86520-52-7Relevant articles and documents
Sequential synthesis of a new analogue of amlodipine bearing a short amino polyethyleneglycol chain
Legeay, Jean Christophe,Vanden Eynde, Jean Jacques,Bazureau, Jean Pierre
, p. 12081 - 12086 (2007)
3-Ethyl 5-methyl 2-[(2-(2-(2-aminoethoxy)ethoxy)ethoxy)methyl]-4-(2-chlorophenyl)-6-methy l-1,4-dihydropyridine-3,5-dicarboxylate as new analogue of amlodipine was prepared in five steps with an overall yield of 22%. The 1,4-dihydropyridine nucleus was built in two steps via Knoevenagel reaction and the amino group of this analogue has been prepared in good yield by Staudinger reduction of the azido 1,4-dihydropyridine precursor in the last step.
Alkanethiol containing glycopolymers: A tool for the detection of lectin binding
Huang, Mingchuan,Shen, Zhihong,Zhang, Yalong,Zeng, Xiangqun,Wang, Peng George
, p. 5379 - 5383 (2007)
Glycopolymers are useful macromolecules with a non-carbohydrate backbone for presenting saccharides in multivalent form. Here, glycopolymers containing mannose and alkanethiol linker were synthesized through substituting preactivated poly [N-(acryloyloxy) succinimide] (pNAS) with amine-containing monomer. With the obtained glycopolymers, a glycosurface was generated on the gold surface of quartz crystal microbalance (QCM) through self-assembled strategy by the use of alkanethiol functional group. Furthermore, the resulting glycosurface was used to detect the binding of mannose specific lectin concanavalin A (Con A).
Pentavalent Sialic Acid Conjugates Block Coxsackievirus A24 Variant and Human Adenovirus Type 37-Viruses That Cause Highly Contagious Eye Infections
Johansson, Emil,Caraballo, Rémi,Mistry, Nitesh,Zocher, Georg,Qian, Weixing,Andersson, C. David,Hurdiss, Daniel L.,Chandra, Naresh,Thompson, Rebecca,Fr?ngsmyr, Lars,Stehle, Thilo,Arnberg, Niklas,Elofsson, Mikael
, p. 2683 - 2691 (2020)
Coxsackievirus A24 variant (CVA24v) and human adenovirus 37 (HAdV-37) are leading causative agents of the severe and highly contagious ocular infections acute hemorrhagic conjunctivitis and epidemic keratoconjunctivitis, respectively. Currently, neither vaccines nor antiviral agents are available for treating these diseases, which affect millions of individuals worldwide. CVA24v and HAdV-37 utilize sialic acid as attachment receptors facilitating entry into host cells. Previously, we and others have shown that derivatives based on sialic acid are effective in preventing HAdV-37 binding and infection of cells. Here, we designed and synthesized novel pentavalent sialic acid conjugates and studied their inhibitory effect against CVA24v and HAdV-37 binding and infection of human corneal epithelial cells. The pentavalent conjugates are the first reported inhibitors of CVA24v infection and proved efficient in blocking HAdV-37 binding. Taken together, the pentavalent conjugates presented here form a basis for the development of general inhibitors of these highly contagious ocular pathogens.
A facile "click" reaction to fabricate a FRET-based ratiometric fluorescent Cu2+ probe
Hu, Zhangjun,Hu, Jiwen,Cui, Yang,Wang, Guannan,Zhang, Xuanjun,Uvdal, Kajsa,Gao, Hong-Wen
, p. 4467 - 4472 (2014)
A facile one-step Cu(i)-catalyzed "click" reaction, between a dansyl-azide and a propargyl-substituted rhodamine B hydrazide, is employed to fabricate a novel FRET ratiometric "off-on" fluorescent probe. The sensitive emission of the donor, a dansyl group, overlaps perfectly with the absorption of the acceptor, xanthene in the open-ring rhodamine. The proposed probe shows high selectivity towards Cu2+. The ratio of emission intensities at 568 and 540 nm (I568/I540) exhibits a drastic 28-fold enhancement upon addition of Cu2+. The probe shows an excellent linear relationship between emission ratios and the concentrations of Cu2+ from 10 to 50 μM, with a detection limit (S/N = 3) of 0.12 μM. The preliminary cellular studies demonstrated that the probe is cell membrane permeable and could be applied for ratiometric fluorescence imaging of intracellular Cu2+ with almost no cytotoxicity. The ingenuity of the probe design is to construct a FRET donor-acceptor interconnector and a selective receptor simultaneously by "click" reaction. The strategy was verified to have great potential for developing novel FRET probes for Cu2+. This journal is the Partner Organisations 2014.
Click chemistry oligomerisation of azido-alkyne-functionalised galactose accesses triazole-linked linear oligomers and macrocycles that inhibit Trypanosoma cruzi macrophage invasion
Campo, Vanessa L.,Ivanova, Irina M.,Carvalho, Ivone,Lopes, Carla D.,Carneiro, Zumira A.,Saalbach, Gerhard,Schenkman, Sergio,Da Silva, Jo?o Santana,Nepogodiev, Sergey A.,Field, Robert A.
, p. 7334 - 7353 (2015)
Abstract Reaction of 2-(2-(2-azidoethoxy)ethoxy)ethyl 6-O-(prop-2-ynyl)-β-d-galactopyranoside (7) under CuAAC conditions gives rise to mixed cyclic and linear triazole-linked oligomers, with individual compounds up to d.p. 5 isolable, along with mixed larger oligomers. The linear compounds resolve en bloc from the cyclic materials by RP HPLC, but are separable by gel permeation chromatography. The triazole-linked oligomers - pseudo-galactooligomers - were demonstrated to be acceptor substrates for the multi-copy cell surface trans-sialidase of the human parasite Trypanosoma cruzi. In addition, these multivalent TcTS ligands were able to block macrophage invasion by T. cruzi.
Virus-glycopolymer conjugates by copper(I) catalysis of atom transfer radical polymerization and azide-alkyne cycloadditiont
Gupta, Sayam Sen,Raja, Krishnaswami S.,Kaltgrad, Eiton,Strahle, Erica,Finn
, p. 4315 - 4317 (2005)
The CuI-catalyzed ATRP and azide-alkyne cycloaddition reactions together provide a versatile method for the synthesis of end-functionalized glycopolymers and their attachment to a suitably modified viral protein scaffold. The Royal Society of Chemistry 2005.
Hybrid triazolium and ammonium ions-contained hyperbranched polymer with enhanced ionic conductivity
Li, Hongfei,Wang, Cuifang,Liao, Xiaojuan,Xie, Meiran,Sun, Ruyi
, p. 297 - 305 (2017)
Hyperbranched poly(triazole) with tertiary amine moiety and longer flexible polyethylene glycol (PEG) terminal group (hb-PTA-PEG) was synthesized by successive Cu(I)-catalyzed azide-alkyne cycloaddition polymerization, and the corresponding hyperbranched poly(triazolium)s containing hybrid quaternary ammonium ion, [hb-PTA-PEG]+[I]? and [hb-PTA-PEG]+[TFSI]?, were obtained after N-alkylation and anion exchange reactions. These hyperbranched polymers presented broad electrochemical stability window of above 6.0 V versus Ag+/Ag and 5.3 V versus Li+/Li, and displayed low glass transition temperature in the range of ?13 to ?37 °C, owing to the hyperbranched structure combined with the hybrid ionic moiety and longer flexible PEG end-group. The ionic [hb-PTA-PEG]+[TFSI]? showed superior ionic conductivity, which was above 10?5 S cm?1 at 30 °C.
Aza-BODIPY probe for selective visualization of cyclooxygenase-2 in cancer cells
Pewklang, Thitima,Chansaenpak, Kantapat,Lai, Rung-Yi,Noisa, Parinya,Kamkaew, Anyanee
, p. 13372 - 13377 (2019)
AZB-IMC2 was developed as a COX-2 specific probe that exhibited a brighter fluorescence signal in cancer cells that overexpress COX-2 compared to normal cells. Oxidative stress agent-treated inflamed cell lines inducing high COX-2 levels revealed an enhanced fluorescence signal. Inhibitory studies showed a markedly reduced fluorescence intensity in cancer cells. The results suggested that AZB-IMC2 could be developed as a promising molecular tool for imaging guiding during surgery.
Development of a microfluidic "click chip" incorporating an immobilized Cu(i) catalyst
Li, Hairong,Whittenberg, Joseph J.,Zhou, Haiying,Ranganathan, David,Desai, Amit V.,Koziol, Jan,Zeng, Dexing,Kenis, Paul J. A.,Reichert, David E.
, p. 6142 - 6150 (2015)
We have developed a microfluidic "click chip" incorporating an immobilized Cu(i) catalyst for click reactions. The microfluidic device was fabricated from polydimethylsiloxane (PDMS) bonded to glass and featured ～14400 posts on the surface to improve catalyst immobilization. This design increased the immobilization efficiency and reduces the reagents' diffusion time to an active catalyst site. The device also incorporates five reservoirs to increase the reaction volume with minimal hydrodynamic pressure drop across the device. A novel water-soluble Tris-(benzyltriazolylmethyl)amine (TBTA) derivative capable of stabilizing Cu(i), ligand 2, was synthesized and successfully immobilized on the chip surface. The catalyst immobilized chip surface was characterized by X-ray photoelectron spectroscopy (XPS). The immobilization efficiency was evaluated via radiotracer methods: the immobilized Cu(i) was measured as 1136 ± 272 nmol and the surface immobilized Cu(i) density was 81 ± 20 nmol cm-2. The active Cu(i)-ligand 2 could be regenerated up to five times without losing any catalyst efficiency. The "click" reaction of Flu568-azide and propargylamine was studied on chip for proof-of-principle. The on-chip reaction yields were ca. 82% with a 50 min reaction time or ca. 55% with a 15 min period at 37 °C, which was higher than those obtained in the conventional reaction. The on-chip "click" reaction involving a biomolecule, cyclo(RGDfK) peptide was also studied and demonstrated a conversion yield of ca. 98%. These encouraging results show promise on the application of the Cu(i) catalyst immobilized "click chip" for the development of biomolecule based imaging agents. This journal is
Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions
Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter
supporting information, p. 133 - 146 (2021/11/04)
Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.
