanthi Devi,Babu, Bathini Nagendra
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- Synthesis and application of a fluorescent ?turn-off? triazolyl-coumarin-based fluorescent chemosensor for the sensing of fe3+ ions in aqueous solutions
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Two coumarin derivatives containing triazole moieties have been synthesized using “click chemistry” protocol and investigated as chemosensors for the detection of metal ions. These compounds displayed a strong preference for Fe3+ ions with comp
- Mama, Neliswa,Battison, Aidan
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- Compound of dipyrrolopyridine structure Preparation method and medical application
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The invention discloses a compound with a dipyrrolo-pyridine structure as well as a preparation method and medical application thereof. The compound provided by the invention has obvious inhibitory activity on JAK family proteins, is an effective JAK inhibitor, and has the prospect of being developed into drugs for inhibiting JAK and further treating diseases.
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Paragraph 0163-0166
(2021/08/25)
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- Preparation method and application of propyne aryl ether compound
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The invention particularly relates to a method for preparing propyne aryl ether compounds from aryl phenol, halogenated propyne and derivatives of the halogenated propyne, and belongs to the technical field of preparation of the propyne aryl ether compoun
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Paragraph 0040-0042
(2021/08/28)
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- Strategic Design of Catalytic Lysine-Targeting Reversible Covalent BCR-ABL Inhibitors**
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Targeted covalent inhibitors have re-emerged as validated drugs to overcome acquired resistance in cancer treatment. Herein, by using a carbonyl boronic acid (CBA) warhead, we report the structure-based design of BCR-ABL inhibitors via reversible covalent targeting of the catalytic lysine with improved potency against both wild-type and mutant ABL kinases, especially ABLT315I bearing the gatekeeper residue mutation. We show the evolutionarily conserved lysine can be targeted selectively, and the selectivity depends largely on molecular recognition of the non-covalent pharmacophore in this class of inhibitors, probably due to the moderate reactivity of the warhead. We report the first co-crystal structures of covalent inhibitor-ABL kinase domain complexes, providing insights into the interaction of this warhead with the catalytic lysine. We also employed label-free mass spectrometry to evaluate off-targets of our compounds at proteome-wide level in different mammalian cells.
- Anantharajan, Jothi,Baburajendran, Nithya,Foo, Klement,Joy, Joma K.,Keller, Thomas H.,Kwek, Perlyn Z.,Li, Rong,Liu, Boping,Poulsen, Anders,Quach, David,Retna, Priya,Tang, Guanghui,Tee, Doris H. Y.,Wee, John L. K.,Yang, Wan-Qi,Yao, Shao Q.,Zhang, Chong-Jing
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supporting information
p. 17131 - 17137
(2021/06/28)
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- Synthesis of sorafenib analogues incorporating a 1,2,3-triazole ring and cytotoxicity towards hepatocellular carcinoma cell lines
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A series of 1,2,3-triazole-containing Sorafenib analogues, in which the aryl urea moiety of Sorafenib (1) was replaced with a 1,2,3-triazole ring linking a substituted phenoxy fragment, were prepared successfully via Huisgen 1,3-dipolar cycloaddition and
- Palakhachane, Sarinya,Ketkaew, Yuwaporn,Chuaypen, Natthaya,Sirirak, Jitnapa,Boonsombat, Jutatip,Ruchirawat, Somsak,Tangkijvanich, Pisit,Suksamrarn, Apichart,Limpachayaporn, Panupun
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supporting information
(2021/04/15)
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- Metal-Free Synthesis of Selenodihydronaphthalenes by Selenoxide-Mediated Electrophilic Cyclization of Alkynes
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A transition-metal-free, selenium mediated electrophilic cyclization reaction was realized through a one-pot procedure between simple alkynes and triflic anhydride-activated selenoxides to give selenium containing dihydronaphthalene products. This method gave good to very high yields for all products, including selenium-substituted phenanthrene, dihydroquinoline, 2H-chromene, and coumarin, which can be further transformed to other functionalized compounds.
- An, Shaoyu,Li, Pingfan,Zhang, Zhong
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p. 3059 - 3070
(2021/07/22)
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- N-ARYL SULFONAMIDE DERIVATIVES AS VACCINE ADJUVANT
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Bis-aryl sulfonamide compounds and methods of using those compounds, e.g., in a method of enhancing or prolonging an immune response, are provided. For example, the compounds may be employed with a vaccine and optionally at least one other adjuvant and/or one or more TLR ligands, at least one MAP kinase inhibitor, or any combination thereof.
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Page/Page column 101-102
(2021/02/26)
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- Glucosyl-1,2,3-triazoles derived from eugenol and analogues: Synthesis, anti-Candida activity, and molecular modeling studies in CYP-51
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This work describes the synthesis, anti-Candida, and molecular modeling studies of eighteen new glucosyl-1,2,3-triazoles derived from eugenol and correlated phenols. The new compounds were characterized by combined Fourier Transform Infrared, 1H and 13C nuclear magnetic resonance and spectroscopy of high-resolution mass spectrometry. The synthesized compounds did not show significant cytotoxicity against healthy fibroblast human cells (MCR-5) providing interesting selectivity indexes (SI) to active compounds. Considering the antifungal activity, nine compounds showed anti-Candida potential and the peracetylated triazoles 17 and 18 were the most promising ones. Eugenol derivative 17 was active against three species of Candida at 26.1–52.1?μM. This compound was four times more potent than fluconazole against Candida krusei and less toxic (SI?>?6.6) against the MCR-5 cells than fluconazole (SI?>?3.3) considering this strain. Dihydroeugenol derivative 18?showed similar activity to 17 and was four times more potent and less toxic than fluconazole against C.?krusei. The deacetylated glucosides and non-glucosylated corresponding derivatives did not show considerable antifungal action, suggesting that the acetyl groups are essential for their anti-Candida activity. Molecular docking coupled with molecular dynamics showed that 14α-lanosterol demethylase is a feasible molecular target, since 17 and 18 could bind to this enzyme once deacetylated in vivo, thereby acting as prodrugs. Also, these studies demonstrated the importance of hydrophobic substituents at the phenyl ring.
- Magalh?es, Lorena Severiano de,Reis, Adriana Cotta Cardoso,Nakao, Izadora Amaral,Péret, Vinícius Augusto Campos,Reis, Rúbia Castro Fernandes Melo,Silva, Naiara Chaves,Dias, Amanda Latércia Tranches,Carvalho, Diogo Teixeira,Dias, Danielle Ferreira,Brand?o, Geraldo Célio,Braga, Saulo Fehelberg Pinto,Souza, Thiago Belarmino de
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p. 903 - 913
(2021/09/15)
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- Access to Hydroxy-Functionalized Polypropylene through Coordination Polymerization
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Preparation of polyethylenes containing hydroxy groups has been already industrialized through radical copolymerization under harsh conditions followed by alcoholysis. By contrast, hydroxy-functionalized polypropylene has proven a rather challenging goal
- Cui, Dongmei,Douair, Iskander,Maron, Laurent,Wang, Tiantian,Wu, Chunji,Zhong, Yuanhao
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supporting information
p. 4947 - 4952
(2020/02/13)
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- Design, synthesis and biological activity of novel substituted 3-benzoic acid derivatives as MtDHFR inhibitors
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The enzyme dihydrofolate reductase from M. tuberculosis (MtDHFR) has a high unexploited potential to be a target for new drugs against tuberculosis (TB), due to its importance for pathogen survival. Preliminary studies have obtained fragment-like molecule
- Dias, Marcio Vinícius Bertacine,Ferreira, Glaucio Monteiro,Kronenberger, Thales,Parise-Filho, Roberto,Pavan, Fernando Rogério,Poso, Antti,Ribeiro, Jo?o Augusto,Tavares, Maurício Temotheo,Trossini, Gustavo Henrique Goulart,da Silva Santos, Soraya,de Souza, Alfredo Danilo Ferreira
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- Novel ferrocene-based 1,2,3-triazolyl compounds: Synthesis, anti-migration properties and catalytic effects on oxidizers during combustion
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To tackle high-migratory and high-volatility problem of marketed neutral ferrocene-based burning rate catalysts, twenty-one ferrocene-based 1,2,3-triazolyl compounds (Fc-TAZs) were synthesized by click reaction and characterized completely by NMR, FT-IR,
- Cheng, Wenqian,Shi, Xiaoling,Zhang, Yu,Jian, Yajun,Zhang, Guofang
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- Pyrazolopyrimidine compound serving as Btk inhibitor, as well as preparation method and application thereof (by machine translation)
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Field of the The present invention relates Btk to a pyrazolopyrimidine compound, a preparation method and an application. of the, compound, as well as (I) a preparation method and application of the compound, and specifically relates, to a, pharmaceutical composition, containing the above. compound or a pharmaceutical composition containing the above compound or a pharmaceutical composition containing the Btk compound, and an. application of the compound in the aspects of inhibition and the like. (by machine translation)
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Paragraph 0237; 0244-0247
(2020/01/25)
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- COMPOUNDS AND METHODS OF THEIR USE
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Provided are agents capable of binding the KIX domain of CBP or MED15 to inhibit the binding between SREBP1 and the KIX domain of MED15 or CBP. Also provided are compositions containing the agents and methods of their use.
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Page/Page column 84
(2020/05/19)
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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 0595-0600
(2020/05/02)
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- Gold(III)-Catalyzed Intermolecular Oxidation-Cyclization of Ynones: Access to 4-Substituted Chroman-3-ones
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A synthesis of 4-substituted chroman-3-one derivatives has been developed through a gold(III) catalyzed oxidation-cyclization of ynones in good to excellent yield using easily prepared substrates. A broad range of synthetically useful functional groups (halide, alkene, alkyne, phenolic hydroxyl) were tolerated. Further application of this method paves a new way to prepare the skeleton of oblarotenoids. A cascade oxidative cyclization for construction of pyrano[2,3-c]chromen-1(5H)-one derivatives is also presented. (Figure presented.).
- Li, Jian,Yang, Fang,Ma, Yang-Ting,Ji, Kegong
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supporting information
p. 2148 - 2153
(2019/03/28)
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- Method for synthesizing alkyne through catalytic asymmetric cross coupling (by machine translation)
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The invention belongs to the field of, asymmetric synthesis, and discloses a method for catalyzing asymmetric cross- coupling to synthesize: an alkyne, and the L method comprises, the following steps, of A: preparing B a cuprous, salt and C a: ligand; preparing a catalyst; adding a base; reacting the compound with the compound with the compound; and reacting the compound with the compound. Of these, one of them, X is selected from the group consisting of, R halogens. 1 Optionally substituted heteroarylsulfonylcyanamide groups selected from the, group consisting, of optionally substituted, phenyl groups In-flight vehicle, R6 Trialkyl silyl groups or alkyl radicals, R2 Cycloalkyl radicals optionally substituted with an, optionally substituted alkyl, (CH radical2 )n R4 Multi,layer chain, n=0-10,R saw blade4 A group selected, from, the group consisting of phenyl, alkenyl, aralkynyls, noonyloxy,and, noonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylsulphonylphenyl disiloxy-radicals. R3 A ligand, selected from hydrogen or any of the functional groups, is selected from the group consisting of, hydrogen and any L other functional group. The method, R disclosed by the, A invention has the, advantages of good catalytic, R ’ effect, wide application range. and high catalytic efficiency, and the, method disclosed by the, invention has the. advantages of good catalytic effect, wide application range and high catalytic efficiency. (by machine translation)
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Paragraph 0171; 0199-0201
(2020/01/12)
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- Pyrazolopyrimidine [3,4-d] compound as well as preparation method and application thereof
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The invention relates to a compound which is a Bruton tyrosine kinase inhibitor. In addition, the invention discloses a pharmaceutical ingredient and a preparation that comprise the compound, and an application of the kinase inhibitor. The compound can be used independently or combined with other compounds for treating kinase mediated or kinase-dependent symptoms.
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Paragraph 0230; 0232; 0233; 0234
(2019/06/10)
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- Iron(III)-Catalyzed Domino Claisen Rearrangement/Regio- And Chemoselective Aerobic Dehydrogenative Cyclization of β-Naphthyl-Substituted-Allenylmethyl Ether
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An FeCl3-catalyzed allenic Claisen rearrangement/regio- and chemoselective aerobic dehydrogenative cyclization domino reaction is developed, providing a wide range of 2-aryl/alkyl, 3-(substituted-vinyl)naphtho[2,1-b]furans in high yields at 95-130 °C in a
- Zhang, Chenyun,Zhen, Long,Yao, Zhi,Jiang, Liqin
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supporting information
p. 955 - 959
(2019/02/05)
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- Design, synthesis, structural characterization and in vitro evaluation of new 1,4-disubstituted-1,2,3-triazole derivatives against glioblastoma cells
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A new series of 1,4-disubstituted-1,2,3-triazole derivatives were synthesized through the copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition (Click chemistry) and their inhibitory activities were evaluated against different human glioblastoma (GBM) c
- da Silva, Veronica D.,de Faria, Bruna M.,Colombo, Eduardo,Ascari, Lucas,Freitas, Gabriella P.A.,Flores, Leon? S.,Cordeiro, Yraima,Rom?o, Luciana,Buarque, Camilla D.
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- Novel glucopyranoside C2-derived 1,2,3-triazoles displaying selective inhibition of O-GlcNAcase (OGA)
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O-GlcNAcylation or O-GlcNAc modification is a post-translational modification of several proteins responsible for fundamental cellular processes. Dysregulation of the O-GlcNAc pathway has been linked to the etiology of several diseases such as neurodegenerative and cardiovascular diseases, type 2 diabetes and cancer. O-GlcNAcase (OGA) catalyzes the removal of O-GlcNAc from the modified proteins and several carbohydrate-based OGA inhibitors have been synthesized to understand the role of O-GlcNAc-modified proteins in physiological and pathological conditions. However, many of the inhibitors lack selectivity for OGA over lysosomal hexosaminidases A and B. Aiming the selectively inhibition of OGA, we propose herein the synthesis of twelve novel glucopyranoside derivatives exploring the bioisosteric replacement of the GlcNAc 2-acetamide group by 1,4-disubstituted 1,2,3-triazole ring, bearing a variety of central chains with different shapes. Compounds were readily prepared through “Copper(I) Catalyzed Azide/Alkyne Cycloaddition” (CuAAC) reaction between a sugar azide and different terminal alkynes. Initial Western Blot analyses and further inhibitory assays proved that compounds 6a (IC50 = 0.50 ± 0.02 μM, OGA), 6k (IC50 = 0.52 ± 0.01 μM, OGA) and 6l (IC50 = 0.72 ± 0.02 μM, OGA) were the most potent and selective compounds of the series. Structure-activity relationship analyses and molecular docking simulations demonstrated that the bridge of two-carbon atoms between the C-4 position of the triazole and the phenyl ring (6a), which may be replaced by heteroatoms such as N (6k) or O (6l), is fundamental for accommodation and inhibition within OGA catalytic pocket.
- Igual, Michelle O.,Nunes, Paulo S.G.,da Costa, Rafael M.,Mantoani, Susimaire P.,Tostes, Rita C.,Carvalho, Ivone
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- 1,2,3-Triazole-based kojic acid analogs as potent tyrosinase inhibitors: Design, synthesis and biological evaluation
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A series of kojic acid-derived compounds 6a-p bearing aryloxymethyl-1H-1,2,3-triazol-1-yl moiety were designed by modifying primary alcoholic group of kojic acid as tyrosinase inhibitors. The target compounds 6a-p were synthesized via click reaction. All
- Ashooriha, Morteza,Khoshneviszadeh, Mehdi,Khoshneviszadeh, Mahsima,Moradi, Seyed Ershad,Rafiei, Alireza,Kardan, Mostafa,Emami, Saeed
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p. 414 - 422
(2018/11/21)
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- Preparation of novel 1,2,3-triazole furocoumarin derivatives via click chemistry and their anti-vitiligo activity
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The extracts of Psoralea corylifolia?L. were often used for the repigmentation of leukoderma (vitiligo) in traditional Uygur medicine thousands years ago. Nowadays, its active ingredient, furocoumarins, has been clinically applied since it exhibited stron
- Niu, Chao,Lu, Xueying,Aisa, Haji Akber
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p. 1671 - 1678
(2019/01/24)
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- Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors
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Structurally diverse trimethoxyphenyl-1,2,3-triazole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three cancer cell lines (PC3, MGC803 and HepG2). Among them, trimethoxyphenyl-1,2,3-triazole containing the
- Fu, Dong-Jun,Li, Ping,Wu, Bo-Wen,Cui, Xin-Xin,Zhao, Cheng-Bin,Zhang, Sai-Yang
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p. 309 - 322
(2019/01/30)
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- Synthesis of 3-Organoselenyl-2H-Coumarins from Propargylic Aryl Ethers via Oxidative Radical Cyclization
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A metal-free oxidative radical cyclization/selenylation of propargylic aryl ethers with diaryl diselenides was developed. This protocol provided an alternative method to synthesize 3-organoselenyl-2H-coumarins via the formation of C?Se bond, C?C bond, and C=O bond in one step. Moreover, a broad range of functional groups (such as halogen, aldehyde, ketone, cyano, and nitro group) were tolerated. (Figure presented.).
- Fang, Jun-Dan,Yan, Xiao-Biao,Zhou, Li,Wang, Yu-Zhao,Liu, Xue-Yuan
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supporting information
p. 1985 - 1990
(2019/03/13)
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- New: N -phenylacetamide-incorporated 1,2,3-triazoles: [Et3NH][OAc]-mediated efficient synthesis and biological evaluation
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A facile, highly efficient, and greener method for the synthesis of new 1,4-disubstituted-1,2,3-triazoles was conducted using [Et3NH][OAc] as a medium by the implementation of ultrasound irradiation via click chemistry, affording excellent yiel
- Akolkar, Satish V.,Nagargoje, Amol A.,Krishna, Vagolu S.,Sriram, Dharmarajan,Sangshetti, Jaiprakash N.,Damale, Manoj,Shingate, Bapurao B.
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p. 22080 - 22091
(2019/07/30)
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- Olefin hydroformylation and kinetic studies using mono- and trinuclear N,O-chelate rhodium(I)-aryl ether precatalysts
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Rh(I)-salicylaldimine-triazole mononuclear (6) and trinuclear (7) complexes based on an aryl-ether scaffold were investigated as precatalysts in the rhodium-catalysed hydroformylation of the terminal olefin, 1-octene, and internal olefins, 7-tetradecene and 4-octene. The complexes generally show good catalytic activity in the hydroformylation of 1-octene at temperatures ranging from 75 °C to 95 °C and syngas pressures of 20 to 40 bar. The precatalysts have excellent stability and could be reused several times using organic solvent nanofiltration under optimum conditions of 85 °C and 40 bar. Kinetic studies using catalyst precursor 6 were investigated by evaluating the effect of temperature, syngas total pressure and catalyst loading on the rate of hydroformylation. The activation energy for the hydroformylation of 1-octene was calculated to be 62 kJ mol?1 and the experimental rate constants were found to be in good agreement with the predicted rate data obtained using a modified fundamental mechanism-based rate model.
- Siangwata, Shepherd,Breckwoldt, Nicholas C.C.,Goosen, Neill J.,Smith, Gregory S.
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- Diphenyl-Diselenide-Mediated Domino Claisen-Type Rearrangement/Cyclization of Propargylic Aryl Ethers: Synthesis of Naphthofuran-2-carboxaldehyde Derivatives
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A diphenyl-diselenide-mediated Claisen-type rearrangement/cyclization of propargylic aryl ethers under metal-free conditions is developed, affording various naphthofuran-2-carboxaldehydes in moderate to excellent yield. The broad substrate scope and excel
- Fang, Jun-Dan,Yan, Xiao-Biao,Lin, Wu-Jie,Zhao, Yi-Chuan,Liu, Xue-Yuan
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supporting information
p. 7635 - 7638
(2019/10/14)
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- Novel triazole-tetrahydroisoquinoline hybrids as human aromatase inhibitors
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Novel thirteen triazole-tetrahydroisoquinoline derivatives (2a-m) were synthesized and evaluated for their aromatase inhibitory activities. Seven triazoles showed significant aromatase inhibitory activity (IC50 = 0.07–1.9 μM). Interestingly, th
- Chamduang, Chanamon,Pingaew, Ratchanok,Prachayasittikul, Veda,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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supporting information
(2019/10/16)
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- Structure-Activity Relationship Studies to Identify Affinity Probes in Bis-aryl Sulfonamides That Prolong Immune Stimuli
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Agents that safely induce, enhance, or sustain multiple innate immune signaling pathways could be developed as potent vaccine adjuvants or coadjuvants. Using high-throughput screens with cell-based nuclear factor κB (NF-κB) and interferon stimulating response element (ISRE) reporter assays, we identified a bis-aryl sulfonamide bearing compound 1 that demonstrated sustained NF-κB and ISRE activation after a primary stimulus with lipopolysaccharide or interferon-α, respectively. Here, we present systematic structure-activity relationship (SAR) studies on the two phenyl rings and amide nitrogen of the sulfonamide group of compound 1 focused toward identification of affinity probes. The murine vaccination studies showed that compounds 1 and 33 when used as coadjuvants with monophosphoryl lipid A (MPLA) showed significant enhancement in antigen ovalbumin-specific immunoglobulin responses compared to MPLA alone. SAR studies pointed to the sites on the scaffold that can tolerate the introduction of aryl azide, biotin, and fluorescent rhodamine substituents to obtain several affinity and photoaffinity probes which will be utilized in concert for future target identification and mechanism of action studies.
- Chan, Michael,Lao, Fitzgerald S.,Chu, Paul J.,Shpigelman, Jonathan,Yao, Shiyin,Nan, Jason,Sato-Kaneko, Fumi,Li, Vicky,Hayashi, Tomoko,Corr, Maripat,Carson, Dennis A.,Cottam, Howard B.,Shukla, Nikunj M.
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supporting information
p. 9521 - 9540
(2019/11/11)
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- Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes
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Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.
- Lasányi, Dániel,Tolnai, Gergely L.
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supporting information
p. 10057 - 10062
(2019/12/24)
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- Rotating Catalysts Are Superior: Suppressing Product Inhibition by Anchimeric Assistance in Four-Component Catalytic Machinery
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Three distinct four-component supramolecular nanorotors, prepared by varying the rotator's structure and keeping all other components constant, exhibit rotational frequencies that differ by almost 2 orders of magnitude. When the rotors were used as catalyst for two click reactions, the product yield correlated with the speed of the machine, e.g., 20% at 0.50 kHz, 44% at 20 kHz and 62% at 42 kHz. The kinetic effect on the product yield is attributed to the ability of the rotating catalysts to displace the product more efficiently from the active site at higher speed (anchimeric assistance). This mechanistic hypothesis was convincingly corroborated by a linear correlation between product yield and product liberation.
- Biswas, Pronay Kumar,Saha, Suchismita,Paululat, Thomas,Schmittel, Michael
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supporting information
p. 9038 - 9041
(2018/07/05)
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- Copper(II) schiff base complexes with catalyst property: Experimental, theoretical, thermodynamic and biological studies
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Two novel copper(II) Schiff base complexes were synthesized and characterized by various physico-chemical and spectroscopic methods, revealing a distorted square planar geometry around the copper atom. The analytical data confirmed the 1:1 metal to ligand
- Esmaielzadeh, Sheida,Zarenezhad, Elham
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p. 416 - 428
(2018/07/05)
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- Nano-dispersed platinum(0) in organically modified silicate matrices as sustainable catalysts for a regioselective hydrosilylation of alkenes and alkynes
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Nano-dispersed platinum(0) particles stabilized in a range of organically modified silicate (ORMOSIL) matrices are investigated as sustainable catalysts for the hydrosilylation of alkenes and alkynes. In this study, five different siloxane matrices including triethoxysilane (HTEOS), methyltriethoxysilane (MTES), ethyltriethoxysilane (ETES), triethoxyvinylsilane (TEVS) and propyltriethoxysilane (PTES) are investigated, and the distribution of the metal particles in these materials analyzed by transition electron microscopy (TEM). The particles appeared to be generally of a small size, with a diameter of ca. 2-5 nm in each of these catalysts, however the distribution is not equally uniform from one matrix to the other. HTEOS, MTES and ETES that respectively carry a hydrogen, a methyl and an ethyl group on the triethoxysilane moiety, displayed a more uniform distribution, while particles appeared to be more scattered in the remaining matrices. Catalysts with a uniform particles distribution produced higher and consistent yields, while those with poor particles distribution produced lower and almost random yields, suggesting that the uniformity in particle distribution, and by extension the nature of the siloxane matrix, are important for the catalytic properties of these materials. The scope of the reaction was broadened to a range of olefins, with a goal of investigating the tolerability of the reaction toward a number of reactive functional groups, resulting in the preparation of 28 compounds. This catalytic system also enabled the hydrosilylation of a limited number of alkynes under the optimized reaction conditions.
- Duke, Brett J.,Akeroyd, Evan N.,Bhatt, Shreeja V.,Onyeagusi, Chibueze I.,Bhatt, Shreya V.,Adolph, Brandy R.,Fotie, Jean
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p. 11782 - 11795
(2018/07/25)
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- Waste-minimised copper-catalysed azide-alkyne cycloaddition in Polarclean as a reusable and safe reaction medium
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Herein we report the first example of a generally useful organic reaction, namely the copper-catalysed azide-alkyne cycloaddition, performed in a Polarclean/water mixture as a reaction medium. The process is very efficient, affording in 24 out of the 26 tested cases the desired triazole in quantitative yields. Product isolation is also very convenient, since the triazoles either precipitate or form a separate liquid phase, without the need to perform chromatographic separations. Moreover, since the metal catalyst is retained in the Polarclean/water phase, the catalyst/reaction medium can be easily reused for consecutive reaction runs, without an apparent loss in efficiency. This methodology is associated with very limited waste production, as evidenced by calculated E-factors in the range 2.6-3.7.
- Luciani, Lorenzo,Goff, Emily,Lanari, Daniela,Santoro, Stefano,Vaccaro, Luigi
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supporting information
p. 183 - 187
(2018/01/17)
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- 1,4-Substituted Triazoles as Nonsteroidal Anti-Androgens for Prostate Cancer Treatment
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Prostate cancer (PC) is the fifth leading cause of cancer death in men, and the androgen receptor (AR) represents the primary target for PC treatment, even though the disease frequently progresses toward androgen-independent forms. Most of the commerciall
- Ferroni, Claudia,Pepe, Antonella,Kim, Yeong Sang,Lee, Sunmin,Guerrini, Andrea,Parenti, Marco Daniele,Tesei, Anna,Zamagni, Alice,Cortesi, Michela,Zaffaroni, Nadia,De Cesare, Michelandrea,Beretta, Giovanni Luca,Trepel, Jane B.,Malhotra, Sanjay V.,Varchi, Greta
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supporting information
p. 3082 - 3093
(2017/04/21)
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- Cu2O spheres as an efficient source of catalytic Cu(I) species for performing azide-alkyne click reactions
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We report herein the high yield synthesis of Cu2O spheres displaying well-defined shapes and monodisperse sizes that could be employed as the source of highly catalytic active Cu(I) species towards click reactions between several of alkynes and azides to produce a variety of 1,2,3-triazoles under ligand-free and ambient conditions (in an open reactor). The utilization of Cu2O spheres enabled superior performance as compared to a conventional protocol in which CuSO4is employed in combination with sodium ascorbate as the catalyst system. In addition, the compounds were obtained in synthetically useful yields, and seven of them have not been previously reported. We believe the results reported herein shed new insights into the optimization of activity and versatility of click reactions towards the synthesis of target molecules in environmentally friendly conditions.
- Rodrigues, Thenner S.,da Silva, Anderson G.M.,de Oliveira, Lucas C.,da Silva, Adalberto M.,Teixeira, Róbson R.,Camargo, Pedro H.C.
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supporting information
p. 590 - 595
(2017/01/16)
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- Benzamide compound containing 1,2,3-triazole structure and application of benzamide compound
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The invention relates to benzamide derivatives containing a 1,2,3-triazole structure shown in a general formula I as well as pharmaceutically acceptable salts, hydrates or prodrugs thereof and a preparation method thereof. Substituent groups X, Ar, R1 and
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Paragraph 0072; 0077; 0078
(2018/03/24)
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- Ruthenium(II)- and copper(I)-catalyzed synthesis of click-xylosides and assessment of their glycosaminoglycan priming activity
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Xylosides are small molecules that serve as primers of glycosaminoglycan biosynthesis. Xyloside mediated modulation of biological functions depends on the extent of priming activity and fine structures of primed GAG chains. In earlier studies, copper (Cu)
- Mencio, Caitlin P.,Garud, Dinesh R.,Doi, Yosuke,Bi, Yiling,Vankayalapati, Hariprasad,Koketsu, Mamoru,Kuberan, Balagurunathan
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p. 5027 - 5030
(2017/10/18)
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- Design, synthesis and pharmacological analysis of 5-[4′-(substituted-methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles
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In the present paper 5-[4′-({4-[(4-aryloxy)methyl]-1H-1,2,3-triazol-1-yl}methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles (5a–g) and [2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl-substituted-1-carbodithioates (11h–q) have been designed and synthesized. These compounds were subjected to docking (against AT1 receptor protein enzyme in complex with Lisinopril), in vitro angiotensin converting enzyme inhibition, anti-proliferative, anti-inflammatory screening (through egg albumin denaturation inhibition and red blood cell membrane stabilization assay) and finally anti-fungal activity analyses. Some of the compounds have shown significant pharmacological properties.
- Kamble, Atulkumar,Kamble, Ravindra,Dodamani, Suneel,Jalalpure, Sunil,Rasal, Vijaykumar,Kumbar, Mahadev,Joshi, Shrinivas,Dixit, Sheshagiri
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p. 444 - 457
(2017/04/13)
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- Pd-Catalyzed Hydroamination of Alkoxyallenes with Azole Heterocycles: Examples and Mechanistic Proposal
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Palladium-catalyzed regio- and enantioselective addition of azole heterocycles to alkoxyallenes was developed (up to 92% yields and up to 94% ee). DFT calculations suggest a new Pd(0)-driven mechanistic pathway proceeding through protonation of the Pd-coo
- Bernar, Ivan,Fiser, Béla,Blanco-Ania, Daniel,Gómez-Bengoa, Enrique,Rutjes, Floris P. J. T.
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supporting information
p. 4211 - 4214
(2017/08/23)
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- Synthesis of Tetrasubstituted α,β-Unsaturated Aldehydes via Radical 1,4-Aryl Migration/Trifluoromethylthiolation Cascade Reaction of Aryl Propynyl Ethers
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A one-pot synthesis of tetrasubstituted acrylaldehydes via difunctionalization of aryl propynyl ethers has been achieved, which involves a trifluoromethylthiolation process and a radical 1,4-aryl migration from oxygen to carbon. The reaction shows excellent conversion of aryl propynyl ethers into trifluoromethyl-containing α,β-unsaturated aldehydes through a radical pathway. (Figure presented.).
- Guo, Chun-Huan,Chen, Dao-Qian,Chen, Si,Liu, Xue-Yuan
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supporting information
p. 2901 - 2906
(2017/09/08)
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- 2 - (1 ', 2', 3 '- triazole - 4' - [...]) - 1, 3, 4, 6 - O - acetyl - D - glucose and its preparation method and application
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The core structure of 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose with an anti-colorectal carcinoma activity is that a 1,2,4-triazole derivative substitutes 2-site of 1,3,4,6-O- acetyl-D-glucose. The above compound has a good activity of inhibiting colorectal carcinoma cells, and can be used as an anti-colorectal carcinoma medicine. A synthesis method of the above compound comprises the following steps: 2-amino-D-glucose hydrochloride and an azidation reagent are used as raw materials to generate a 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate under an alkaline condition; 3-propargyl bromide and phenylcarbinol react under the action of sodium hydride to generate phenyl propargyl ether; and the 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate and phenyl propargyl ether undergo a click reaction in a solvent under the catalysis of monovalent copper to generate 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose.
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Paragraph 0023; 0031; 0032; 0034
(2017/10/25)
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- Design, synthesis and biological evaluation of LBM-A5 derivatives as potent P-glycoprotein-mediated multidrug resistance inhibitors
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A novel series of P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) inhibitors with triazol-N-phenethyl-tetrahydroisoquinoline or triazol-N-ethyl-tetrahydroisoquinoline scaffold were designed and synthesized via click chemistry. Most of the synthesized compounds showed higher reversal activity than verapamil (VRP). Among them, the most potent compound 4 showed a comparable activity with the known potent P-gp inhibitor WK-X-34 with lower cytotoxicity toward K562 cells (IC50 >100 μM). Compared with VRP, compound 4 exhibited more potency in increasing drug accumulation in K562/A02 MDR cells. Moreover, compound 4 could significantly reverse MDR in a dose-dependent manner and also persist longer chemo-sensitizing effect than VRP with reversibility. Further mechanism studies revealed that compound 4 could remarkably increase the intracellular accumulation of Adriamycin (ADM) in K562/A02 cells as well as inhibit rhodamine-123 (Rh123) efflux from the cells. These results suggested that compound 4 may represent a promising candidate for developing P-gp-mediated MDR inhibitors.
- Wu, Yuxiang,Pan, Miaobo,Dai, Yuxuan,Liu, Baomin,Cui, Jian,Shi, Wei,Qiu, Qianqian,Huang, Wenlong,Qian, Hai
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p. 2287 - 2297
(2016/04/26)
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- Electrochemical assessment of phenol and triazoles derived from phenol (BPT) on API 5L X52 steel immersed in 1 M HCl
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The corrosion inhibition of phenol triazoles was tested with several halogens by means of electrochemical impedance and potentiodynamic polarization. We observed the importance of the 1,2,3-triazole ring in the chemical structure because significant inhibition efficiencies (η) > 90% were achieved at low concentrations with the different halogens. These compounds have a physisorption-type adsorption process, in accordance with the Langmuir model. For long immersion times, the organic inhibitor BPTI showed good corrosion protection during 504 hours of immersion with η > 80%. Furthermore, the hydrodynamic conditions proved that organic molecules experience a desorption process related to the different rotation velocities employed. Finally, it was demonstrated by SEM that the corrosion velocity is diminished when using the BPTI inhibitor at 50 ppm.
- Espinoza-Vázquez,Rodríguez-Gómez,González-Olvera,Angeles-Beltrán,Mendoza-Espinosa,Negrón-Silva
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p. 72885 - 72896
(2016/08/24)
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