- Predicting self-assembly and structure in diluted aqueous solutions of modified mono- and bis-β-cyclodextrins that contain naphthoxy chromophore groups
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The water diluted solution behaviour of mono- and bis-β-cyclodextrin (mono- and bis-CD) derivatives, whose appended groups and inter-CD linkers contain a naphthoxy chromophore moiety, has been studied using steady-state and time-resolved fluorescence techniques, circular dichroism and molecular modelling. Mono-CD derivatives form non-covalent dimeric tail-to-tail supramolecular structures via the mutual partial penetration, through their primary sides, of axially oriented naphthoxy appended groups and the self-inclusion of the naphthoxy moiety is rather improbable. Non-covalent dimer formation may compete with any guest complexation. Nevertheless, these assemblies can be broken up by decreasing medium polarity or when the appended group is captured by macrorings such as cucurbit[7]urils or native βCDs. Bis-CD derivatives, however, do not exhibit self-association processes which were observed in the mono-derivatives. This is because the presence of the bulky naphthoxy group in the spacer keeps the βCD cavities, which are capable of accommodating an external guest, away from each other. The dinaphthoxy group, in the bis-NβCD, was located in a quasi-parallel plane conformation between both CDs. This journal is
- Carmona, Thais,Martina, Katia,Rinaldi, Laura,Boffa, Luisa,Cravotto, Giancarlo,Mendicuti, Francisco
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- Design of novel anthracene-based fluorescence sensor for sensitive and selective determination of iron in real samples
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A dipodal fluorescence (FL) system based on an anthracene platform was prepared by a general synthetic strategy. The water-miscible receptor was characterized by MALDI-MS, 1H NMR, 13C NMR, and FT-IR. In order to the illustration of photophysical properties of the synthesized sensor, the excitation–emission matrix (EEM) analysis and 3D-fluorescence measurements were performed. Ultraviolet-Visible (UV–vis) and FL spectroscopies were carried out to evaluate the FL performance of the sensor. Low concentrations of iron ions (Fe3+) could be determined by this sensitive and simple sensor. Due to the quenching effect of Fe3+, a limit of detection (LOD) of 0.314 μM was obtained in the linear range of 0.3–130 μM. This fluorescent sensor was applied for measuring ferric ions in environmental water and tablet samples, which was highly efficient. The proposed strategy could be applied to develop sensors for not only for Fe3+ but also for many various metal ions using a diversity of fluorophores and ionophores.
- Haddad Irani-nezhad, Mahsa,Khataee, Alireza,Tümay, Süreyya O?uz
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- Tripodal synthetic receptors based on cyclotriphosphazene scaffold for highly selective and sensitive spectrofluorimetric determination of iron(III) in water samples
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Two novel tripodal synthetic receptors based on cyclotriphosphazene scaffolds were prepared for spectrofluorimetric quantification of iron ions in environmental water samples. The receptors were designed by using the planar structure of cyclotriphosphazene which were modified by metal ion detecting naphtalene or anthracene-triazole groups above the plane and water solubility interacting triethylene glycol monomethyl ether (TEGME) groups below. All compounds were characterized by standard spectroscopic techniques such as 1H, 13C, 31P NMR and mass spectrometry (MALDI-TOF). The new developed methods based selective and sensitive complexation of CBTSRs with iron prior to spectrofluorimetric determination without any preconcentration processes. The experimental conditions such as pH, buffer and buffer concentration, initial CBTSRs concentration and time before measurement were optimized for selective complexation, which provided submicromolar spectrofluorimetric determination of iron under optimized conditions. The obtained results demonstrated that CBTSRs led to develop sensitive (LODs, 0.54 and 0.44 μM), selective and time-saving spectrofluorimetric methods for quantification of iron ions in environmental water samples under the optimized conditions (pH, 7.0; initial CBTSRs concentration, 10 μM and 5 μM; solvent, aqueous ethanol, (3:1 v/v and 9:1 v/v); buffer and buffer concentration, 0.1 M Britton-Robinson buffer; time before measurement, 20 and 25 s).
- Tümay, Süreyya O?uz,Ye?ilot, Serkan
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- Cu(I) catalyzed coumarin-1,2,3-triazole hybrids: Click chemistry
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A series of novel coumarin-1,2,3-triazole derivatives were synthesized in good yield via click chemistry using Cu(I) catalyzed intermolecular Huisgen [3+2] cycloaddition reaction. All the synthesized compounds were characterized spectroscopically. This piece of work could be helpful to develop biologically relevant coumarin analogs.
- Mamgain, Ritu
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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 0083-0084
(2021/08/28)
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- A novel series of substituted 1,2,3-triazoles as cancer stem cell inhibitors: Synthesis and biological evaluation
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An alarming increase in global death toll resulting from cancer incidents, particularly due to multidrug resistance and reduced efficacy as a consequence of target mutations, has compelled us to look for novel anticancer agents. Cancer stem cells (CSCs),
- Padhariya, Komal N.,Athavale, Maithili,Srivastava, Sangeeta,Kharkar, Prashant S.
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- Application of artificially synthesized palladium nano-enzyme to catalysis of compound containing phenolic hydroxyl group connection
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The invention provides application of an artificially synthesized palladium nano-enzyme to catalysis of a compound containing phenolic hydroxyl connection. The palladium nano-enzyme is used for catalyzing breakage of a carbon-oxygen bond of propargyloxy connected with an aromatic functional group containing at least one benzene ring; the aromatic functional group containing at least one benzene ring comprises but is not limited to fluorescein, the benzene ring, a pyridine ring, biphenyl, naphthalene, anthracene, coumarin or camptothecin, and the aromatic functional group containing at least one benzene ring can be connected with oxygen or oxygen-carbonyl oxygen or oxygen-carbonyl oxygen-oxygen. By constructing different artificially synthesized palladium nano-enzymes, the carbon-oxygen bond breakage of various molecules can be realized, and the palladium nano-enzymes can be applied to cell imaging and cancer treatment.
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Paragraph 0038-0039; 0042-0043; 0048-0049
(2021/09/04)
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- TiO2/Cu2O nanoparticle-catalyzed direct C(sp)-P bond formation: Via aerobic oxidative coupling in air and visible light
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The synthesis of organophosphorus compounds is one of the important goals in organic chemistry. Among these compounds, alkynylphosphonates are significantly utilized as the main precursors for the synthesis of biologically active molecules in medicinal chemistry and have attracted extensive interest in the past few decades. Although few efforts have been made towards the direct and atom-economical synthesis of alkynylphosphonates, efforts towards the utilization of visible light as a green and renewable energy source have not been made to date. Here, we have promoted a strategy to construct a type of nano metal oxide composite photocatalyst (Cu2O decorated on TiO2) for the synthesis of alkynylphosphonates via direct C-P bond formation between terminal alkyne and H-phosphonate under visible light irradiation. In this p-n heterojunction photocatalyst, Cu2O acted as a visible-light absorber; moreover, the CB (conduction band) of TiO2 was favorable for accepting a photogenerated electron, and the generated electron hole (e-/h+) pair could initiate the reaction. The present study can provide a new way for the synthesis of this important class of phosphorus organic compounds.
- Hosseini-Sarvari, Mona,Jafari, Fattaneh
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supporting information
p. 3001 - 3006
(2020/03/13)
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- Synthesis and neuroprotective effects of novel chalcone-triazole hybrids
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The development of novel neuroprotective agents is urgently needed for the treatment of neurodegenerative diseases, affecting aging individuals worldwide. In this study, a new set of chalcone-triazole hybrids (6a-g) was synthesized and evaluated for their
- Sooknual, Pichjira,Pingaew, Ratchanok,Phopin, Kamonrat,Ruankham, Waralee,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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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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- 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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- Discovery of a novel series of hDHODH inhibitors with anti-pulmonary fibrotic activities
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Human dihydroorotate dehydrogenase (hDHODH) is a flavin-dependent enzyme essential to pyrimidine de novo biosynthesis, which serves as an attractive therapeutic target for the treatment of autoimmune disorders. A novel series of hDHODH inhibitors was deve
- Lu, Kuan,Zhao, Yanfang,Wu, Guodong,Hu, Hao,Wang, Mingzhong,Gong, Guowei,Jiang, Yuyang
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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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- Copper-Catalyzed Asymmetric Hydroboration of 2 H-Chromenes Using a Chiral Diphosphine Ligand
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A highly regioselective asymmetric hydroboration of 2H-chromenes catalyzed by the complex of CuCl and diphosphine ligand (S,R)-DuanPhos has been realized under mild conditions to produce 3-boryl chromans, achieving good yields and excellent enantioselectivities up to 96% ee. This work provides an efficient approach to the synthesis of chiral 3-boryl chromans and derivatives.
- Li, Xiufen,Wang, Chaoqiong,Song, Jianqiao,Yang, Zhihong,Zi, Guofu,Hou, Guohua
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p. 8638 - 8645
(2019/08/30)
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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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- Electrochemical C-H cyanation of electron-rich (Hetero)arenes
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A straightforward method for the electrochemical C-H cyanation of arenes and heteroarenes that proceeds at room temperature in MeOH, with NaCN as the reagent in a simple, open, undivided electrochemical cell is reported. The platinum electrodes are passivated by ad-sorbed cyanide, which allows conversion of an exceptionally broad range of electron-rich substrates all the way down to dialkyl arenes. The cyanide electrolyte can be replenished with HCN, opening opportunities for salt-free industrial C-H cyanation.
- Hayrapetyan, Davit,Rit, Raja K.,Kratz, Markus,Tschulik, Kristina,Goo?en, Lukas J.
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supporting information
p. 11288 - 11291
(2018/10/20)
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- Hit discovery of Mycobacterium tuberculosis inosine 5′-monophosphate dehydrogenase, GuaB2, inhibitors
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Tuberculosis remains a global concern. There is an urgent need of newer antitubercular drugs due to the development of resistant forms of Mycobacterium tuberculosis (Mtb). Inosine 5′-monophosphate dehydrogenase (IMPDH), guaB2, of Mtb, required for guanine nucleotide biosynthesis, is an attractive target for drug development. In this study, we screened a focused library of 73 drug-like molecules with desirable calculated/predicted physicochemical properties, for growth inhibitory activity against drug-sensitive MtbH37Rv. The eight hits and mycophenolic acid, a prototype IMPDH inhibitor, were further evaluated for activity on purified Mtb-GuaB2 enzyme, target selectivity using a conditional knockdown mutant of guaB2 in Mtb, followed by cross-resistance to IMPDH inhibitor-resistant SRMV2.6 strain of Mtb, and activity on human IMPDH2 isoform. One of the hits, 13, a 5-amidophthalide derivative, has shown growth inhibitory potential and target specificity against the Mtb-GuaB2 enzyme. The hit, 13, is a promising molecule with potential for further development as an antitubercular agent.
- Sahu, Niteshkumar U.,Singh, Vinayak,Ferraris, Davide M.,Rizzi, Menico,Kharkar, Prashant S.
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supporting information
p. 1714 - 1718
(2018/05/05)
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- Synthesis and evaluation of naphthyl bearing 1,2,3-triazole analogs as antiplasmodial agents, cytotoxicity and docking studies
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Novel series of naphthyl bearing 1,2,3-triazoles (4a–t) were synthesized and evaluated for their in vitro antiplasmodial activity against pyrimethamine (Pyr)-sensitive and resistant strains of Plasmodium falciparum. The synthesized compounds were assessed
- Balabadra, Saikrishna,Kotni, MeenaKumari,Manga, Vijjulatha,Allanki, Aparna Devi,Prasad, Rajesh,Sijwali, Puran Singh
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p. 221 - 232
(2016/12/23)
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- Synthesis of new 1,2,3-triazole linked benzimidazole molecules as anti-proliferative agents
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One pot click chemistry is used to link triazole and benzimidazole pharmacophore to get N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)aniline and its derivatives. Flexible linkages in the form of –CH2–R or –O–R/–N–R were designed during synthesis. All the newly synthesized compounds were characterized by FT-IR and NMR spectroscopy as well as high-resolution mass spectrometry. Selected compounds were screened for in vitro anti-proliferative activity using National Cancer Institute (NCI)-60 human tumor cell line screening program. The most potent structure N-((1-((1H-benzo[d]imidazol-2-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-4-chloroaniline 7e showed 40% growth inhibition in renal cancer cell line (UO-31) at 10 μM concentration.
- Sahay, Ishani I.,Ghalsasi, Prasanna S.
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supporting information
p. 825 - 834
(2017/04/06)
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- Regioselective synthesis, characterization and antimicrobial evaluation of amide–ether-linked 1,4-disubstituted 1,2,3-triazoles
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Regioselective synthesis of some amide–ether-linked 1,4-disubstit-uted 1,2,3-triazoles was realized via the copper(I)-catalyzed click reaction of 1-(prop-2-ynyloxy)naphthalene, 2-(prop-2-ynyloxy)naphthalene and 1,4-bis-(prop-2-ynyloxy)benzene with 2-azido-N-substituted acetamides. The synthesized compounds were characterized by spectral techniques viz. FT-IR,1H--NMR,13C-NMR, HRMS and evaluated for their in vitro antimicrobial activity against Bacillus subtilis, Staphylococcus aureus (Gram-positive bacteria), Pseudomonas aeruginosa, Escherichia coli (Gram-negative bacteria), Candida albicans and Aspergillus brasiliensis (fungi). Among the synthesized 1,4--disubstituted 1,2,3-triazoles, compound 13d displayed excellent antibacterial potential, while, compounds 7d and 13d appeared as potent fungicidal agents against the tested microbial strains. The docking simulation of the broad spectrum microbicidal disubstituted 1,2,3-triazole 13d into the active site of E. coli type II topoisomerase, DNA gyrase B enzyme was also investigated.
- Kaushik, Chander Prakash,Kumar, Krishan,Kumar, Devinder,Mor, Satbir,Kumar, Ashwani,Jindal, Deepak Kumar
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p. 995 - 1007
(2017/10/13)
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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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p. 23680 - 23686
(2017/07/07)
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- Thermally Induced Denitrogenative Annulation for the Synthesis of Dihydroquinolinimines and Chroman-4-imines
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A rapid growth in synthetic methods for the preparation of diverse organic molecules using N-sulfonyl-1,2,3-triazoles is of great interest in organic synthesis. Transition metals are generally used to activate the α-imino diazo intermediates. Metal-free methods have not been studied in detail, but can be a good complement to transition metal catalysis in the mild reaction conditions. We herein report a novel method for the preparation of 2,3-dihydroquinolin-4-imine and chroman-4-imine analogs from their corresponding N-sulfonyl-1,2,3-triazoles in the absence of metal catalysts. To achieve intramolecular annulation, the introduction of an electron-donating group is required at the meta position of N-sulfonyl-1,2,3-triazole methyl anilines. The inclusion of tailored substituents on the aniline moieties and nitrogen atoms enhances the nucleophilicity of the phenyl π-electrons, thus allowing them to undergo a Friedel-Crafts-type reaction with the highly electrophilic ketenimines. This metal-free method was carefully optimized to generate a variety of dihydroquinolin-4-imines and chroman-4-imines in moderate-to-good yields.
- Chou, Chih-Hung,Chen, Ying-Yu,Rajagopal, Basker,Tu, Hsiu-Chung,Chen, Kuan-Lin,Wang, Sheng-Fu,Liang, Chien-Fu,Tyan, Yu-Chang,Lin, Po-Chiao
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supporting information
p. 757 - 765
(2016/03/09)
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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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- 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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- Gold(I)-Catalyzed Dearomative [2+2]-Cycloaddition of Indoles with Activated Allenes: A Combined Experimental-Computational Study
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The gold-catalyzed synthesis of methylidene 2,3-cyclobutane-indoles is documented through a combined experimental/computational investigation. Besides optimizing the racemic synthesis of the tricyclic indole compounds, the enantioselective variant is pres
- Ocello, Riccardo,De Nisi, Assunta,Jia, Minqiang,Yang, Qing-Qing,Monari, Magda,Giacinto, Pietro,Bottoni, Andrea,Miscione, Gian Pietro,Bandini, Marco
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supporting information
p. 18445 - 18453
(2015/12/24)
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- Synthesis of Potential Bioactive Novel 7-[2-Hydroxy-3-(1,2,3-triazol-1-yl) propyloxy]-3-alkyl-4-methylcoumarins
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A series of 50 novel 7-[2-hydroxy-3-(1,2,3-triazol-1-yl)propyloxy]-3-alkyl-4-methylcoumarins had been designed and synthesized in good to excellent yields via Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction "click chemistry" of 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarins with variety of acetylene derivatives. In turn, the precursor compound, that is, 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarin, was synthesized by condensation of epichlorohydrin with 7-hydroxy-3-alkyl-4-methylcoumarins followed by opening of the epoxide ring in the resulted 7-epoxymethoxy-3-alkyl-4-methylcoumarins with sodium azide. All the synthesized compounds were unambiguously identified on the basis of their spectral data analyses (IR, 1H-NMR, 13C-NMR spectra, and HRMS).
- Arya, Anu,Kumar, Vinod,Mathur, Divya,Singh, Sukhdev,Brahma, Raju,Singh, Rajpal,Singh, Seema,Sharma,Parmar, Virinder S.,Prasad, Ashok K.
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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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- 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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- A convenient method for the synthesis of (prop-2-ynyloxy)benzene derivatives via reaction with propargyl bromide, their optimization, scope and biological evaluation
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A highly convenient method has been developed for the synthesis of (prop-2-ynyloxy) benzene and its derivatives. Differently substituted phenol and aniline derivatives were allowed to react with propargyl bromide in the presence of K2CO3/
- Batool, Tannaza,Rasool, Nasir,Gull, Yasmeen,Noreen, Mnaza,Nasim, Faiz-Ul-Hassan,Yaqoob, Asma,Zubair, Muhammad,Rana, Usman Ali,Ud-Din Khan, Salah,Zia-Ul-Haq,Jaafar, Hawa Z. E.
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- Four-component, one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles bearing 1-(2-phenylselenocyclohexyl) group
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An efficient, one-pot, three-step, regioselective synthesis of 4-substituted 1-(2-phenylselenocyclohexyl)-1,2,3-triazoles, involving in situ generation of l-azido-2-phenylselenocyclohexane has been developed via four-component reaction of phenylselenenyl
- Sheng, Wusheng,Sheng, Shouri,Zeng, Jiangbo,Huang, Zhenzhong,Cai, Mingzhong
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p. E222-E226
(2014/11/07)
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- Design, synthesis and molecular docking studies of novel N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinoline-based triazoles with potential anticancer activity
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A novel series of N-benzenesulfonyl-1,2,3,4-tetrahydroisoquinolines (14-33) containing triazole moiety were designed and synthesized through rational cycloadditions using the modified Pictet-Spengler reaction and the Click chemistry. Antiproliferative act
- Pingaew, Ratchanok,Mandi, Prasit,Nantasenamat, Chanin,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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p. 192 - 203
(2014/06/09)
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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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- Chemoenzymatic synthesis of 3'-deoxy-3'-(4-substituted-triazol-1-YL)-5- methyluridine
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An efficient protocol has been developed for the synthesis of a small library of 3'-deoxy-3'- (4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3- dipolar cycloaddition reaction of 3'-azido-3'-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3'-azido-3'-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K2CO3 in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, 1H-, 13C NMR spectra, and high-resolution mass spectra) data analysis.
- Arya, Anu,Mathur, Divya,Tyagi, Abhilash,Kumar, Rajesh,Kumar, Vinod,Olsen, Carl E.,Saxena, Rajendra K.,Prasad, Ashok K.
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p. 646 - 659
(2014/01/06)
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- Clicking 3′-azidothymidine into novel potent inhibitors of human immunodeficiency virus
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3′-Azidothymidine (AZT) was the first approved antiviral for the treatment of human immunodeficiency virus (HIV). Reported efforts in clicking the 3′-azido group of AZT have not yielded 1,2,3-triazoles active against HIV or any other viruses. We report herein the first AZT-derived 1,2,3-triazoles with submicromolar potencies against HIV-1. The observed antiviral activities from the cytopathic effect (CPE) based assay were confirmed through a single replication cycle assay. Structure-activity-relationship (SAR) studies revealed two structural features key to antiviral activity: a bulky aromatic ring and the 1,5-substitution pattern on the triazole. Biochemical analysis of the corresponding triphosphates showed lower ATP-mediated nucleotide excision efficiency compared to AZT, which along with molecular modeling suggests a mechanism of preferred translocation of triazoles into the P-site of HIV reverse transcriptase (RT). This mechanism is corroborated with the observed reduction of fold resistance of the triazole analogue to an AZT-resistant HIV variant (9-fold compared to 56-fold with AZT).
- Sirivolu, Venkata Ramana,Vernekar, Sanjeev Kumar V.,Ilina, Tatiana,Myshakina, Nataliya S.,Parniak, Michael A.,Wang, Zhengqiang
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supporting information
p. 8765 - 8780
(2013/12/04)
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- Traceless sulfone linker for the solid-phase organic synthesis of 1-(E)-styryl-4-substituted-1,2,3-triazoles
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A novel, facile, solid-phase, organic synthesis of 1-(E)-styryl-4- substituted-1,2,3-triazoles in good yields and purities via traceless sulfone linker has been developed. Key steps involved in this synthetic procedure include (i) sulfone alkylation of su
- Jiang, Jian-Wen,Sheng, Shou-Ri,Zhang, Xiao-Lan,Fang, Zheng,Cai, Ming-Zhong
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p. 2784 - 2792
(2013/08/23)
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- Synthesis, structure, and growth-promoting activity of 1-alkyl-4-(3- naphthyloxyprop-1-ynyl)piperidin-4-ols
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Alkylation of 1- and 2-naphthols with propargyl bromide in acetone in the presence of potassium carbonate led to prop-2-ynyloxynaphthalenes, which upon reaction with 1-alkyl-piperidin-4-ones under the Favorsky conditions afforded the corresponding tertiary alcohols. 1-Methyl-4-[3-(2-naphthyloxy)prop-1-ynyl] piperidin-4-ol hydrochloride was found to possess a high growth-promoting activity in the concentration of 0.001% upon the pre-sowing treatment of beetroot seeds and potatoes and increase their productivity by -20%.
- Omirzak,Erkasov,Sukhov,Ganenko
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p. 2442 - 2444
(2014/11/07)
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- Palladium-catalyzed trifluoroethylation of terminal alkynes with 1,1,1-trifluoro-2-iodoethane
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An efficient Csp-CH2CF3 bond-forming reaction via Pd-catalyzed 2,2,2-trifluoroethylation of aryl and alkyl terminal alkynes has been developed. This protocol proceeds under mild conditions using the readily available and cheap reagent CF3CH2I as the source of the CH2CF3 group. Various terminal aryl alkynes as well as alkylacetylenes can be transformed into the corresponding trifluoroethylated products in good-to-excellent yields. The method is tolerant of carbonyl, nitro, ester, cyano, and even formyl groups.
- Feng, Yi-Si,Xie, Chuan-Qi,Qiao, Wen-Long,Xu, Hua-Jian
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supporting information
p. 936 - 939
(2013/03/28)
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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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- 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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- 4-Deoxy-4-fluoro-xyloside derivatives as inhibitors of glycosaminoglycan biosynthesis
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Various 4-deoxy-4-fluoro-xylosides were prepared using click chemistry for evaluating their potential utility as inhibitors of glycosaminoglycan biosynthesis. 2,3-Di-O-benzoyl-4-deoxy-4-fluoro-β-d-xylopyranosylazide, obtained from l-arabinopyranose by six
- Tsuzuki, Yasuhiro,Nguyen, Thao Kim Nu,Garud, Dinesh R.,Kuberan, Balagurunathan,Koketsu, Mamoru
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supporting information; experimental part
p. 7269 - 7273
(2011/01/12)
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- Synthesis of organochalcogen propargyl aryl ethers and their application in the electrophilic cyclization reaction: An efficient preparation of 3-halo-4-chalcogen-2H-benzopyrans
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We herein described the synthesis of various organochalcogen propargyl aryl ethers via reaction of lithium acetylide intermediate with electrophilic chalcogen (sulfur, selenium, tellurium) species. Various aryl and alkyl groups directly bonded to the chal
- Godoi, Benhur,Speranca, Adriane,Back, Davi F.,Brandao, Ricardo,Nogueira, Cristina W.,Zeni, Gilson
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body text
p. 3469 - 3477
(2009/09/06)
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- Synthesis of functionalized β-cyclodextrins by "click chemistry"
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Two new β-cyclodextrins (β-CDs) modified with chromophore were synthesized in high yields through Huisgen 1,3-dipolar cycloaddition. The amount of Cu catalyst was demonstrated to be a key factor that determines the yield of the 1,3-dipolar cycloaddition when applied to CD derivatization. While a catalytic amount of Cu-catalyst is commonly required in conventional click chemistry, more than a half equivalent of Cu catalyst was desirable for obtaining the modified CDs in satisfactory yields. The Japan Institute of Heterocyclic Chemistry.
- Ke, Chenfeng,Yang, Cheng,Yang, Zixin,Wu, Weijia,Mori, Tadashi,Inoue, Yoshihisa,Liu, Yu
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experimental part
p. 155 - 160
(2011/03/22)
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- Facile synthesis of α,β-acetylenic ketones and 2,5-disubstituted furans: Consecutive activation of triple and double bond with ZnBr2 toward the synthesis of furan ring
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α,β-Acetylenic ketones were synthesized from the reaction of acid chlorides and acetylenic compounds in the presence of ZnBr2 and DIEA in acetonitrile. From the acetylenic ketones having nearby methylene unit, 2,5-disubstituted furan derivatives could be synthesized under the same reaction conditions.
- Lee, Ka Young,Lee, Mi Jung,Kim, Jae Nyoung
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p. 8705 - 8710
(2007/10/03)
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- Cesium fluoride-mediated claisen rearrangement of aryl propargyl ether. Exclusive formation of 2-methylarylfuran and its availability as a masked salicylaldehyde
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Claisen rearrangement of an aryl propargyl ether in the presence of CsF led to exclusive formation of 2-methylarylfuran in excellent yield. The result of a precise examination of the rearrangement is described. Satisfactory transformation of the 2-methyla
- Ishii,Ishikawa,Takeda,Ueki,Suzuki
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p. 1148 - 1153
(2007/10/02)
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- Thermal and catalytic Claisen rearrangement of propargyl ethers of isomeric acetylnaphthols and 4,6-diacetylresorcinol
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The Claisen rearrangement of the propargyl ethers (2 and 6) of isomeric 2-acetyl-1-naphthol (1) and 1-acetyl-2-naphthol (5) and of bispropargyl ether (11) of 4,6-diacetylresorcinol (10) has been studied under thermal and catalytic conditions like, (i) ref
- Anjaneyulu A S R,Isaa, B Meher
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p. 828 - 833
(2007/10/02)
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- 142. Thermal rearrangements of halogen substituted aryl propargyl ethers
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7-Chloro-2-chloromethyl-benzofuran (13) and 3, 8-dichloro-2H-1-benzopyran (12) are the main products from the thermal rearrangement (230-260°) of 2, 6-dichlorophenyl propargyl ether (7). Compounds 17, 18 and 19 are also formed, but in much smaller amounts
- Sarcevic, Nada,Zsindely, Janos,Schmid, Hans
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p. 1457 - 1476
(2007/10/04)
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