- Efficient enhancement of fluorescence emission via TPE functionalized cationic pillar[5]arene-based host–guest recognition-mediated supramolecular self-assembly
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A tetraphenylethene (TPE) functionalized cationic pillar[5]arene (CWP5-TPE) was successfully synthesized, and the intramolecular rotation of the TPE motif was restricted via cationic pillar[5]arene-based host–guest recognition-mediated supramolecular self
- Sun, Jifu,Shao, Li,Zhou, Jiong,Hua, Bin,Zhang, Zhihua,Li, Qing,Yang, Jie
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- Synthesis and properties of poly(2-methoxy-5-propagyloxy-1, 4-phenylenevinylene)
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New PPV derivatives containing cross-linkable acetylene groups, poly(2-methoxy-5-propagyloxy-l,4-phenylenevinylene) (PMPPV) and its PPV copolymers were synthesized through the soluble precursor polymers. PMPPV film was higly cross-linked and lost its properties of a conjugated polymer at over 200 °C. The electrical conductivities of PMPPV films were measured by four probe method after FeCl3 doping. The undrawn and 10 times drawn PMPPV films showed thier electrical conductivities of 1.5 × 10-1 and 92 S/cm, respectively. Conjugation length of poly(PV-co-MPPV) was controlled by changing the PMPPV monomer feed ratio.
- Hwang, Do-Hoon,Yoon, Chong-Bok,Moon, Ki-Jeong,Shim, Hong-Ku
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- Pentavalent pillar[5]arene-based glycoclusters and their multivalent binding to pathogenic bacterial lectins
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Anti-adhesive glycoclusters offer potential as therapeutic alternatives to classical antibiotics in treating infections. Pillar[5]arenes functionalised with either five galactose or five fucose residues were readily prepared using CuAAC reactions and eval
- Galanos, Nicolas,Gillon, Emilie,Imberty, Anne,Matthews, Susan E.,Vidal, Sébastien
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- The synthesis of pillar[5]arene functionalized graphene as a fluorescent probe for paraquat in living cells and mice
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As complex organisms vary in vivo, it remains a challenging task to get fluorescence 'turn on' imaging for special targets. To address this task, we have adopted a new strategy of inducing pillararene based host-guest interactions onto biocompatible graphene. By means of fluorescence competition displacement, hydrazino-pillar[5]arene modified graphene has been synthesized and provided as a 'turn on' probe for paraquat through monitoring of the fluorescence signal both in living cells and mice.
- Mao, Xiaowei,Liu, Ting,Bi, Jiahai,Luo, Li,Tian, Demei,Li, Haibing
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- Acid/Base-Controllable FRET and Self-Assembling Systems Fabricated by Rhodamine B Functionalized Pillar[5]arene-Based Host-Guest Recognition Motifs
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A novel supramolecular F?ster resonance energy transfer (FRET) system was fabricated by utilizing rhodamine B (RB) functionalized pillar[5]arene (EtP5-RB) and cyano-modified boron dipyrromethene (BDP-CN) based on their host-guest recognition at 5.0 × 10s
- Sun, Jifu,Hua, Bin,Li, Qing,Zhou, Jiong,Yang, Jie
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- A non-symmetric pillar[5]arene-based selective anion receptor for fluoride
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A novel non-symmetric pillar[5]arene-based anion receptor containing multiple triazole anion-binding sites was designed and synthesized. It has high affinity and selectivity for the fluoride anion.
- Yu, Guocan,Zhang, Zibin,Han, Chengyou,Xue, Min,Zhou, Qizhong,Huang, Feihe
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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 0055-0056
(2021/08/28)
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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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- Enantioselective Palladium-Catalyzed Hydrophosphinylation of Allenes with Phosphine Oxides: Access to Chiral Allylic Phosphine Oxides
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A Pd-catalyzed hydrophosphinylation of alkyl and aryl-oxyallenes with phosphine oxides has been developed for the efficient and rapid construction of a family of chiral allylic phosphine oxides with a diverse range of functional groups. This methodology was further applied in the facile construction of chiral 2H-chromene and later stage functionalization of cholesterol.
- Wang, Jun,Yang, Zhiping
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supporting information
p. 27288 - 27292
(2021/11/17)
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- Synthesis of pterocarpans through palladium-catalyzed oxyarylation of alkoxy-2H-chromenes with o-iodophenols
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The oxyarylation of alkoxy-2H-chromenes (1a-e) with o-iodophenols substituted by electron-withdrawing (CHO) and electron-donating (OMe) groups is studied under two experimental conditions: a) Pd(OAc)2, Ag2CO3 in PEG-400 at 140 °C, 10 min and b) oxime-based palladacycle, DIPEA, in PEG-400 at 150 °C, 3–4 h. Pterocarpans are obtained in moderate to good chemical yields.
- Gaspar, Francisco V.,Barcellos, Julio C.F.,Cívicos, José F.,Merino, Pedro,Nájera, Carmen,Costa, Paulo R.R.
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- Synthesis of a new solvent-responsive pillar[5]arene-based [1]rotaxane molecular machine
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In this work, we designed a new pillar[5]arene-based molecular machine responsive to the polarity of different solvents, which can exist in an interlocked structure in CDCl3 and CD3OD, and can exist in an extended form in DMSO and was studied by 1H and 2D NMR spectroscopy, HR(MS) and fluorescence spectroscopy.
- Li, Runan,Lin, Po-Han,Meguellati, Kamel,Tian, Huasheng
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supporting information
p. 10628 - 10632
(2020/07/13)
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- Regiodivergent Hydration-Cyclization of Diynones under Gold Catalysis
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Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration-oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.
- Mu?oz, Miguel A.,Sanz, Roberto,Solas, Marta,Suárez-Pantiga, Samuel
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supporting information
p. 7681 - 7687
(2020/10/12)
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- Iron-Mediated Cyclization of 1,3-Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene-Fused Chromenes
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The synthesis of selenophene-fused chromene derivatives starting from 1,3-diynyl propargyl aryl ethers is reported herein. The method is based on carbon-carbon, carbon-selenium, selenium-carbon and carbon-selenium bonds formation in a one-pot protocol, using iron(III) chloride and dibutyl diselenide as promoters. The same reaction conditions were applied to propargyl anilines leading to the formation of 1-(butylselanyl)-selenophene quinolines. The results showed that the dilution and temperature of substrate addition had a crucial influence in the products obtained. When the substrates were added at room temperature, in the absence of a solvent, a mixture of products was obtained, whereas the slowly addition (15 min) of starting materials, as a dichloromethane solution, at 0 °C led to the product formation in good yields. The mechanistic study indicates that the cooperative action between iron(III) chloride and dibutyl diselenide was essential to promote the cyclization, whereas separately none of them was effective in promoting the cyclization. We proved the synthetic utility of heterocycles obtained in the Suzuki cross coupling reaction, giving the corresponding cross-coupled products in good yields. In addition, the organoselenium moiety was removed from the structures of products by using n-butyllithium. (Figure presented.).
- Back, Davi F.,Lutz, Guilherme,Zeni, Gilson
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p. 1096 - 1105
(2020/01/25)
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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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- Ethyl lactate as a renewable carbonyl source for the synthesis of diynones
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Ethyl lactate, a sustainable feedstock, serves as a highly attractive building block for the synthesis of value-added chemicals such as skipped diynones and, after gold-catalyzed transposition, conjugated diynones. Green solvents are involved in all steps
- Solas, Marta,Suárez-Pantiga, Samuel,Sanz, Roberto
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supporting information
p. 213 - 218
(2019/01/28)
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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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- Bimetal-Catalyzed Cascade Reaction for Efficient Synthesis of N-Isopropenyl 1,2,3-Triazoles via In-Situ Generated 2-Azidopropenes
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A bimetal-catalyzed cascade reaction for the synthesis of N-isopropenyl 1,2,3-triazoles in high yield is reported. This reaction involves the generation of 2-azidopropenes in situ by C(sp3)-OAr bond cleavage for click reaction and features a broad substrate scope, good functional group tolerance and readily available substrates.
- Liu, Zhenhua,Hao, Wenjing,Liu, Zhixian,Gao, Wen,Zhang, Zhihai,Zhang, Yanan,Li, Xiang,Tong, Lili,Tang, Bo
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supporting information
p. 2149 - 2154
(2019/06/13)
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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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- Discovery of cyclopropyl chromane-derived pyridopyrazine-1,6-dione γ-secretase modulators with robust central efficacy
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Herein we describe the discovery of a novel series of cyclopropyl chromane-derived pyridopyrazine-1,6-dione γ-secretase modulators for the treatment of Alzheimer's disease (AD). Using ligand-based design tactics such as conformational analysis and molecul
- Pettersson, Martin,Johnson, Douglas S.,Rankic, Danica A.,Kauffman, Gregory W.,Am Ende, Christopher W.,Butler, Todd W.,Boscoe, Brian,Evrard, Edelweiss,Helal, Christopher J.,Humphrey, John M.,Stepan, Antonia F.,Stiff, Cory M.,Yang, Eddie,Xie, Longfei,Bales, Kelly R.,Hajos-Korcsok, Eva,Jenkinson, Stephen,Pettersen, Betty,Pustilnik, Leslie R.,Ramirez, David S.,Steyn, Stefanus J.,Wood, Kathleen M.,Verhoest, Patrick R.
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supporting information
p. 730 - 743
(2017/04/27)
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- Discovery of efficient stimulators for adult hippocampal neurogenesis based on scaffolds in dragon's blood
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Reduction of hippocampal neurogenesis caused by aging and neurological disorders would impair neural circuits and result in memory loss. A new lead compound (N-trans-3′,4'-methylenedioxystilben-4-yl acetamide 27) has been discovered to efficiently stimulate adult rats' neurogenesis. In-depth structure-activity relationship studies proved the necessity of a stilbene scaffold that is absent in highly cytotoxic analogs such as chalcones and heteroaryl rings and inactive analogs such as diphenyl acetylene and diphenyl ethane, and validated the importance of an NH in the carboxamide and a methylenedioxy substituent on the benzene ring. Immunohistochemical staining and biochemical analysis indicate, in contrast to previously reported neuroprotective chemicals, N-stilbenyl carboxamides have extra capacity for neuroproliferation-type neurogenesis, thereby providing a foundation for improving the plasticity of the adult mammalian brain.
- Liang, Jian-Hua,Yang, Liang,Wu, Si,Liu, Si-Si,Cushman, Mark,Tian, Jing,Li, Nuo-Min,Yang, Qing-Hu,Zhang, He-Ao,Qiu, Yun-Jie,Xiang, Lin,Ma, Cong-Xuan,Li, Xue-Meng,Qing, Hong
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supporting information
p. 382 - 392
(2017/05/19)
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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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- 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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- 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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p. 10692 - 10704
(2016/12/16)
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- Synthesis of substituted 3-methylene-2,3-dihydrobenzofurans and 3-methylbenzofurans by rhodium (II)-catalyzed annulation
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Abstract The selective synthesis of substituted 3-methylene-2,3-dihydrobenzofurans and 3-methylbenzofurans has developed through Rh(II)-catalyzed denitrogenative annulation of N-sulfonyl-1,2,3-triazole at ambient to mild heating condition, respectively. F
- Chen, Ying-Yu,Chen, Kuan-Lin,Tyan, Yu-Chang,Liang, Chien-Fu,Lin, Po-Chiao
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p. 6210 - 6218
(2015/08/03)
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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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p. 126 - 139
(2015/03/03)
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- Calcium-catalyzed carboarylation of alkynes
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The first transition-metal-free carboarylation of alkynes with commercial and readily available alcohols as alkylating agents was realized in the presence of an environmentally benign calcium catalyst. Thereby, a novel protocol for the one-step synthesis of highly congested, all-carbon tetrasubstituted alkenes, as incorporated in potentially bioactive, complex dihydronaphthalene, chromene and dihydroquinoline structures, is provided. The reaction features an unprecedented, particularly wide substrate scope, good functional-group tolerance and simple experimental operation under mild reaction conditions. Finally free: The first transition-metal-free one-step synthesis of highly congested, all-carbon tetrasubstituted olefins has been realized by a calcium-catalyzed carboarylation reaction. Internal alkynes react with alcohols as alkylating reagent under mild reaction conditions, which provides access to a variety of useful structural scaffolds via highly reactive trisubstituted vinyl cations.
- Fu, Liang,Niggemann, Meike
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supporting information
p. 6367 - 6370
(2015/04/22)
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- Cu(I)-catalyzed efficient synthesis of 2'-triazolo-nucleoside conjugates
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A small library of thirty-two 2'-triazolyl uridine and 2'-triazolyl-5-methyluridine has been synthesized by Cu(I)-catalyzed condensation of 2'-azido-2'-deoxyuridine and 2'-azido-2'-deoxy-5-methyluridine with different alkynes and aryl propargyl ethers in almost quantitative yields. Triazolo-nucleoside conjugates, which can be evaluated for different biological activity for suitable drug development, were unambiguously identified on the basis of 1H NMR, 13C NMR, IR, and HRMS data analysis. These compounds have been synthesized for the first time and have not been reported in the literature earlier.
- Mathur,Rana,Olsen,Parmar,Prasad
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p. 701 - 710
(2015/05/13)
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- Design and synthesis of 2′-Deoxy-2′-[(1,2,3)Triazol-1-Yl]uridines using click chemistry approach
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A series of novel nucleosides bearing a 1,2,3-triazole moiety at the 2′-position of the sugar moiety has been synthesized starting from 2′-azidouridine and using the copper (I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction. The reactions proceeded in overall yield of 52-82% and gave almost exclusively the 1,4-disubstituted 1,2,3-triazoles. The 2′-azidouridine was synthesized from uridine in two steps, and reacted with a variety of differently substituted alkynes to give the desired 2′-triazole-substituted uridine derivatives.
- Kumar, Surender
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p. 371 - 378
(2015/05/05)
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- A click chemistry approach for the synthesis of mono and bis aryloxy linked coumarinyl triazoles as anti-tubercular agents
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A series of mono and bis-triazole coumarin hybrids 6aeu and 9aef respectively have been synthesized using 4-(azidomethyl)-2H-chromen-2-ones 5aei and aryl propargyl ethers 2aec/8 employing Click chemistry modified protocol for Azide-Alkyne cycloadditions(CuAAC). Anti-tubercular screening showed moderate activity for mono aryloxy compounds 6aeu with MIC 50-100 μg/mL, whereas the bis compounds 9aef were more effective with MICs between 0.2 and 12.5 μg/mL. Molecular modeling and 3DQSAR measurements using CoMFA and Topomer CoMFA further supported the observed results. The bis compound 9b showed excellent activity with MIC value as low as 0.2 μg/mL.
- Anand, Ashish,Naik, Reshma J.,Revankar, Hrishikesh M.,Kulkarni, Manohar V.,Dixit, Sheshagiri R.,Joshi, Shrinivas D.
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p. 194 - 207
(2015/11/03)
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- Indium-catalyzed intramolecular hydroarylation of aryl propargyl ethers
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Indium(iii) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with terminal and internal alkynes bearing electron-rich and electron-deficient substituents in the benzenes
- Alonso-Maran, Lorena,Martnez, M. Montserrat,Sarandeses, Luis A.,Sestelo, Jos Prez
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supporting information
p. 379 - 387
(2015/02/02)
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- Microwave-assisted synthesis of 3,5-disubstituted isoxazoles and evaluation of their anti-ageing activity
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One-pot uncatalysed microwave-assisted 1,3-dipolar cycloaddition reactions between in situ generated nitrile oxides and alkynes bearing protected antioxidant substituents, were regioselectively afforded 3,5-disubstituted isoxazoles. The yields were modera
- Koufaki, Maria,Fotopoulou, Theano,Kapetanou, Marianna,Heropoulos, Georgios A.,Gonos, Efstathios S.,Chondrogianni, Niki
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supporting information
p. 508 - 515
(2014/07/21)
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- Stimuli-responsive blue fluorescent supramolecular polymers based on a pillar[5]arene tetramer
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A tetraphenylethene-bridged pillarene tetramer with aggregation-induced emission properties forms an A4/B2-type supramolecular polymer and a gel with a symmetric neutral guest linker, showing a remarkable fluorescence emission enhancement in solution and the solid state and a good responsiveness to temperature and solvent composition. This journal is the Partner Organisations 2014.
- Song, Nan,Chen, Dai-Xiong,Qiu, Yu-Chen,Yang, Xiao-Yue,Xu, Bin,Tian, Wenjing,Yang, Ying-Wei
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supporting information
p. 8231 - 8234
(2014/07/21)
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- Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: Divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles
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The controllable synthesis of 3-methylene-2,3-dihydrobenzofurans 2 and 3-methylene-2,3-dihydroindoles 5 has been developed through Rh-catalyzed intramolecular annulation of aromatic rings with azavinyl carbenes. This journal is
- Tang, Xiang-Ying,Zhang, Yong-Sheng,He, Lv,Wei, Yin,Shi, Min
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supporting information
p. 133 - 136
(2015/01/09)
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- Asymmetric total synthesis of (-)-amphidinolide v through effective combinations of catalytic transformations
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An asymmetric total synthesis of (-)-amphidinolide V was accomplished. The synthesis features a base-catalyzed alkynyl silane alcoholysis/ring-closing enyne metathesis sequence for facile construction of a 1,3-diene motif. A diene RCM followed by a ring-c
- Volchkov, Ivan,Lee, Daesung
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supporting information
p. 5324 - 5327
(2013/06/04)
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- Anticancer (hexacarbonyldicobalt)propargyl aryl ethers: Synthesis, antiproliferative activity, apoptosis induction, and effect on cellular oxidative stress
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While an increasing number of (hexacarbonyldicobalt)alkynes have been found to possess antiproliferative activity against a number of cancer cell lines, the role of the organometallic moiety in this bioactivity is not well understood. To gain a better und
- Schimler, Sydonie D.,Hall, David J.,Debbert, Stefan L.
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- Strategies to reduce hERG K+ channel blockade. Exploring heteroaromaticity and rigidity in novel pyridine analogues of dofetilide
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Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG
- Carvalho, Jo?o F. S.,Louvel, Julien,Doornbos, Maarten L. J.,Klaasse, Elisabeth,Yu, Zhiyi,Brussee, Johannes,Ijzerman, Adriaan P.
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supporting information
p. 2828 - 2840
(2013/05/22)
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- Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers
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The two-step: Chroman-3-ones are important intermediates for organic synthesis and medicinal chemistry. However, their syntheses require multiple steps and are not efficient. By using gold-catalyzed alkyne oxidation, this versatile heterocycle can be prepared in only two steps from readily available phenols and with mostly high efficiencies (see scheme).
- Wang, Yanzhao,Ji, Kegong,Lan, Sylvester,Zhang, Liming
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supporting information; experimental part
p. 1915 - 1918
(2012/03/26)
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- Synthesis of 1,2,3-triazole-fused heterocycles via Pd-catalyzed cyclization of 5-iodotriazoles
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A convenient approach toward polycyclic frameworks containing fused 1,2,3-triazoles is described. The synthesis consists of a Cu-catalyzed cycloaddition and an intramolecular Pd-catalyzed direct arylation or Heck reaction, and affords the products in good to excellent yields.
- Schulman, Jacqueline M.,Friedman, Adam A.,Panteleev, Jane,Lautens, Mark
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supporting information; experimental part
p. 55 - 57
(2012/01/05)
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- Design, synthesis and biological evaluation of novel 2-methylpyrimidine-4- ylamine derivatives as inhibitors of Escherichia coli pyruvate dehydrogenase complex E1
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As potential inhibitors of Escherichia coli pyruvate dehydrogenase complex E1 (PDHc E1), a series of novel 2-methylpyrimidine-4-ylamine derivatives were designed based on the structure of the active site of PDHc E1 and synthesized using 'click chemistry'.
- He, Junbo,Feng, Lingling,Li, Jing,Tao, Ruijuan,Wang, Fang,Liao, Xun,Sun, Qiushuang,Long, Qingwu,Ren, Yanliang,Wan, Jian,He, Hongwu
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experimental part
p. 1665 - 1670
(2012/04/10)
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- Synthesis of a Heparan Sulfate Mimetic Library Targeting FGF and VEGF via Click Chemistry on a Monosaccharide Template
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A disulfated methyl 6-azido-6-deoxy-α-D-mannopyranoside template was used as a core structure for binding to the angiogenic growth factors FGF-1, FGF-2, and VEGF. The core structure was diversified in a rapid, parallel manner by employing the CuI-catalyzed Huisgen azide-alkyne cycloaddition ("click") reaction. The diversity was further extended by incorporating a Swern oxidation-Wittig reaction sequence on a click adduct of propargyl alcohol. Thus, the sulfated core was linked by various spacers to selected hydrophobic or polar motifs, which were designed to probe the protein surface surrounding the cationic heparan sulfate binding sites of the growth factors in order to improve affinity and selectivity. The affinities of the compounds for the growth factors were measured by surface plasmon resonance solution affinity assays. A lead compound was identified with micromolar binding affinity toward both FGF-1 and VEGF (Kd=84 and 49μM, respectively) and good selectivity over FGF-2 (29- and 51-fold, respectively).
- Liu, Ligong,Li, Caiping,Cochran, Siska,Jimmink, Shane,Ferro, Vito
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scheme or table
p. 1267 - 1275
(2012/08/08)
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- Hybrid system of metal/Bronsted acid relay catalysis for the intramolecular double hydroarylation and cationic cyclization of diyne diethers and diamines
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We have developed a hybrid system of metal/Bronsted acid relay catalysis for the intramolecular double hydroarylation and cationic cyclization of diyne diethers and diamines to give 4,4′-bi(2H-chromene), bi(2H-quinoline), and dioxafluoranthenes starting f
- Mo, Juntae,Eom, Dahan,Lee, Euichul,Lee, Phil Ho
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supporting information; experimental part
p. 3684 - 3687
(2012/08/28)
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- Semi-synthesis and biological evaluation of 1,2,3-triazole-based podophyllotoxin congeners as potent antitumor agents inducing apoptosis in HepG2 cells
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A series of 4β-[(4-substituted)-1,2,3-triazol-1-yl]podophyllotoxin congeners were synthesized by employing click chemistry and further evaluated for their antitumor activity by MTT assay. Among them, six congeners (10, 11, 12, 13, 22, and 24) exhibited ap
- Chen, Jinying,Ma, Liang,Zhang, Ronghong,Tang, Jie,Lai, Huijun,Wang, Jun,Wang, Guangcheng,Xu, Qinyuan,Chen, Tao,Peng, Fei,Qiu, Jingxiang,Liang, Xiaolin,Cao, Dong,Ran, Yan,Peng, Aihua,Wei, Yuquan,Chen, Lijuan
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p. 945 - 956
(2013/02/22)
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- TBAF-promoted elimination of vicinal dibromides having an adjacent O-functional group: Syntheses of 2-bromoalk-1-enes and alkynes
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Syntheses of 2-bromoalk-1-enes and alkynes were achieved in good yields by dehydrobromination of vicinal dibromides with tetrabutylammonium fluoride. Neighboring O-functional-group participation is important in determining elimination reactivity. Georg Thieme Verlag Stuttgart New York.
- Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
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experimental part
p. 2377 - 2382
(2011/09/16)
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- A regio- and diastereoselective platinum-catalyzed tandem [2+1]/[3+2] cycloaddition sequence
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Platinum complexes bearing phosphinous acids have efficiently promoted a tandem intermolecular sequence of [2+1]/[3+2] cycloaddition reactions. This process gave access to novel tricyclic systems and the cascade reactions were regio- and diastereoselective (see scheme; Cy=cyclohexyl). The [3+2] cycloaddition reaction was investigated further and two different alkyne partners were used. Copyright
- Achard, Thierry,Lepronier, Aymeric,Gimbert, Yves,Clavier, Herve,Giordano, Laurent,Tenaglia, Alphonse,Buono, Gerard
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supporting information; experimental part
p. 3552 - 3556
(2011/06/09)
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- An efficient synthesis of mono and bis-1,2,3-triazole AZT derivatives via copper(I)-catalyzed cycloaddition
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An efficient synthesis of novel mono and bis-1,2,3-triazoles 3'-azido-2'-deoxythymidine (AZT) derivatives via copper(I)-catalyzed 1,3-dipolar cycloaddition reaction is described. Starting from AZT and terminal alkyne derivatives, mono and bis-1,2,3-triazo
- Yuan, Jin-Wei,Qu, Ling-Bo,Chen, Xiao-Lan,Qu, Zhi-Bo,Liu, Xiang-Qian,Ke, Dian-Dian
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experimental part
p. 24 - 30
(2011/11/06)
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- Gold nanoparticles supported on TiO2 catalyse the cycloisomerisation/oxidative dimerisation of aryl propargyl ethers
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Gold nanoparticles supported on TiO2 (~1%) catalyse in high yields the selective cycloisomerisation of aryl propargyl ethers into the corresponding 2H-chromenes, under heterogeneous conditions. 2H,2′H-3, 3′-Bichromenes resulting from a catalytic oxidative dimerization pathway are also formed as by-products. The Royal Society of Chemistry 2011.
- Efe, Christina,Lykakis, Ioannis N.,Stratakis, Manolis
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supporting information; experimental part
p. 803 - 805
(2011/04/12)
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- Ph3PAuNTf2 as a superior catalyst for the selective synthesis of 2H-chromenes: Application to the concise synthesis of benzopyran natural products
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Ph3PAuNTf2 (≈1 mol-%) catalyzes the selective cycloisomerization of substituted aryl propargyl ethers into 2H-chromenes in excellent yields. Benzofuran byproducts are formed only in the case of electron-deficient arenes, in up to 7% relative yield. The Ph 3PAuNTf2-catalyzed cyclization of aryl propargyl ethers was applied as a key step to the concise synthesis of the naturally occurring benzopyrans seselin, xanthyletin, precocenes I and II, 8-(3′,3′- dimethylallyl)wenteria chromene, and 2,2-dimethyl-8-prenylchromene-6-propenoic acid. Ph3PAuNTf2 is a general, highly efficient, and product-selective catalyst for the clean synthesis of 2H-chromenes from the cycloisomerization of aryl propargyl ethers.The Ph3PAuNTf 2-catalyzed cyclization was applied as a key step in the synthesis of several benzopyran-bearing naturally occurring substances. Copyright
- Lykakis, Ioannis N.,Efe, Christina,Gryparis, Charis,Stratakis, Manolis
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supporting information; experimental part
p. 2334 - 2338
(2011/06/20)
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- TBAF-promoted dehydrobrominations of vicinal dibromides having an adjacent O-functional group
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Regioselective HBr elimination of vicinal dibromides having an adjacent oxygen functional group to give the corresponding 2-bromoalk-1-enes was controlled using 1.1 equivalents of TBAF. Two-step elimination to give the corresponding alkynes was controlled using 5.0 equivalents of TBAF. High yield and high selectivity require the presence of an oxygen functional group at the neighboring position of the elimination site.
- Kutsumura, Noriki,Kubokawa, Keisuke,Saito, Takao
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scheme or table
p. 2717 - 2720
(2010/12/25)
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- D-ring substituted 1,2,3-triazolyl 20-keto pregnenanes as potential anticancer agents: Synthesis and biological evaluation
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A facile synthesis of 21-triazolyl derivatives of pregnenolone and their potential antitumour activity is reported. The scheme involves the transformation of the starting pregnenolone acetate into pregnenolone, conversion of pregnenolone to 21-bromo pregnenolone and finally the one-pot, two-step in situ conversion of the bromo derivative to the 21-triazolyl pregnenolone using the 'click chemistry' approach. These derivatives were screened for their anticancer activity against seven human cancer cell lines. The compounds especially 5a, 5b, 5c, 5e, 5g and 5h exhibited significant anticancer activity with compound 5e as the most active in this study.
- Banday, Abid H.,Shameem, Shameem A.,Gupta,Kumar, H.M. Sampath
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experimental part
p. 801 - 804
(2010/10/01)
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- Site-selective and regioselective Diels-Alder reaction of allenyl aryl ethers
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The site-selectivity and regioselectivity of Diels-Alder reactions of allenyl aryl ethers with cyclopentadiene and acrolein were studied. While cyclopentadiene (as an electron-rich diene) only reacted with the external double bond of allenyl aryl ethers t
- Moghaddam, Firouz Matloubi,Kiamehr, Mostafa
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experimental part
p. 1333 - 1337
(2011/09/16)
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