- Synthesis of alkynylated 1,2,4-oxadiazole/1,2,3-1H-triazole glycoconjugates: Discovering new compounds for use in chemotherapy against lung carcinoma and Mycobacterium tuberculosis
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A total of forty-three compounds were synthesized, including thirty-two new ones. Among those compounds, seventeen were selected and tested on human tumor cell lines: PC-3 (prostate adenocarcinoma), HCT-116 (colorectal tumor), NCIH-460 (lung carcinoma), S
- Melo de Oliveira, Valentina Nascimento,Flávia do Amaral Moura, Cybele,Peixoto, Aline dos Santos,Gon?alves Ferreira, Vanessa Pinheiro,Araújo, Héverton Mendes,Lapa Montenegro Pimentel, Lilian Maria,Pessoa, Claudia do ó,Nicolete, Roberto,Versiani dos Anjos, Janaína,Sharma, Prem Prakash,Rathi, Brijesh,Pena, Lindomar José,Rollin, Patrick,Tatibou?t, Arnaud,Nascimento de Oliveira, Ronaldo
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- Multitasking with Chemical Fuel: Dissipative Formation of a Pseudorotaxane Rotor from Five Distinct Components
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A 3-fold completive self-sorted library of dynamic motifs was integrated into the design of the pseudorotaxane-based rotor [Zn(2·H+)(3)(4)]2+ operating at k298 = 15.4 kHz. The rotational motion in the five-component device is based on association/dissocia
- Ghosh, Amit,Paul, Indrajit,Schmittel, Michael
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supporting information
p. 5319 - 5323
(2021/05/04)
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- Amidine-and amidoxime-substituted heterocycles: Synthesis, antiproliferative evaluations and dna binding
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The novel 1,2,3-triazolyl-appended N-and O-heterocycles containing amidine 4–11 and amidoxime 12–22 moiety were prepared and evaluated for their antiproliferative activities in vitro. Among the series of amidine-substituted heterocycles, aromatic diamidin
- Grb?i?, Petra,Kraljevi? Paveli?, Sandra,Mara?i?, Silvija,Paveli?, Kre?imir,Radi? Stojkovi?, Marijana,Rai?-Mali?, Silvana,Sedi?, Mirela,Shammugam, Suresh
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- Ammonium Chloride-Promoted Rapid Synthesis of Monosubstituted Ureas under Microwave Irradiation
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Monosubstituted ureas are important scaffolds in organic chemistry. They appear in various biologically active compounds and serve as versatile precursors in synthesis. Monosubstituted ureas were originally prepared using toxic and hazardous phosgene equivalents. Modern methods include transamidation of urea and nucleophilic addition to cyanate salts, both of which suffer from a narrow substrate scope due to the need for a strong acid and prolonged reaction times. We hereby report that ammonium chloride can promote the reaction between amines and potassium cyanate to generate monosubstituted ureas in water. This method proceeds rapidly under microwave irradiation and tolerates a broad range of functional groups. Unlike previous strategies, it is compatible with other nucleophiles, acid-labile moieties, and most of the common protecting groups. The products precipitate out of solution, allowing facile isolation without column chromatography.
- Lan, Chunling Blue,Auclair, Karine
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supporting information
p. 5135 - 5146
(2021/10/19)
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- Light-emitting diode light–enabled denitrative etherification of 4-nitrobenzonitrile under catalyst-free conditions at room temperature
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In this study, we have developed a catalyst-free procedure for denitrative etherification of electron-deficient nitroarenes. In this method, the reaction failed in the dark but was enabled by white light-emitting diode light (6 W) in the presence of NaOH/dimethylformamide at room temperature with short reaction times. Interestingly, the reaction in the dark is completed almost immediately once a small quantity of water is added to the reaction mixture. Ultraviolet irradiation (λ = 254 nm) was not effective for this reaction to proceed.
- Soltani, Roghaye,Abdollahi, Fatemeh,Ghaderi, Arash
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- Uniform copper nanoparticles as an inexpensive and efficient catalyst for synthesis of novel β-carbonyl-1, 2, 3-triazoles in water medium
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Copper nanoparticles as an efficient, inexpensive catalyst were prepared via ball milling for synthesis of β-carbonyl 1, 2, 3-triazoles from azido alcohol by click reaction in water. An extensive range of raw materials such as sodium azide, phenacyl bromi
- Esmaeili-Shahri, Hadi,Eshghi, Hossein,Lari, Jalil,Rounaghi, Seyyed Amin,Esmaeili-Shahri, Effat
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p. 2963 - 2979
(2019/03/13)
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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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- Coumarin-1,2,3-triazole hybrid derivatives: Green synthesis and DFT calculations
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A series of new 1,2,3-triazole-coumarin hybrid system are synthesized from the click reaction between 3-azido coumarin and different aromatic terminal alkyne derivatives in a green manner. All compounds are characterized by IR, NMR and UV–VIS spectroscopy
- Nouraie, Pegah,Moradi Dehaghi, Shahram,Foroumadi, Alireza
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p. 386 - 394
(2019/01/19)
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- Interaction of carborane-appended trimer with bovine serum albumin: A spectroscopic investigation
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The interaction of symmetrical triazine-cored carborane-appended trimer 5 with bovine serum albumin has been investigated using different spectroscopic methods. The intrinsic fluorescence of BSA was quenched by the carborane trimer 5 through the dynamic q
- Jena, Bibhuti Bhusan,Satish, Lakkoji,Mahanta, Chandra Sekhara,Swain, Biswa Ranjan,Sahoo, Harekrushna,Dash, Barada P.,Satapathy, Rashmirekha
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- Small Molecule Inhibition of MicroRNA miR-21 Rescues Chemosensitivity of Renal-Cell Carcinoma to Topotecan
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Chemical probes of microRNA (miRNA) function are potential tools for understanding miRNA biology that also provide new approaches for discovering therapeutics for miRNA-associated diseases. MicroRNA-21 (miR-21) is an oncogenic miRNA that is overexpressed in most cancers and has been strongly associated with driving chemoresistance in cancers such as renal cell carcinoma (RCC). Using a cell-based luciferase reporter assay to screen small molecules, we identified a novel inhibitor of miR-21 function. Following structure-activity relationship studies, an optimized lead compound demonstrated cytotoxicity in several cancer cell lines. In a chemoresistant-RCC cell line, inhibition of miR-21 via small molecule treatment rescued the expression of tumor-suppressor proteins and sensitized cells to topotecan-induced apoptosis. This resulted in a >10-fold improvement in topotecan activity in cell viability and clonogenic assays. Overall, this work reports a novel small molecule inhibitor for perturbing miR-21 function and demonstrates an approach to enhancing the potency of chemotherapeutics specifically for cancers derived from oncomir addiction.
- Naro, Yuta,Ankenbruck, Nicholas,Thomas, Meryl,Tivon, Yaniv,Connelly, Colleen M.,Gardner, Laura,Deiters, Alexander
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supporting information
p. 5900 - 5909
(2018/08/04)
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- 1,4-Substituted Triazoles as Nonsteroidal Anti-Androgens for Prostate Cancer Treatment
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Prostate cancer (PC) is the fifth leading cause of cancer death in men, and the androgen receptor (AR) represents the primary target for PC treatment, even though the disease frequently progresses toward androgen-independent forms. Most of the commerciall
- Ferroni, Claudia,Pepe, Antonella,Kim, Yeong Sang,Lee, Sunmin,Guerrini, Andrea,Parenti, Marco Daniele,Tesei, Anna,Zamagni, Alice,Cortesi, Michela,Zaffaroni, Nadia,De Cesare, Michelandrea,Beretta, Giovanni Luca,Trepel, Jane B.,Malhotra, Sanjay V.,Varchi, Greta
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supporting information
p. 3082 - 3093
(2017/04/21)
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- 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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- N-Heterocyclic carbene-mediated redox condensation of alcohols
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N-Heterocyclic carbenes (NHCs) with a variety of oxidants promote the Mitsunobu-type coupling reactions of alcohols with phenols, carboxylic acids, and phthalimide. Experiments using a chiral alcohol indicate that these reactions proceed via SN1 or SN2 pathways depending on the polarity of the used solvents. The NHCs are consumed as reducing reagents to form their oxides as readily separable byproducts.
- Kato, Terumasa,Matsuoka, Shin-Ichi,Suzuki, Masato
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supporting information
p. 8569 - 8572
(2016/07/13)
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- A Fluorescent and Switchable Rotaxane Dual Organocatalyst
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Rotaxane organocatalysis presents a new direction toward controlled one-pot catalytic reactions. By combining molecular switches and catalysts, fluorescence and pH-responsive switching along with the exclusive selectivity of dual catalytic reactions are d
- Kwan, Chak-Shing,Chan, Albert S. C.,Leung, Ken Cham-Fai
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supporting information
p. 976 - 979
(2016/03/15)
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- Improved schmidt conversion of aldehydes to nitriles using azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-Propanol
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The Schmidt reaction of aromatic aldehydes using a substoichiometric amount (40 mol %) of triflic acid is described. Low catalyst loading was enabled by a strong hydrogen-bond-donating solvent hexafluoro-2-propanol (HFIP). This improved protocol tolerates a broad scope of aldehydes with diverse functional groups and the corresponding nitriles were obtained in good to high yields without the need for aqueous work up.
- Motiwala, Hashim F.,Yin, Qin,Aubé, Jeffrey
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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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- White-light-emitting edge-functionalized graphene quantum dots
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Graphene quantum dots (GQDs) have received considerable attention for their potential applications in the development of novel optoelectronic materials. In the generation of optoelectronic devices, the development of GQDs that are regulated in terms of their size and dimensions and are unoxidized at the sp2 surfaces is desired. GQDs functionalized with bulky Frechet's dendritic wedges at the GQD periphery were synthesized. The single-layered, size-regulated structures of the dendronized GQDs were revealed by atomic force microscopy. The edge-functionalization of the GQDs led to white-light emission, which is an uncommon feature. In the dotlight: Graphene quantum dots (GQDs) functionalized with bulky Frechet's dendritic wedges at the GQD periphery were synthesized. The single-layered, size-regulated structures of the dendronized GQDs were revealed by atomic force microscopy. The edge-functionalization of the GQDs led to white-light emission, which is an uncommon feature.
- Sekiya, Ryo,Uemura, Yuichiro,Murakami, Hideki,Haino, Takeharu
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supporting information
p. 5619 - 5623
(2014/06/10)
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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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- 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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- 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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- A non-metal catalysed oxidation of primary azides to nitriles at ambient temperature
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A novel non-metal catalyzed oxidation of organic azides to nitriles under solvent-free conditions is presented employing catalytic amounts of KI, and DABCO in aq. TBHP at room temperature. This non-metal catalyzed oxidation of azides provides good selectivity as double and triple bonds were not oxidized under the present reaction conditions. The Royal Society of Chemistry 2012.
- Lamani, Manjunath,Devadig, Pradeep,Prabhu, Kandikere Ramaiah
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p. 2753 - 2759
(2012/11/07)
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- A novel oxidative transformation of alcohols to nitriles: An efficient utility of azides as a nitrogen source
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An efficient methodology to oxidize benzylic and cinnamyl alcohols to their corresponding nitriles in excellent yields has been developed. This methodology employs DDQ as an oxidant and TMSN3 as a source of nitrogen in the presence of a catalytic amount of Cu(ClO4)2·6H 2O.
- Rokade, Balaji V.,Malekar, Sanjeev K.,Prabhu, Kandikere Ramaiah
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supporting information; experimental part
p. 5506 - 5508
(2012/07/03)
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- Chemoselective Schmidt reaction mediated by triflic acid: Selective synthesis of nitriles from aldehydes
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An excellent utility of Schmidt reaction of aldehydes to access corresponding nitriles in an instantaneous reaction is demonstrated. The reaction of aldehydes with NaN3 and TfOH furnishes the corresponding nitriles in near quantitative yields and tolerates a variety of electron-withdrawing and electron-donating substituents on the substrates. Formanilides, a common side product in Schmidt reaction, is not observed in this reaction. Besides these advantages, the salient feature of this reaction is that it exhibits a remarkable chemoselectivity, as acid and ketone functionalities are well tolerated under the reaction conditions. The reaction is easily scalable, high yielding, and nearly instantaneous.
- Rokade, Balaji V.,Prabhu, Kandikere Ramaiah
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experimental part
p. 5364 - 5370
(2012/09/07)
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- A twin-axial hetero[7]rotaxane
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Two in one: Two pseudorotaxanes can be combined to form a twin-axial hetero[7]rotaxane (see picture) by using the copper-catalyzed alkyne-azide "click" reaction. The synthetic route, in which twin-axial and single-axial rotaxanes are formed, combines self
- Zhang, Zhi-Jun,Zhang, Heng-Yi,Wang, Hui,Liu, Yu
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supporting information; experimental part
p. 10834 - 10838
(2011/12/16)
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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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- Solid state polymerization of diacetylenes with amide groups
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Two diacetylene derivatives (1, 2) carrying amide groups were prepared in order to control their packing arrangements by intermolecular hydrogen bonds. 1, 6-Bis(4- acetamidomethylphenoxy)-2,4-hexadiyne 1 is a symmetric diamide, which showed no changes by
- Okuno, Tsunehisa,Yamane, Kentaro,Sandman, Daniel J.
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- 16-Substituted polyunsaturated hexadecanoic fatty acids
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Sixteen carbon atom carboxylic acids having 16-phenoxy or 16-phenylthio substituents, and 0, 1, or 4 triple bonds, methods of preparing them, and pharmaceutical preparations containing them. These compounds are useful as lipoxygenase inhibitors.
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