- Synthesis of 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones and their application in asymmetric alkylation reaction
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New 1,2,3-triazolium ionic liquid-supported chiral imidazolidinones were developed. The feasibility of the ionic liquid-supported imidazolidinones as chiral auxiliaries was demonstrated in sequential propionylation-alkylation-cleavage reactions, which provided the chiral product with good to excellent chemical yields (up to 90%) and high selectivities (up to 94% ee). The progress of the reactions could be monitored by TLC and NMR, and the ionic liquid-supported chiral auxiliaries could be recovered by simple extraction.
- Jeong, Yunkyung,Park, Yunjeong,Ryu, Jae-Sang
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- Manganese complexes with chelating and bridging di-triazolylidene ligands: synthesis and reactivity
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New manganese complexes bearing di-triazolylidene (di-trz) ligands are described. Depending on the wingtip substituents of the triazolylidene ligand and the synthetic procedure, two different ligand coordination modes were observed,i.e, bridging and chelating. A series of Mn(i) complexes of the general typefac-[Mn(di-trzR)(CO)3Br] (R = Me, Et, Mes) with a chelating di-trz ligand were preparedviaAg-transmetalation. In contrast, thein situdeprotonation of the triazolium salts with KOButyielded the bimetallic Mn(0) complexes [Mn2(CO)8(μ-di-trzR)] with a bridging di-trz ligand when short alkyl chains (Me, Et, i-Pr) are present as the N1 substituents of the triazolylidene ligand. The molecular structures of monometallic and bimetallic complexes were determined by X-ray diffraction studies. In addition, the cationicfac-[Mn(di-trzEt)(CO)2(PPh3)2]Br complex, a rare example of a dicarbonyl Mn(i) N-heterocyclic carbene, was obtained whenfac-[Mn(di-trzEt)(CO)3Br] was irradiated with visible light in the presence of PPh3. The crystal structure revealed a slightly distorted octahedral geometry around the Mn(i) centre, with the chelating di-triazolylidene ligand situated intransposition to the two CO ligands in the equatorial plane, and the two phosphine ligands occupying the axial positions. Cyclic voltammetry studies show reversible redox processes for the monometallic Mn(i) complexes, and a quasi-reversible EC mechanism for the oxidation of the bimetallic complexes. Infrared spectroelectrochemical studies along with DFT calculations forfac-[Mn(di-trzEt)(CO)3Br] suggest that the observed two consecutive reductions both occur at the metal centre.
- Fri?es, Sofia,Realista, Sara,Gomes, Clara S. B.,Martinho, Paulo N.,Veiros, Luis F.,Albrecht, Martin,Royo, Beatriz
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- SUBSTITUENT EFFECTS ON PHYSICAL PROPERTIES OF AZOLE BASED IONIC LIQUIDS
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We investigated the effect of the substituents on the physical properties of azole based ionic liquids, such as melting point and viscosity. The introduction of electron-withdrawing groups to azolate anions and electron-donating groups to azolium cations delocalized the charge of anion or cation, and reduced the viscosity and melting point of the ionic liquids. The charge of the azolium cations and the azolate anions are distributed not only on the azole ring but also on the substituents. The decrease in the charge density of anions and cations in ionic liquids weakens the interaction between the anions and the cations, resulting in a decrease in the viscosity of the ionic liquids. Such a method of delocalizing the anion and cation charges of triazole-based ionic liquids by introduction of the substituents can be applied to reduce the viscosity of various ionic liquids as reaction medium and electrolytes.
- Kitaoka, Satoshi,Nishinaka, Shinnosuke,Nobuoka, Kaoru
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p. 275 - 287
(2022/02/16)
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- NITRIFICATION INHIBITORS
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The present invention generally relates to nitrification inhibitors and compositions comprising nitrification inhibitors. The present invention also relates to use of the nitrification inhibitors and compositions for application to fertilisers, plants, agricultural areas (e.g. soils or pastures) to reduce or inhibit the oxidation of ammonium nitrogen to nitrite and nitrate nitrogen, such as the oxidation of ammonia- or urea-based fertilisers.
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Page/Page column 35-38
(2021/03/13)
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- Design, Synthesis, Radiosynthesis and Biological Evaluation of Fenretinide Analogues as Anticancer and Metabolic Syndrome-Preventive Agents
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Fenretinide (4-HPR) is a synthetic derivative of all-trans-retinoic acid (ATRA) characterised by improved therapeutic properties and toxicological profile relative to ATRA. 4-HPR has been mostly investigated as an anti-cancer agent, but recent studies sho
- Patruno, Ilaria,Thompson, Dawn,Dall'Angelo, Sergio,Windhorst, Albert D.,Vugts, Danielle J.,Poot, Alex J.,Mody, Nimesh,Zanda, Matteo
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p. 1579 - 1590
(2020/07/13)
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- Furfuryl Cation Induced Three-Component Reaction to Synthesize Triazole-Substituted Thioesters
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A furfuryl cation induced three-component thioesterification reaction between thiols, 5-bromo-2-furylcarbinols and azides is reported. This metal-free method relies on the acetyl chloride/HFIP-mediated cascade formal [3+2] cycloaddition/ring-opening/thioesterification, which allows the efficient construction of a series of complex triazole-thioesters linked with an (Z)-olefin. Selenols are also suitable for this strategy. Further derivatization of thioesters highlighted the potential utility of our method.
- Zhong, Ying,Xu, Xiaoming,Xing, Qingzhao,Yang, Song,Gou, Jing,Gao, Ziwei,Yu, Binxun
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supporting information
p. 3251 - 3256
(2020/05/25)
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- PEG-DIL-based MnCl42?: A novel phase transfer catalyst for nucleophilic substitution reactions of benzyl halides
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Poly(ethylene glycol) dicationic ionic liquid-based MnCl42? was prepared by nucleophilic substitution of poly(ethylene glycol) dichloride with methylimidazole followed by reaction with MnCl2. The structural properties of the catalyst were systematically investigated using Fourier transform infrared, UV–visible and Raman spectra and thermogravimetric analysis. The application of this catalyst allows the synthesis of a variety of benzyl thiocyanates and azides in high yield under reflux conditions in water. The main advantages of this method are its easy nature, rapidity, environmental benignity and high yields.
- Goodajdar, Bijan Mombeni,Akbari, Farideh,Davarpanah, Jamal
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- MANUFACTURING METHOD OF AZIDO-TRIAZOLE COMPOUND AND PROPELLANT COMPOSITION FOR GAS GENERATOR
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The present invention relates to an azido-triazole compound producing method and a propellant composition for generating gas including an azido-triazole compound produced by the same. The azido-triazole compound producing method includes: a step of synthesizing a compound represented in chemical formula 1 into an azido compound represented in chemical formula 2; a step of synthesizing the azido compound into a cyclic triazole compound represented in chemical formula 4 by making the azido compound react with the compound represented in chemical formula 3; and a step of making the cyclic triazole compound react and synthesizing the same into the azido-triazole compound represented in chemical formula 5. The details of chemical formulas 1 to 5 are as defined in the specification. An azido-triazole compound produced by the present invention is not easily decomposed by acid and heat.COPYRIGHT KIPO 2019
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Paragraph 0035; 0130-0133
(2019/10/16)
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- Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles
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A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.
- Zhang, Dongsheng,Fan, Yingzhu,Yan, Zhongliang,Nie, Yi,Xiong, Xingquan,Gao, Lizhu
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supporting information
p. 4211 - 4216
(2019/08/07)
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- Dimeric palladium 1,2,3-triazol-5-ylidene complexes-synthesis, structure, reactivity and catalytic properties in Suzuki coupling
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New dimeric palladium 1,2,3-triazol-5-ylidene complexes of the general formula [{Pd(μ-Cl)Cl(tzNHC)}2] (tzNHC = 1-mesityl-3-methyl-4-phenyl-1H-1,2,3-triazol-5-ylidene; 1-hexyl-3-methyl-4-phenyl-1H-1,2,3-triazol-5-ylidene and 1-butyl-3-methyl-4-phenyl-1H-1,2,3-triazol-5-ylidene) were synthesized and characterized by spectroscopic methods, X-ray analysis and DFT calculations. For the mesityl substituted complex, the crystallographic structures of both the cisoidal and transoidal isomer were obtained. In the presence of an excess of 4-tolylboronic acid, the loss of the tzNHC ligand from the palladium coordination sphere as a 5-tolyltriazolium salt was observed. The complexes are precursors of palladium species catalytically active in the coupling of arylboronic acids with aryl bromides.
- Lorkowski, Jan,Zak, Patrycja,Kubicki, Maciej,Pietraszuk, Cezary,J?drzkiewicz, Dawid,Ejfler, Jolanta
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supporting information
p. 10134 - 10141
(2018/06/18)
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- Electron donor-free photoredox catalysis: Via an electron transfer cascade by cooperative organic photocatalysts
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Electron-donating sacrificial reagents are highly important for certain photo-redox reactions. However, the use of excessive amounts of sacrificial reagents, mostly amines, often leads to undesired side products and is especially troublesome for product purification. Herein, we take the light-induced electron transfer cascade process of natural photosystems as a role model and assemble organic photocatalysts into cooperative photocatalyst couples. The cooperative photocatalyst couples could undergo intermolecular electron transfer to facilitate the charge separation process and overcome the need for an extra electron donor. Time-resolved photoluminescence spectroscopy was conducted to precisely characterize the photo-excited dynamics within the cooperative photocatalyst couples. As a model photoredox reaction, the carbon-carbon formation reaction between heteroarenes and malonates, which usually requires electron-donating sacrificial reagents such as amines, was conducted to demonstrate the feasibility of the cooperative photocatalyst couples under visible light irradiation. A significant reaction conversion improvement from trace conversion for a single photocatalyst system to over 90% by cooperative photocatalyst couples was achieved.
- Wang, Lei,R?rich, Irina,Ramanan, Charusheela,Blom, Paul W. M.,Huang, Wei,Li, Run,Zhang, Kai A. I.
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p. 3539 - 3547
(2018/07/29)
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- Synthesis, characterization, and antimycobacterial activity of novel thymol-triazole hybrids
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Thymol is a naturally occurring phenolic compound showing various biological activities. A library of novel thymol-triazole hybrids was synthesized and evaluated for their inhibitory activity against Mycobacterium tuberculosis (M.tb), the causative agent of TB. Most of the compounds were found to be active against M.tb H37Rv at 50 μg/mL concentration. These identified compounds have promise to be further optimized into more potent inhibitors against M.tb.
- Negi, Beena,Rawat, Diwan S
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p. 113 - 124
(2018/09/14)
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- Remarkably improved stability and enhanced activity of a: Burkholderia cepacia lipase by coating with a triazolium alkyl-PEG sulfate ionic liquid
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Three types of triazolium cetyl-PEG10 sulfate ionic liquid were synthesized and their activation of Burkholderia cepacia lipase was investigated; both the reaction rate and enantioselectivity depended on the cationic part of the coating ILs and 1-butyl-3-methyl-1,2,3-triazolium cetyl-PEG10 sulfate (Tz1)-coated lipase PS, which is especially suitable for the transesterification of 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, and 1-(pyridin-4-yl)ethanol, among 12 types of tested secondary alcohol. The most important result was obtained when these enzymes were stored in an IL ([N221MEM][Tf2N]) solvent: Tz1-PS showed an amazing stability and it exhibited an excellent activity after 2 years when the enzyme was stored in [N221MEM][Tf2N].
- Nishihara,Shiomi,Kadotani,Nokami,Itoh
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supporting information
p. 5250 - 5256
(2017/11/09)
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- COPOLYMERS OF FORMULA (I) AND USES
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Disclosed is a copolymer of following formula (I): in which:—x is an integer between 10 and 250, preferably between 40 and 120, —y is an integer between 4 and 100, preferably between 10 and 100, preferably between 19 and 60, —z is an integer between 0 and
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Paragraph 0110-0112
(2017/04/11)
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- Introducing the 4-Phenyl-1,2,3-Triazole Moiety as a Versatile Scaffold for the Development of Cytotoxic Ruthenium(II) and Osmium(II) Arene Cyclometalates
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Herein we report the synthesis, anticancer potency in vitro, biomolecule interaction, and preliminary mode of action studies of a series of cyclometalated 1,2,3-triazole-derived ruthenium(II) (2a-e) and osmium(II) (3a-e) organometallics of the general for
- Riedl, Christoph A.,Flocke, Lea S.,Hejl, Michaela,Roller, Alexander,Klose, Matthias H. M.,Jakupec, Michael A.,Kandioller, Wolfgang,Keppler, Bernhard K.
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supporting information
p. 528 - 541
(2017/01/13)
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- Effect of 1,2,3-triazole salts, non-classical bioisosteres of miltefosine, on Leishmania amazonensis
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Here, we report the effect of new non-classical bioisosteres of miltefosine on Leishmania amazonensis. Fifteen compounds were synthesized and the compound dhmtAc, containing an acetate anion, a side chain of 10 carbon atoms linked to N-1 and a methyl group linked to N-3, showed high and selective biological activity against L. amazonensis. On the intracellular amastigotes, stages of the parasite related to human disease, the IC50 values were near or similar to the 1.0?μM (0.9, 0.8 and 1.0?μM on L. amazonensis-WT, and two transgenic L. amazonensis expressing GFP and RFP, respectively), being more active than miltefosine. Furthermore, dhmtAc did not show toxic effects on human erythrocytes and macrophages (CC50?=?115.9?μM) being more destructive to the intracellular parasites (selectivity index?>?115). Promastigotes and intramacrophage amastigotes treated with dhmtAc showed low capacity for reversion of the effect of the compound. A study of the mechanism of action of this compound showed some features of metazoan apoptosis, including cell volume decreases, loss of mitochondrial membrane potential, ROS production, an increase in the intracellular lipid bodies, in situ labeling of DNA fragments by TUNEL labeling and phosphatidylserine exposure to the outerleaflet of the plasma membrane. In addition, the plasma membrane disruption, revealed by PI labeling, suggests cell death by necrosis. No increase in autophagic vacuoles formation in treated promastigotes was observed. Taken together, the data indicate that the bioisostere of miltefosine, dhmtAc, has promising antileishmanial activity that is mediated via apoptosis and necrosis.
- Stroppa, Pedro H.F.,Antinarelli, Luciana M.R.,Carmo, Arturene M.L.,Gameiro, Jacy,Coimbra, Elaine S.,da Silva, Adilson D.
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p. 3034 - 3045
(2017/05/29)
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- Synthesis and antiproliferative activity of new 1,2,3-triazole/flavone hybrid heterocycles against human cancer cell lines
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A series of new 1,2,3-triazole/flavone hybrid heterocycles were synthesized from 6-amino flavone via key intermediate N-propargyl flavone 6 by adopting the Sharpless Click reaction. Copper(I) catalyzed 1,3-dipolar cycloaddition reaction that gave products in high yields. All the synthesized compounds were screened for their in vitro antiproliferative activity against four human cancer cell lines, HeLa (cervical cancer cell line), MIA PaCa (pancreatic cancer cell line), MDA-MB-231 (breast cancer cell line), and IMR 32 (neuroblastoma cancer cell line). Compounds 7a, 7b, 7d, 7g (GI50 = 0.01–0.68 μM) demonstrated promising antiproliferative activity.
- Sowjanya,Jayaprakash Rao,Murthy
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p. 1864 - 1871
(2017/09/25)
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- Hydrotrope promoted in situ azidonation followed by copper catalyzed regioselective synthesis of β-hydroxytriazoles
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Abstract: The rapid method for the synthesis of organic azides was achieved by employing azide acceptors such as halides, epoxides and pseudohalides like diazonium salts and aryl boronic acids in hydrotropic media. In extension, the sequential multicomponent reaction of epoxides, azide and alkynes using copper catalysis has been discussed. The reaction proceeds via the in situ generation of azido-alcohol followed by synthesis of chiral β-hydroxytriazoles. This [3?+?2] cycloaddition reaction of azide and alkyne using copper catalysis serves as a green and efficient protocol in “Click Chemistry”. The nucleophilic addition of azide to epoxide and alkyne-azide cycloaddition is the two simultaneous regioselective click reactions observed in the proposed method. Graphical Abstract: [Figure not available: see fulltext.].
- Patil, Amol,Salunkhe, Rajashri
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p. 4175 - 4187
(2017/06/20)
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- Synthesis of α-santonin derived acetyl santonous acid triazole derivatives and their bioevaluation for T and B-cell proliferation
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A new series of α-santonin derived acetyl santonous acid 1,2,3-triazole derivatives were synthesised using Huisgen 1,3-dipolar cyclo-addition reaction (click chemistry approach) and evaluated for their in vitro inhibition activity on concanavalin A (ConA) induced T cell proliferation and lipopolysaccharide (LPS) induced B cell proliferation. Among the synthesised series, compounds 2-10 and 19 exhibited significant inhibition against ConA and LPS stimulated T-cell and B-cell proliferation in a dose dependent manner. More significantly compounds 4, 9-10 and 19 exhibited potent inhibition activity with remarkably lower cytotoxicity on the mitogen-induced T cell and B cell proliferation at 1 μM concentration. The compound 6 displayed potent immunosuppressive effects with ~89% against LPS induced B-cell and ~83% against ConA stimulated T-cell proliferation at 100 μM concentration without cytotoxicity. Compound 10 was more selective against B cell proliferation and exhibited 81% and 69% suppression at 100 and 1 μM concentration respectively. The present study led to the identification of several santonin analogs with reduced cytotoxicity and strong inhibition activity against the cell proliferation induced by the mitogens.
- Dangroo, Nisar A.,Singh, Jasvinder,Dar, Alamgir A.,Gupta, Nidhi,Chinthakindi, Praveen K.,Kaul, Anpurna,Khuroo, Mohmmed A.,Sangwan, Payare L.
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p. 160 - 169
(2016/05/24)
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- Application of magnetic dicationic ionic liquid phase transfer catalyst in nuclophilic substitution ractions of benzyl halides in water
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Magnetic dicationic ionic liquid (MDIL) was successfully prepared and evaluated as phase-transfer catalyst for nucleophilic substitution reactions. The reactions was occurred in water and furnished the corresponding benzyl derivatives in high yields. No evidence for the formation of by-product for example benzyl alcohol of the reaction was observed and the products were obtained in pure form without further purification.
- Aghajeri, Manouchehr,Kiasat, Ali Reza,Goodajdar, Bijan Mombeni
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p. 1691 - 1695
(2016/08/06)
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- 1-Alkyl-3-methyl-1,2,3-triazolium [NTf2] ionic liquids: synthesis and properties
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A series of 1-alkyl-3-methyl-1,2,3-triazolium bis(trifluoromethylsulfonyl)imide [NTf2] ionic liquids were prepared synthetically using azide-alkyne 'click' cyclization chemistry and their physicochemical and thermal properties were determined. Increasing the alkyl chain length resulted in increased viscosities and higher thermal transitions (Tg or Tm) with depressed molar conductivities. Walden plot analysis indicated that the ionicity of 1-butyl-3-methyl-1,2,3-triazolium [NTf2] was comparable to the analogous imidazolium system and higher than the 1,2,4-triazolium equivalent.
- Reeder, Zachary K.,Adler, Abigail M.,Miller, Kevin M.
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p. 206 - 209
(2015/12/30)
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- An efficient synthesis of phosphoramidates from halides in aqueous ethanol
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An environment friendly and efficient synthesis of primary phosphoramidates has been developed from benzyl/allyl/alkyl/propargyl halides in aqueous ethanol as a green reaction medium via in-situ formation of azide. The method is simple, metal free and high yielding at room temperature with wide substrate scope and functional group compatibility. The optimized protocol can be used for synthesis of phosphoramidate intermediates used as prodrug moieties to improve therapeutic potential of the parent drug.
- Dangroo,Dar,Shankar,Khuroo,Sangwan
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p. 2717 - 2722
(2016/06/09)
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- Cd(II)-MOF-IM: Post-synthesis functionalization of a Cd(II)-MOF as a triphase transfer catalyst
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A robust and porous Cd(ii)-MOF based on a bent imidazole-bridged ligand was synthesized and post-synthetically functionalized with linear alkyl chains to afford imidazolium salt (IM)-type triphase transfer catalysts for organic transformations. The imidazolium salt decorated Cd(ii)-MOF-IM exhibits typical solid phase transfer catalytic behavior for the azidation and thiolation of bromoalkane between aqueous/organic phases. Moreover, they can be easily recovered and reused under the PTC conditions. Cd(ii)-MOF-IM herein created a versatile family of solid phase transfer catalysts for promoting a broad scope of reactions carried out in a biphasic mixture of two immiscible solvents.
- Wang, Jian-Cheng,Ma, Jian-Ping,Liu, Qi-Kui,Hu, Yu-Hong,Dong, Yu-Bin
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supporting information
p. 6989 - 6992
(2016/06/09)
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- Triazole substitution of a labile amide bond stabilizes pantothenamides and improves their antiplasmodial potency
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The biosynthesis of coenzyme A (CoA) from pantothenate and the utilization of CoA in essential biochemical pathways represent promising antimalarial drug targets. Pantothenamides, amide derivatives of pantothenate, have potential as antimalarials, but a serum enzyme called pantetheinase degrades pantothenamides, rendering them inactive in vivo. In this study, we characterize a series of 19 compounds that mimic pantothenamides with a stable triazole group instead of the labile amide. Two of these pantothenamides are active against the intraerythrocytic stage parasite with 50% inhibitory concentrations (IC50s) of ~50 nM, and three others have submicromolar IC50s. We show that the compounds target CoA biosynthesis and/or utilization. We investigated one of the compounds for its ability to interact with the Plasmodium falciparum pantothenate kinase, the first enzyme involved in the conversion of pantothenate to CoA, and show that the compound inhibits the phosphorylation of [14C]pantothenate by the P. falciparum pantothenate kinase, but the inhibition does not correlate with antiplasmodial activity. Furthermore, the compounds are not toxic to human cells and, importantly, are not degraded by pantetheinase.
- Howieson, Vanessa M.,Tran, Elisa,Hoegl, Annabelle,Fam, Han Ling,Fu, Jonathan,Sivonen, Kate,Li, Xiao Xuan,Auclair, Karine,Saliba, Kevin J.
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p. 7146 - 7152
(2016/11/28)
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- Preparation of novel magnetic dicationic ionic liquid polymeric phase transfer catalyst and their application in nucleophilic substitution reactions of benzyl halides in water
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PEG-based magnetic dicationic ionic liquid was successfully prepared and evaluated as phase-transfer catalyst for nucleophilic substitution reactions of benzyl halides for the synthesis of benzyl azides and cyanides from good to excellent yields at 90 °C in water. The reactions occur in water and furnish the corresponding benzyl derivatives in high yields. No evidence for the formation of by-product for example benzyl alcohol of the reaction was observed and the products were obtained in pure form without further purification.
- Godajdar, Bijan Mombani,Ansari, Bita
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- A copper(II)-thioamide combination as a robust heterogeneous catalytic system for green synthesis of 1,4-disubstituted-1,2,3-triazoles under click conditions
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An efficient and practical synthesis of 1,4-disubstituted-1,2,3-triazoles under click conditions using a copper(ii)-thioamide combination as an efficient heterogeneous catalyst is disclosed. Mild reaction conditions and high yields make this method an attractive option for the preparation of triazole derivatives. The key to this procedure was the generation of Cu(I) required for the azide-alkyne cycloaddition, which was achieved by in situ reduction of Cu(II) using thiobenzanilide as reduction agent and ligand.
- Mirjafary, Zohreh,Ahmadi, Leila,Moradi, Masomeh,Saeidian, Hamid
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p. 78038 - 78046
(2015/09/28)
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- Synthesis of new hybrid heterocyclic compounds having 1,2,3-triazole and isoxazole via click chemistry
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A simple and highly efficient method for the regioselective synthesis of isoxazolyl-1,4-disubstituted-1,2,3-triazoles 6a-l in good to excellent yields from terminal alkynes having isoxazole scaffold 4a-c and various azides through Cu(I)-catalyzed 1,3-dipolar cycloaddition is described. The reaction proceeds smoothly in 1:1 mixture of t-BuOH and water at RT. The structures of all newly synthesized hybrid heterocycles are established on the basis of spectral data ir, 1H nmr, mass, and elemental analysis.
- Jayaprakash Rao,Srinivas
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p. 1675 - 1678
(2015/01/09)
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- CURCUMIN ANALOGS AND METHODS OF MAKING AND USING THEREOF
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Compounds having Formula I or II, and methods of making and using thereof, are described herein:
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Page/Page column 76
(2014/02/16)
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- 1,2,3-Triazole-derived naphthalimides as a novel type of potential antimicrobial agents: Synthesis, antimicrobial activity, interaction with calf thymus DNA and human serum albumin
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A series of 1,2,3-triazole-derived naphthalimides as a novel type of potential antimicrobial agents were synthesized and characterized by IR, NMR and HRMS spectra. All the new compounds were screened for their antimicrobial activity against four Gram-positive bacteria, four Gram-negative bacteria and three fungi. Bioactive assay manifested that 3,4-dichlorobenzyl compound 9e and its corresponding hydrochloride 11e showed better anti-Escherichia coli activity than Norfloxacin and Chloromycin. Preliminary research revealed that compound 9e could effectively intercalate into calf thymus DNA to form compound 9e-DNA complex which might block DNA replication and thus exert antimicrobial activities. Human serum albumin could effectively store and carry compound 9e by electrostatic interaction.
- Lv, Jing-Song,Peng, Xin-Mei,Kishore, Baathulaa,Zhou, Cheng-He
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p. 308 - 313
(2014/01/17)
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- Synthesis of novel 1,2,3-triazole derivatives of isoniazid and their in vitro and in vivo antimycobacterial activity evaluation
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We report herein the synthesis and antimycobacterial activity of 1,2,3-triazole derivatives of isoniazid. Most of the compounds exhibited potent activity against Mycobacterium tuberculosis H37Rv strain with MIC99 values ranging from 0.195 to 1.
- Kumar, Deepak,Beena,Khare, Garima,Kidwai, Saqib,Tyagi, Anil K.,Singh, Ramandeep,Rawat, Diwan S.
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p. 301 - 313
(2014/06/09)
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- Asymmetrical azobenzene liquid crystals with high birefringence prepared via click chemistry
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Asymmetrical azobenzene liquid crystals with high birefringence were prepared via the click chemistry method. The chemical structures of the synthetic intermediates and compounds were confirmed by FT-IR and 1H-NMR. The liquid crystal behavior,
- Miao, Zongcheng,Zhang, Yongming,Zhao, Yuzhen,Wang, Zhixue,Wang, Dong
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- Immobilization of a N-substituted azaphosphatrane in nanopores of SBA-15 silica for the production of cyclic carbonates
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A novel N-substituted azaphosphatrane molecular precursor bearing an alkyne tether was synthesized using a multi-step strategy and covalently immobilized onto SBA-15 type silica through triazole linkages by means of the well-known click chemistry. The resulting hybrid material, [7]@SBA-15, was characterized well by methods appropriate to molecular species (e.g. solid state 13C, 31P and 29Si NMR, infrared spectroscopy and elemental analysis) as well as techniques more commonly associated with the characterization of mesoporous solids (nitrogen sorption isotherms, powder X-ray diffraction, TGA analysis). The catalytic activity of [7]@SBA-15 was then evaluated in the coupling of CO2 with two epoxides (styrene oxide and epichlorohydrin) and compared to its monotriazole modified AZAP molecular analog, 8. This work represents the first example of silica modified N-substituted azaphosphatrane for the production of cyclic carbonates. This journal is the Partner Organisations 2014.
- Chatelet, Bastien,Joucla, Lionel,Dutasta, Jean-Pierre,Martinez, Alexandre,Dufaud, Veronique
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p. 14164 - 14172
(2014/08/18)
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- Novel 1,3-alternate thiacalix[4]arenes: Click synthesis, silver ion binding and self-assembly
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A series of novel 1,3-alternate thiacalixarene derivatives containing triazole groups were synthesized directly from a conformationally mixed intermediate in high yields using click chemistry. They were used as building blocks for supramolecular self-assembly architecture, and shown to be good Ag+ receptors. As confirmed by AFM, one of the compounds was found to form nanorod aggregates by silver ion binding. The Royal Society of Chemistry 2013.
- Zhao, Haiyang,Zhan, Junyan,Zou, Zhilong,Miao, Fajun,Chen, Hong,Zhang, Li,Cao, Xianliang,Tian, Deimei,Li, Haibing
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p. 1029 - 1032
(2013/03/28)
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- Facet-dependent catalytic activity of Cu2O nanocrystals in the one-pot synthesis of 1,2,3-triazoles by multicomponent click reactions
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We report the highly facet-dependent catalytic activity of Cu2O nanocubes, octahedra, and rhombic dodecahedra for the multicomponent direct synthesis of 1,2,3-triazoles from the reaction of alkynes, organic halides, and NaN3. The catalytic activities of clean surfactant-removed Cu 2O nanocrystals with the same total surface area were compared. Rhombic dodecahedral Cu2O nanocrystals bounded by {110} facets were much more catalytically active than Cu2O octahedra exposing {111} facets, whereas Cu2O nanocubes displayed the slowest catalytic activity. The superior catalytic activity of Cu2O rhombic dodecahedra is attributed to the fully exposed surface Cu atoms on the {110} facet. A large series of 1,4-disubstituted 1,2,3-triazoles have been synthesized in excellent yields with high regioselectivity under green conditions by using these rhombic dodecahedral Cu2O catalysts, including the synthesis of rufinamide, an antiepileptic drug, demonstrating the potential of these nanocrystals as promising heterogeneous catalysts for other important coupling reactions.
- Chanda, Kaushik,Rej, Sourav,Huang, Michael H.
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p. 16036 - 16043
(2014/04/03)
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- Facile and exclusive formation of aziridinofullerenes by acid-catalyzed denitrogenation of triazolinofullerenes
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Variously substituted [6,6]closed aziridinofullerenes were exclusively obtained from acid-catalyzed denitrogenation of triazolinofullerenes without formation of relevant [5,6]open azafulleroids, which are the major products on noncatalyzed denitrogenation
- Ikuma, Naohiko,Mikie, Tsubasa,Doi, Yuta,Nakagawa, Koji,Kokubo, Ken,Oshima, Takumi
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supporting information
p. 6040 - 6043
(2013/02/23)
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- Cobalt complexes with click-derived functional tripodal ligands: Spin crossover and coordination ambivalence
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We demonstrate the use of a Cu(I) catalyzed "Click" reaction in the synthesis of novel ligands for spin crossover complexes. The reaction between azides and alkynes was used to synthesize the reported tripodal ligand tris[(1-benzyl-1H-1,2,3-triazol-4-yl)m
- Schweinfurth, David,Weisser, Fritz,Bubrin, Denis,Bogani, Lapo,Sarkar, Biprajit
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experimental part
p. 6114 - 6121
(2011/08/22)
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- Ionic liquid brush as a highly efficient and reusable catalyst for on-water nucleophilic substitutions
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A very efficient and reusable catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields. The reaction proceeds smoothly and cleanly without any organic cosolvent or other adductive, and the brush can be reused at least 10 times without noticeable loss of the catalytic activity. The high efficiency, simplicity of product and catalyst isolation, outstanding recyclability, and organic-solvent-free conditions show promise for the use of this catalyst in the laboratory and in industry. A highly efficient and reusable ionic liquid brush catalyst has been developed for the on-water nucleophilic substitution of alkyl halides and tosylates with azide or thiocyanate in excellent to quantitative yields without any organic cosolvent or other adductive. The catalyst can be reused at least 10 times without noticeable loss of the catalytic activity. Copyright
- Li, Jing,Cao, Jing-Jing,Wei, Jun-Fa,Shi, Xian-Ying,Zhang, Li-Hui,Feng, Jin-Juan,Chen, Zhan-Guo
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supporting information; experimental part
p. 229 - 233
(2011/03/20)
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- Chemical modification of poly(vinylacetylene) and synthesis of poly(1,2,3-triazole)s
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A series of new polymers containing 1,2,3-triazoles were synthesized and their structures and properties were characterized by FT-IR, 1H NMR, TGA, DSC and GPC. The results showed that the polymers modified by alkyl groups had good solubility, thermal stability and reasonable molecular weights. It was also demonstrated that the properties of fluorine-containing polymers were seriously affected by fluorine atoms with hydrophobic and chemical proof properties.
- Wang, Lian-Jun,Liao, Shan,Wang, Le-Yong
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experimental part
p. 1471 - 1474
(2011/12/15)
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- Copper(I)-catalyzed cycloaddition of methyl O-propargylpodocarpate and azides at room temperature
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Copper iodide was employed as an efficient catalyst for the synthesis of 1,2,3-triazole derivatives of podocarpic acid at room temperature through "click" chemistry cycloaddition reactions of methyl O-propargylpodocarpate and propargyl O-propargylpodocarpate with azides.
- Nguyen, Dao M.,Miles, D. Howard
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experimental part
p. 1759 - 1771
(2011/06/24)
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- Tridentate cyclometalated ruthenium(II) complexes of "click" ligand 1,3-Di(1,2,3-triazol-4-yl)benzene
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A tridentate cyclometalating ligand, 1,3-di(1,2,3-triazol-4-yl)benzene (dtab), has been prepared and used for the syntheses of a number of cyclometalated RuII complexes. A comparison of the electrochemical and spectroscopic properties of cyclometalated complexes made from dtab or 1,3-di(2-pyridyl)benzene is presented as well.
- Yang, Wen-Wen,Wang, Lei,Zhong, Yu-Wu,Yao, Jiannian
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experimental part
p. 2236 - 2240
(2011/06/22)
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- Bicyclic 1,2,3-triazolium ionic liquids: Synthesis, characterization, and application to rutaecarpine synthesis
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Starting with commercial reagents, bicyclic 1,2,3-triazolium ionic liquids [b-3C-tr][NTf2] (1) and [b-4C-tr][NTf2] (2) were synthesized in four steps with high overall isolated yields of 68% and 76%, respectively. Since the C-5 hydrogen is acidic, under basic condition ionic liquids 1 and 2 were readily methylated with methyl iodide to afford chemically stable ionic liquids 7 and 8 at room temperature (88% and 82%, respectively). Ionic liquid 1 was used as the ionic solvent to demonstrate its usefulness for the synthesis of rutaecarpine, a natural product.
- Tseng, Ming-Chung,Cheng, Hui-Ting,Shen, Meng-Jane,Chu, Yen-Ho
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supporting information; experimental part
p. 4434 - 4437
(2011/10/05)
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- Bivalent dopamine D2 receptor ligands: Synthesis and binding properties
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Dopamine D2 receptor homodimers might be of particular importance in the pathophysiology of schizophrenia and, thus, serve as promising target proteins for the discovery of atypical antipsychotics. A highly attractive approach to investigate and control GPCR dimerization may be provided by the exploration and characterization of bivalent ligands, which can act as molecular probes simultaneously binding two adjacent binding sites of a dimer. The synthesis of bivalent dopamine D2 receptor ligands of type 1 is presented, incorporating the privileged structure of 1,4-disubstituted aromatic piperidines/piperazines (1,4-DAPs) and triazolyl-linked spacer elements. Radioligand binding studies provided diagnostic insights when Hill slopes close to two for bivalent ligands with particular spacer lengths and a comparative analysis with respective monovalent control ligands and unsymmetrically substituted analogues indicated a bivalent binding mode with a simultaneous occupancy of two neighboring binding sites.
- Kühhorn, Julia,Hübner, Harald,Gmeiner, Peter
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supporting information; experimental part
p. 4896 - 4903
(2011/09/19)
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- Development of a bivalent dopamine D2 receptor agonist
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Bivalent D2 agonists may function as useful molecular probes for the discovery of novel neurological therapeutics. On the basis of our recently developed bivalent dopamine D2 receptor antagonists of type 1, the bivalent agonist 2 was
- Kühhorn, Julia,G?tz, Angela,Hübner, Harald,Thompson, Dawn,Whistler, Jennifer,Gmeiner, Peter
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supporting information; experimental part
p. 7911 - 7919
(2012/01/05)
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- Synthesis of novel 1,4-disubstituted-1,2,3-triazole semi synthetic analogues of forskolin by click reaction
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New 1,4-disubstituted-1,2,3-triazole analogues of forskolin (5a-g, 6a-g) have been prepared by regioselective propargylation at 1-position followed by Cu(I) catalysed cycloaddition of different alkyl azides under the click reaction conditions. An interesting acyl shift in the base catalysed propargylation afforded a new series of 1,4-disubstituted-1,2,3-triazole analogues of forskolin (6a-g). These analogues have potential selective therapeutic applications as antihypertensive, antiglaucoma, antiasthma and antiobesity agents.
- Koteswara Reddy,Santosh Kumar,Sreenivas,David Krupadanam,Janardhan Reddy
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body text
p. 6537 - 6540
(2012/01/06)
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- Click assembly of dye-functionalized octasilsesquioxanes for highly efficient and photostable photonic systems
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New hybrid organic-inorganic dyes based on an azide-functionalized cubic octasilsesquioxane (POSS) as the inorganic part and a 4,4-difluoro-4-bora-3a,4a- diaza-s-indacene (BDP) chromophore as the organic component have been synthesized by copper(I)-cataly
- Perez-Ojeda, M. Eugenia,Trastoy, Beatriz,Lopez-Arbeloa, Inigo,Banuelos, Jorge,Costela, Ungel,Garcia-Moreno, Inmaculada,Chiara, Jose Luis
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experimental part
p. 13258 - 13268
(2012/02/14)
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- Selective fluorescence sensing of zinc and mercury ions with hydrophilic 1,2,3-triazolyl fluorene probes
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The ability to rapidly detect biologically and environmentally significant metal ions such as zinc and mercury is important to study a number of important cellular and environmental processes. Hydrophilic bis(1,2,3-triazolyl)fluorene- based derivatives containing a 1,2,3-triazole-based recognition moiety were synthesized through Click chemistry and characterized by UV-vis absorption, fluorescence emission, and two-photon absorption as new fluorescence sensing probes, selective for Zn2+ and Hg2+ ions. The UV-vis absorption and fluorescence emission spectra of the complexes exhibited blue-shifted absorption and emission spectra upon chelation to Zn2+ and Hg2+ ions, resulting in ca. 2-fold enhancement in fluorescence. Fluorometric titration revealed that 1:2 and 1:3 ligand to metal complexes formed with binding constants of 108 and 1016 for Zn 2+ and Hg2+, respectively. The two-photon absorption cross sections for the probes and probe-metal ion complexes ranged from 200 to 350 GM at 800 nm. These novel fluorescent compounds may have potential as new metal ion sensors to probe cellular and biological environments.
- Nguyen, Dao M.,Frazer, Andrew,Rodriguez, Luis,Belfield, Kevin D.
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experimental part
p. 3472 - 3481
(2011/12/03)
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- Highly active copper-catalysts for azide-alkyne cycloaddition
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Bis-triphenylphosphano complexes of copper(i)-carboxylates serve as efficient catalysts for azide-alkyne cycloaddition. The triazole formation takes place straightforwardly at ambient temperature providing a wide variety of products with good yields in th
- Gonda, Zsombor,Novak, Zoltan
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supporting information; experimental part
p. 726 - 729
(2010/04/25)
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- Synthesis, antioxidant and antimicrobial activity of novel benzene-1,4-diamine-bis-dioxaphosphepine-6λ5 iminophosphoranes
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(Chemical Equation Presented). A new class of novel benzene-1,4-diamine- bis-dioxaphosphepine-6λ5 iminophosphoranes (5a-j) were synthesized by the reaction of 6-chlorodibenzo[d,f][1,3,2]dioxaphosphepine (2) with 1,4-diaminobenzene to form bis-dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl- benzene-diamine (3). Its subsequent reaction with different alkyl/aryl azides (4a-j) in tetrahydrofuran at 50-60°C under inert atmosphere yielded title compounds. Their structures were established by elemental analysis, IR, 1H, 13C, 31P NMR, and mass spectral studies. All the title compounds were screened for antioxidant properties and found to exhibit potent in vitro antioxidant and antimicrobial activity.
- Veera Narayana Reddy,Chandra Sekhar Reddy,Suresh Kumar,Suresh Reddy,Naga Raju
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experimental part
p. 538 - 542
(2010/09/05)
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- Click chemistry approach to new N-substituted aminocyclitols as potential pharmacological chaperones for gaucher disease
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New N-alkylaminocyclitols bearing a 1,2,3-triazole system at different positions of the alkyl chain have been prepared as potential GCase pharmacological chaperones using click chemistry approaches. Among them, compounds 1d and 1e, with the shorter spacer
- Díaz, Lucía,Bujons, Jordi,Casas, Josefina,Llebaria, Amadeu,Delgado, Antonio
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supporting information; experimental part
p. 5248 - 5255
(2010/10/19)
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