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Mao Yamagami, Hiroshi Kamitakahara, Arata Yoshinaga, Toshiyuki Takano
This paper describes the design and synthesis of new trehalose-type diblock methylcellulose analogues with nonionic, cationic, and anionic cellobiosyl segments, namely 1-(tri-O-methyl-cellulosyl)-4-[β-d-glucopyranosyl-(1→4)-β-d-glucopyranosyloxymethyl]-1H-1,2,3-triazole (1), 1-(tri-O-methyl-cellulosyl)-4-[(6-amino-6-deoxy-β-d-glucopyranosyl)-(1→4)- 6-amino-6-deoxy-β-d-glucopyranosyloxymethyl]-1H-1,2,3-triazole (2), and 4-(tri-O-methyl-cellulosyloxymethyl)-1-[β-d-glucopyranuronosyl-(1→4)-β-d-glucopyranuronosyl]-1H-1,2,3-triazole (3), respectively...
March 1, 2018: Carbohydrate Polymers
Dino Berthold, Bernhard Breit
The rhodium-catalyzed asymmetric N1-selective and regioselective coupling of triazole derivatives with internal alkynes and terminal allenes gives access to secondary and tertiary allylic triazoles in very good enantioselectivities. For this process, three new members of the JosPOphos ligand family have been prepared and employed in catalysis. The optimized reaction conditions enable the coupling of triazoles with internal alkynes as well as with allenes, displaying a high tolerance for functional groups. A gram scale reaction provided N1-allyltriazole, which was subjected to various transformations highlighting synthetic utility...
January 19, 2018: Organic Letters
Priscila López-Rojas, Monika Janeczko, Konrad Kubiński, Ángel Amesty, Maciej Masłyk, Ana Estévez-Braun
A new series of coumarin-1,2,3-triazole conjugates with varied alkyl, phenyl and heterocycle moieties at C-4 of the triazole nucleus were synthesized using a copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated coumarin (3) or N-propargylated coumarin (6) with alkyl or aryl azides. Based on their minimal inhibitory concentrations (MICs) against selected microorganisms, six out of twenty-six compounds showed significant antibacterial activity towards Enterococcus faecalis (MIC = 12...
January 18, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Yu-Jie Wang, Yang-Yang Zhou, Hong-Guo Hao, Man Song, Na Zhang, Shuang Yao, Jing-Hui Yan, Zhi-Ming Zhang, Tong-Bu Lu
Two robust metal-organic frameworks (MOFs), {H4[Ni(π-H2O)2]2[Ni(rt-H2O)2]8Ni4(Tri)24}[VIVW12O40]2·24H2O (1) and {H[Ni(π-O)2]2[Ni(rt-H2O)2]8Ni4(Tri)24}[VIVW10VV2O40V2][VIVW9VV3O40VIV2]·24H2O (2) (Tri = 1,2,4-triazole), composed of polyoxometalates (POMs) and metal-organic units, were designed and synthesized by a hydrothermal method. Structure analysis indicates that there is a metal-organic crown [{Ni3(Tri)6(H2O)4}4] ({Ni12}) in these two compounds. In 1, the {Ni12} crown embraces four pendant Tri ligands that could capture a cationic [Ni(H2O)2]2+ group, resulting in the Ni13-Tri building unit [Ni(H2O)2{Ni3(Tri)6(H2O)4}4] ({Ni13})...
January 18, 2018: Inorganic Chemistry
Zhan Shi, Lingkun Meng, Ziyuan Niu, Chen Liang, XingLong Dong, Kang Liu, Guanghua Li, Chunguang Li, Yu Han, Shouhua Feng
A Cu MOF [Cu4(PMTD)2(H2O)3]·20H2O, 1, (Where PMTD is (1,4-phenylenebis(5-methyl-4H-1,2,4-triazole-3,4-diyl)bis(5-carboxylato-3,1-phenylene)bis(hydroperoxymethanide) with rare chiral Oh type of cage and dual functionalities of open metal sites and Lewis basic sites based on a designed U-shaped ligand was synthesized by hydrothermal method. It exhibits high-capacity of CO2, C2 and C3 hydrocarbon storage capacity under atmospheric pressure as well as high H2 (1.96% wt) adsorption capacity at 77K. Methane purification capacity was tested and verified step by step...
January 18, 2018: Chemistry: a European Journal
Ethan R Stewart, Matthew L Eldridge, Ian McHardy, Stuart H Cohen, George R Thompson
Coccidioidal meningitis remains a difficult clinical problem, and despite life-long therapy with triazole antifungals, relapses of disease and medication intolerance occur necessitating salvage treatment. We report two patients with recurrent coccidioidal meningitis who improved following a 2-week course of liposomal amphotericin B monotherapy and discuss potential advantages of this treatment option.
January 16, 2018: Mycopathologia
Yandong Dou, Xiaoxu Gu, Shasha Ying, Shen Zhu, Shian Yu, Wei Shen, Qing Zhu
A fluorogenic probe based on the novel fluorophore 5-triazole-quinoline was developed for the detection of hydrogen sulfide, an endogenous signaling molecule associated with the development of various diseases. The lysosome-targeted probe Lyso-HS was synthesized via C-H direct azidation from 8-aminoquinoline; it was able to detect H2S in 1 min and exhibited excellent turn-on ability with 95-fold fluorescence enhancement based on a new fluorochrome. The high quenching efficiency was further verified using time-dependent density functional theory (TDDFT)...
January 17, 2018: Organic & Biomolecular Chemistry
Benjamin MacCormick, Thu V Vuong, Emma R Master
A chemo-enzymatic pathway was developed to transform 4-O-methylglucuronic acid (MeGlcpA) containing xylo-oligosaccharides from beechwood into clickable monomers capable of polymerizing at room temperature and in aqueous conditions to form unique polytriazoles. While the gluco-oligosaccharide oxidase (GOOX) from Sarocladium strictum was used to oxidize C6-propargylated oligosaccharides, the acid-amine coupling reagents EDAC and DMT-MM were employed and compared for their ability to append click functionalities to carboxylic acid groups of enzyme-treated oligosaccharides...
January 17, 2018: Biomacromolecules
Rintaro Iwata Hara, Yuta Mitsuhashi, Keita Saito, Yuske Maeda, Takeshi Wada
Peptides are still difficult to synthesize when they contain sterically hindered amino acids such as α,α-di-substituted amino acids and N-substituted amino acids. In this study, solid-phase syntheses of oligopeptides containing multiple α-aminoisobutyric acid (Aib) residues were performed in high yields by using a non-swellable resin as the solid-support and 3-nitro-1,2,4-triazol-1-yl-tris(pyrrolidin-1-yl)phosphonium hexafluorophosphate (PyNTP) as the condensing reagent.
January 17, 2018: ACS Combinatorial Science
Michał Gładysz, Piotr Ruszkowski, Jan Milecki
We describe synthesis of novel acyclic nucleoside analogues which are building blocks for CuAAC reaction and their activity against two types of human cancer cell lines (HeLa, KB). Three of chosen compounds show promising cytotoxic activity. Synthesis pathway starting from simple and easily accessible substrates employing DMT or TBDPS protective groups is described. Adenosine and thymidine analogues containing alkyne moiety and adenosine analogue containing azido group were synthesized. The obtained units showed ability of forming triazole motif under the CuAAC reaction conditions...
January 16, 2018: Nucleosides, Nucleotides & Nucleic Acids
Victoria A Pollard, Samantha A Orr, Ross McLellan, Alan R Kennedy, Eva Hevia, Robert E Mulvey
Cooperativity between the Li and Al centres is implicated in catalytic hydroboration reactions of aldehydes and ketones with pinacolborane via heteroleptic lithium diamidodihydridoaluminates. In addition to implementing hydroalumination, these versatile heteroleptic ates can also perform as amido bases as illustrated with an acidic triazole.
January 16, 2018: Chemical Communications: Chem Comm
Burhan Khan, Abdul Hameed, Aaliya Minhaz, Muhammad Raza Shah
In the present study, we are reporting the synthesis of a triazoles incorporated fluorescent hexahydroquinoline appended calix[4]arene 7 and its highly selective optical recognition ability towards Hg2+. The optical sensor 7 was synthesized via two different synthetic pathways and unambiguously characterized by mass spectrometry and NMR spectroscopy. The stoichiometric ratio between 7 and Hg2+ was determined as 1:1 based on Job's plot and ESI-MS analysis. The chemosensor 7 selectively recognized Hg2+ in the presence of competitive cations such as Cu2+, Cu1+, Co3+, Ni2+, Ag1+, Fe2+, Fe3+, Cr3+, Pb2+, Cd2+, Zn2+, Sn2+, Ti4+, Sb3+, In3+, Ba2+, Ca2+, and K1+...
January 10, 2018: Journal of Hazardous Materials
Nidhi Gupta, Arem Qayum, Arun Raina, Ravi Shankar, Sumeet Gairola, Shashank Singh, Payare L Sangwan
A library of 28 analogs of bavachinin including aliphatic and aromatic ethers, epoxide, chalcone, oxime, semicarbazide, oxime ether and triazole derivatives have been synthesized and evaluated for cytotoxicity against four different human cancer cell lines. Bio-evaluation studies exhibited better cytotoxic profile for many analogs compare to bavachinin. Best results were observed for a 1,2,3-triazole analog (17i) with IC50 values 7.72, 16.08, 7.13 and 11.67 μM against lung (A549), prostate (PC-3), colon (HCT-116) and breast (MCF-7) cancer cell lines respectively...
January 8, 2018: European Journal of Medicinal Chemistry
Muhammad Saleem, Muhammad Rafiq, Yeon Ki Jeong, Dae Won Cho, Chong-Hyeak Kim, Sung-Yum Seo, Chang-Shik Choi, Seong-Karp Hong, Ki-Hwan Lee
BACKGROUND: In the past few decades, the design, synthesis and characterization of novel heterocyclic compounds with auspicious biological profile received the considerable attention of scientific community. Among them, the small and simple organic molecular backbone like triazole moiety have broad spectrum of applications in the medicinal as well as diagnostic areas. OBJECTIVE: The objective of present study was the synthesis, characterization and exploration of biological profile of 4-(2-fluorophenyl)-3-(3-methoxybenzyl)-1H-1,2,4-triazol-5(4H)-one (5)...
January 12, 2018: Medicinal Chemistry
Ruilin Zhang, Hongfei Gao, Yanming Ren, Yulong Xiao, Jinliang Hu, Xiaohong Cheng
Novel discotic mesogens P/n-M (n = 12, 16, 18, M = 2H, Zn and Cu) bearing a porphyrin core, triazole linkages and peripheral 3,4,5-trialkoxybenzyl units have been synthesized by "click chemistry" approach. The thermal behavior, photophysical properties and morphologies of these compounds were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), X-ray diffraction (XRD), UV and PL spectra, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). These compounds can self-assemble into hexagonal columnar phases in their pure states and form organogels in 1,4-dioxane with unusually flower-like sphere morphology...
January 12, 2018: Chemistry, An Asian Journal
Fu-Ling Liu, Dong Li, Li-Jie Su, Jun Tao
A novel bent ligand-pillared three-dimensional Hofmann-type metal-organic framework, [FeII(Hbpt)Pt(CN)4]·1/2Hbpt·1/2CH3OH·5/2H2O [1, Hbpt = 4,4'-(1H-1,2,4-triazole-3,5-diyl) dipyridine], was synthesized and crystallographically and magnetically characterized, which showed incomplete three-step spin-crossover behavior with a reversible three equal-step sequence of HS1.00 ↔ HS0.75LS0.25 ↔ HS0.5LS0.5 ↔ HS0.25LS0.75.
January 12, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Kanokorn Wechakorn, Samran Prabpai, Kanoknetr Suksen, Phongthon Kanjanasirirat, Yongyut Pewkliang, Suparerk Borwornpinyo, Palangpon Kongsaeree
A rhodamine-based fluorescent chemodosimeter rhodamine hydrazide-triazole (RHT) tethered with a triazole moiety was developed for Cu2+ detection. In aqueous medium, the RHT probe exhibited high selectivity and sensitivity toward Cu2+ among other metal ions. The addition of Cu2+ triggered a fluorescence emission of RHT by 384-fold (Φ = 0.33) based on a ring-opening process and a subsequent hydrolysis reaction. Moreover, RHT also showed a selective colorimetric response toward Cu2+ from colorless solution to pink, readily observed with the naked eye...
February 2018: Luminescence: the Journal of Biological and Chemical Luminescence
Nicole Jenkins, Marion Black, Hans G Schneider
INTRODUCTION: Invasive fungal infections are an increasing cause of mortality and morbidity in high risk patient populations such as those on immunosuppressive therapy. Triazole antifungals are recommended for the prevention and treatment of such infections. The aim of this study was to develop and validate a simple, sensitive and robust LCMS/MS method for the simultaneous analysis in human plasma of three frequently used antifungal drugs: voriconazole, posaconazole, and itraconazole...
January 8, 2018: Clinical Biochemistry
Cristina Nastasă, Dan C Vodnar, Ioana Ionuţ, Anca Stana, Daniela Benedec, Radu Tamaian, Ovidiu Oniga, Brînduşa Tiperciuc
The global spread of bacterial resistance to drugs used in therapy requires new potent and safe antimicrobial agents. DNA gyrases represent important targets in drug discovery. Schiff bases, thiazole, and triazole derivatives are considered key scaffolds in medicinal chemistry. Fifteen thiazolyl-triazole Schiff bases were evaluated for their antibacterial activity, measuring the growth inhibition zone diameter, the minimum inhibitory concentration (MIC), and the minimum bactericidal concentration (MBC), against Gram-positive (Staphylococcus aureus, Listeria monocytogenes) and Gram-negative (Escherichia coli, Salmonella typhimurium, Pseudomonas aeruginosa) bacteria...
January 11, 2018: International Journal of Molecular Sciences
Geraldo Célio Brandão, Franciele C Rocha Missias, Lucas Miquéias Arantes, Luciana Ferreira Soares, Kuldeep K Roy, Robert J Doerksen, Alaide Braga de Oliveira, Guilherme Rocha Pereira
Lapachol is an abundant prenyl naphthoquinone occurring in Brazilian Bignoniaceae that was clinically used, in former times, as an antimalarial drug, despite its moderate effect. Aiming to search for potentially better antimalarials, a series of 1,2,3-triazole derivatives was synthesized by chemical modification of lapachol. Alkylation of the hydroxyl group gave its propargyl ether which, via copper-catalyzed cycloaddition (CuAAC) click chemistry with different organic azides, afforded 17 naphthoquinonolyl triazole derivatives...
December 24, 2017: European Journal of Medicinal Chemistry
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