- Chemoselective triazole-phosphonamidate conjugates suitable for photorelease
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Herein, we describe a new method for the conjugation of azide-containing target compounds that can be readily released as amines by irradiation with near UV light. This concept is based on a two-step protocol employing the chemoselective CuAAC and Staudinger-phosphonite reactions to deliver photo-cleavable phosphonamidate conjugates in high yields starting from 2-nitrobenzyl substituted phosphonites.
- Siebertz, Kristina D.,Hackenberger, Christian P. R.
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Read Online
- Small-Molecule Kinase-Inhibitors-Loaded Boron Cluster as Hybrid Agents for Glioma-Cell-Targeting Therapy
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The reported new anilinoquinazoline-icosahedral borane hybrids have been evaluated as glioma targeting for potential use in cancer therapy. Their anti-glioma activity depends on hybrids’ lipophilicity; the most powerful compound against glioma cells, a 1,
- Couto, Marcos,Mastandrea, Ignacio,Cabrera, Mauricio,Cabral, Pablo,Teixidor, Francesc,Cerecetto, Hugo,Vi?as, Clara
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Read Online
- Interrupted CuAAC-Thiolation for the Construction of 1,2,3-Triazole-Fused Eight-Membered Heterocycles from O-/N-Propargyl derived Benzyl Thiosulfonates with Organic Azides
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A copper(I)-catalyzed interrupted click-sulfenylation of O-/N-propargyl benzyl thiosulfonates with organic azides has been disclosed. The unified CuAAC-thiolation provides a wide range of triazole-fused eight-membered heterocycles in good to high (51–94%) yields under mild reaction conditions. Moreover, a three-component reaction is also achieved involving O-/N-propargyl benzyl thiosulfonates, benzyl bromide, and sodium azide to deliver fused-triazoles in 61–74% yields. From a synthetic point of view, the present protocol has been demonstrated at gram-scale reactions. A plausible mechanism is also proposed based on experimental results and control experiments. (Figure presented.).
- Jannapu Reddy, Raju,Waheed, Md.,Haritha Kumari, Arram,Rama Krishna, Gamidi
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supporting information
p. 319 - 325
(2021/12/02)
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- One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride
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Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.
- Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.
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p. 3768 - 3777
(2021/03/01)
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- Iridium-catalyzed orthogonal and regioselective synthesis of triazole disulfides in aqueous media under mild conditions
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An orthogonal and regioselective synthesis of triazole disulfides in aqueous media under mild conditions has been developed. This simple and practical approach is environment-friendly and compatible with oxygen/water and various complex biological media.
- Li, Junhao,Li, Ming,Song, Wangze,Zheng, Nan,Zheng, Yubin
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supporting information
p. 2394 - 2398
(2020/05/13)
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- Synthesis and spectral properties of 6′-triazolyl-dihydroxanthene-hemicyanine fused near-infrared dyes
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We describe the synthesis of a range of 6′-triazolyl-dihydroxanthene-hemicyanine (DHX-hemicyanine) fused dyes through an effective copper-catalyzed azide-alkyne cycloaddition (CuAAC) "click"reaction, with the aim of providing molecular diversity and evaluating the spectral properties of these near-infrared (NIR)-active materials. This was implemented by reacting 15 different aliphatic and aromatic azides with a terminal alkynyl-based DHX-hemicyanine hybrid scaffold prepared in four steps and 35% overall yield from 4-bromosalicylaldehyde. The resulting triazole derivatives have been fully characterized and their optical properties determined both in organic solvents and under simulated physiological conditions (phosphate buffered saline containing 5% of bovine serum albumin protein). This systematic study is a first important step towards the development of NIR-I fluorogenic "click-on"dyes or related photoactive agents for light-based diagnostic and/or therapeutic applications.
- Gu, Lingyue,Renault, Kévin,Romieu, Anthony,Richard, Jean-Alexandre,Srinivasan, Rajavel
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supporting information
p. 12208 - 12215
(2020/07/30)
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- A click-based modular approach to introduction of peroxides onto molecules and nanostructures
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Copper-promoted azide/alkyne cycloadditions (CuAAC) are explored as a tool for modular introduction of peroxides onto molecules and nanomaterials. Dialkyl peroxide-substituted alkynes undergo Cu(i)-promoted reaction with azides in either organic or biphas
- Dussault, Patrick H.,Horn, Alissa
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p. 44408 - 44429
(2020/12/28)
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- ENVIRONMENTALLY-FRIENDLY HYDROAZIDATION OF OLEFINS
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The present invention provides processes for the synthesis of organic azides, intermediates for the production thereof, and compositions related thereto.
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Page/Page column 63; 67-68; 71
(2020/01/24)
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- Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins
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We herein report a direct intermolecular anti-Markovnikov hydroazidation method for unactivated olefins, which is promoted by a catalytic amount of bench-stable benziodoxole at ambient temperature. This method facilitates previously difficult, direct addition of hydrazoic acid across a wide variety of unactivated olefins in both complex molecules and unfunctionalized commodity chemicals. It conveniently fills a synthetic chemistry gap of existing olefin hydroazidation procedures, and thereby provides a valuable tool for azido-group labeling in organic synthesis and chemical biology studies.
- Li, Hongze,Shen, Shou-Jie,Zhu, Cheng-Liang,Xu, Hao
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supporting information
p. 9415 - 9421
(2019/06/21)
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- Design, biological evaluation and X-ray crystallography of nanomolar multifunctional ligands targeting simultaneously acetylcholinesterase and glycogen synthase kinase-3
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Both cholinesterases (AChE and BChE) and kinases, such as GSK-3α/β, are associated with the pathology of Alzheimer's disease. Two scaffolds, targeting AChE (tacrine) and GSK-3α/β (valmerin) simultaneously, were assembled, using copper(I)-catalysed azide alkyne cycloaddition (CuAAC), to generate a new series of multifunctional ligands. A series of eight multi-target directed ligands (MTDLs) was synthesized and evaluated in vitro and in cell cultures. Molecular docking studies, together with the crystal structures of three MTDL/TcAChE complexes, with three tacrine-valmerin hybrids allowed designing an appropriate linker containing a 1,2,3-triazole moiety whose incorporation preserved, and even increased, the original inhibitory potencies of the two selected pharmacophores toward the two targets. Most of the new derivatives exhibited nanomolar affinity for both targets, and the most potent compound of the series displayed inhibitory potencies of 9.5 nM for human acetylcholinesterase (hAChE) and 7 nM for GSK-3α/β. These novel dual MTDLs may serve as suitable leads for further development, since, in the micromolar range, they exhibited low cytotoxicity on a panel of representative human cell lines including the human neuroblastoma cell line SH-SY5Y. Moreover, these tacrine-valmerin hybrids displayed a good ability to penetrate the blood-brain barrier (BBB) without interacting with efflux pumps such as P-gp.
- Oukoloff, Killian,Coquelle, Nicolas,Bartolini, Manuela,Naldi, Marina,Le Guevel, Rémy,Bach, Stéphane,Josselin, Béatrice,Ruchaud, Sandrine,Catto, Marco,Pisani, Leonardo,Denora, Nunzio,Iacobazzi, Rosa Maria,Silman, Israel,Sussman, Joel L.,Buron, Frédéric,Colletier, Jacques-Philippe,Jean, Ludovic,Routier, Sylvain,Renard, Pierre-Yves
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- Identification of highly potent and selective Cdc25 protein phosphatases inhibitors from miniaturization click-chemistry-based combinatorial libraries
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Cell division cycle 25 (Cdc25) protein phosphatases play key roles in the transition between the cell cycle phases and their association with various cancers has been widely proven, which makes them ideal targets for anti-cancer treatment. Though several Cdc25 inhibitors have been developed, most of them displayed low activity and poor subtype selectivity. Therefore, it is extremely important to discover novel small molecule inhibitors with potent activities and significant selectivity for Cdc25 subtypes, not only served as drugs to treat cancer but also to probe its mechanism in transitions. In this study, miniaturized parallel click chemistry synthesis via CuAAC reaction followed by in situ biological screening were used to discover selective Cdc25 inhibitors. The bioassay results showed that compound M2N12 proved to be the most potent Cdc25 inhibitor, which also act as a highly selective Cdc25C inhibitor and was about 9-fold potent than that of NSC 663284. Moreover, M2N12 showed remarkable anti-growth activity against the KB-VIN cell line, equivalent to that of PXL and NSC 663284. An all-atom molecular dynamics (MD) simulation approach was further employed to probe the significant selectivity of M2N12 for Cdc25C relative to its structural homologs Cdc25A and Cdc25B. Overall, above results make M2N12 a promising lead compound for further investigation and structural modification.
- Jing, Lanlan,Wu, Gaochan,Hao, Xia,Olotu, Fisayo A.,Kang, Dongwei,Chen, Chin Ho,Lee, Kuo-Hsiung,Soliman, Mahmoud E.S.,Liu, Xinyong,Song, Yuning,Zhan, Peng
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- Optimal Destabilization of DNA Double Strands by Single-Nucleobase Caging
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Photolabile protecting groups are widely used to trigger oligonucleotide activity. The ON/OFF-amplitude is a critical parameter. An experimental setup has been developed to identify protecting group derivatives with superior caging properties. Bulky rests
- Seyfried, Patrick,Heinz, Marcel,Pintér, Gy?rgy,Kl?tzner, Dean-Paulos,Becker, Yvonne,Bolte, Michael,Jonker, Hendrik R. A.,Stelzl, Lukas S.,Hummer, Gerhard,Schwalbe, Harald,Heckel, Alexander
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supporting information
p. 17568 - 17576
(2018/11/10)
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- 1,3,5-triazaspiro[5.5]undeca-2,4-dienes as selective Mycobacterium tuberculosis dihydrofolate reductase inhibitors with potent whole cell activity
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The emergence of multi- and extensively-drug resistant tubercular (MDR- and XDR-TB) strains of mycobacteria has limited the use of existing therapies, therefore new drugs are needed. Dihydrofolate reductase (DHFR) has recently attracted much attention as
- Yang, Xuan,Wedajo, Wassihun,Yamada, Yoshiyuki,Dahlroth, Sue-Li,Neo, Jason Jun-Long,Dick, Thomas,Chui, Wai-Keung
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p. 262 - 276
(2017/12/28)
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- Discovery of Novel 11-Triazole Substituted Benzofuro[3,2-b]quinolone Derivatives as c-myc G-Quadruplex Specific Stabilizers via Click Chemistry
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The specificity of nucleic acids' binders is crucial for developing this kind of drug, especially for novel G-quadruplexes' binders. Quindoline derivatives have been developed as G-quadruplex stabilizers with good interactive activities. In order to improve the selectivity and binding affinity of quindoline derivatives as c-myc G-quadruplex binding ligands, novel triazole containing benzofuroquinoline derivatives (T-BFQs) were designed and synthesized by using the 1,3-dipolar cycloaddition of a series of alkyne and azide building blocks. The selectivity toward c-myc G-quadruplex DNA of these novel T-BFQs was significantly improved, together with an obvious increase on binding affinity. Further cellular and in vivo experiments indicated that the T-BFQs showed inhibitory activity on tumor cells' proliferation, presumably through the down-regulation of transcription of c-myc gene. Our findings broadened the modification strategies of specific G-quadruplex stabilizers.
- Zeng, De-Ying,Kuang, Guo-Tao,Wang, Shi-Ke,Peng, Wang,Lin, Shu-Ling,Zhang, Qi,Su, Xiao-Xuan,Hu, Ming-Hao,Wang, Honggen,Tan, Jia-Heng,Huang, Zhi-Shu,Gu, Lian-Quan,Ou, Tian-Miao
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supporting information
p. 5407 - 5423
(2017/07/22)
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- New Caffeic Acid Phenylethyl Ester Analogs Bearing Substituted Triazole: Synthesis and Structure-Activity Relationship Study towards 5-Lipoxygenase Inhibition
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Leukotrienes are biosynthesized by the conversion of arachidonic acid by 5-Lipoxygenase and play a key role in many inflammatory disorders. Inspired by caffeic acid phenylethyl ester (CAPE) (2) and an analog carrying a triazole substituted by cinnamoyl an
- Roy, Pierre-Philipe,Faye, Diene,Blanchard, Sébastien,Cormier, Marc,Doiron, Jérémie A.,Surette, Marc E.,Touaibia, Mohamed
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- Pd/C Catalyzed Carbonylation of Azides in the Presence of Amines
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A facile and efficient Pd/C-catalyzed carbonylation of both aliphatic and aromatic azides in the presence of amines is reported. Serving as the widely existed fragments in an array of biological pharmaceuticals, functionalized unsymmetrical ureas were str
- Zhao, Jin,Li, Zongyang,Yan, Shuaihu,Xu, Shiyang,Wang, Ming-An,Fu, Bin,Zhang, Zhenhua
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supporting information
p. 1736 - 1739
(2016/05/19)
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- A straightforward and versatile approach to the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from alkyl halides via a one-pot, three-component reaction
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The preparation of 1,4,5-trisubstituted 1,2,3-triazoles by the coupling of three components (alkyl halides, sodium azide, and active ketones) through an azide-enolate [3+2] cycloaddition (Dimroth cycloaddition) has been developed for the first time. A wide variety of halides (including chlorides, bromides, and iodides as well as primary and secondary derivatives) have demonstrated the versatility of this method, which is based on a one-pot system under mild reaction conditions.
- González-Calderón, Davir,Aguirre-De Paz, José G.,González-González, Carlos A.,Fuentes-Benítes, Aydeé,González-Romero, Carlos
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p. 1713 - 1715
(2015/03/14)
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- Palladium-catalyzed cross-coupling reaction of azides with isocyanides
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An efficient palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides with excellent yields. This method shows a broad substrate scope, including not only aryl azides, but also unactivated benzyl and alkyl azides. Furthermore, from readily available substrates, Pd-catalyzed coupling with a tandem amine insertion cascade to obtain unsymmetric trisubstituted guanidines has been achieved in a one-pot fashion.
- Zhang, Zhen,Li, Zongyang,Fu, Bin,Zhang, Zhenhua
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supporting information
p. 16312 - 16315
(2015/11/16)
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- Using the same hydroxamic acid derivative and HDAC8 inhibitor (by machine translation)
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Disclosed are: a compound which is capable of inhibiting the function of HDAC8; and an HDAC8 inhibitor. Specifically disclosed is a hydroxamic acid derivative which is characterized by being composed of a compound represented by general formula (1) (wherein X represents an aromatic substituent or an optionally substituted 3-8 membered ring, and n represents an integer of 0-20), or a pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof.
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Paragraph 0053; 0054
(2016/10/09)
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- A dicationic, podand-like, ionic liquid water system accelerated copper-catalyzed azide-alkyne click reaction
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In this work, an effective, task specific, dicationic, podand-like ionic liquid was synthesized and applied to improve the capability features of click reaction. Moreover, to broaden the scope and decreasing the serious limitations of preparation methods of organic azides, a simple green procedure for the preparation of alkyl azides, the fundamental starting materials in click reactions, from alcohols under solvent-free conditions and microwave irradiation has been reported, for the first time.
- Javaherian, Mohammad,Kazemi, Foad,Ghaemi, Masoumeh
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p. 1643 - 1647
(2015/01/09)
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- Toward analogues of MraY natural inhibitors: Synthesis of 5′-triazole-substituted-aminoribosyl uridines through a Cu-catalyzed azide-alkyne cycloaddition
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A straightforward strategy for the synthesis of triazole-containing MraY inhibitors has been developed. It involves the sequential introduction of a terminal alkyne at the 5′ position of an uridine derivative and O-glycosylation with a protected aminoribose leading to an elaborated alkyne scaffold. An efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) allowed the introduction of chemical diversity toward a small library of inhibitors.
- Fer, Mickael J.,Olatunji, Samir,Bouhss, Ahmed,Calvet-Vitale, Sandrine,Gravier-Pelletier, Christine
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p. 10088 - 10105
(2013/11/06)
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- Alkyne phosphonites for sequential azide-azide couplings
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When Staudinger meets Huisgen! A combination of the copper-catalyzed variant of the Huisgen azide-alkyne cycloaddition (CuAAC) and the Staudinger reaction, the two most successful chemoselective reactions for the transformation of azides, leads to a chemi
- Vallée, M. Robert J.,Artner, Lukas M.,Dernedde, Jens,Hackenberger, Christian P. R.
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supporting information
p. 9504 - 9508
(2013/09/23)
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- Direct C-H amination of arenes with alkyl azides under rhodium catalysis
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New horizons in the utility of azides: The rhodium-catalyzed intermolecular direct C-H amination of arenes with alkyl azides provides a convenient route to N-alkyl anilines (see scheme; DG=directing group). Alkyl azides with a wide range of functional groups reacted readily with various substrates, including benzamides, aromatic ketones, and flavones. Copyright
- Shin, Kwangmin,Baek, Yunjung,Chang, Sukbok
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supporting information
p. 8031 - 8036
(2013/08/23)
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- Unexpected conversion of alkyl azides to alkyl iodides and of aryl azides to N-tert-butyl anilines
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In the presence of tert-butyl iodide, alkyl azides are converted into the corresponding iodides at room temperature, whereas, N-t-Bu anilines are obtained from aryl azides under the same experimental conditions. A mechanism is proposed to explain this unusual reactivity.
- Maury, Julien,Feray, Laurence,Bertrand, Michele P.,Kapat, Ajoy,Renaud, Philippe
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p. 9606 - 9611,6
(2020/08/20)
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- Rapid discovery of highly potent and selective inhibitors of histone deacetylase 8 using click chemistry to generate candidate libraries
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To find HDAC8-selective inhibitors, we designed a library of HDAC inhibitor candidates, each containing a zinc-binding group that coordinates with the active-site zinc ion, linked via a triazole moiety to a capping structure that interacts with residues on the rim of the active site. These compounds were synthesized by using click chemistry. Screening identified HDAC8-selective inhibitors including C149 (IC50 = 0.070 μM), which was more potent than PCI-34058 (6) (IC50 = 0.31 μM), a known HDAC8 inhibitor. Molecular modeling suggested that the phenylthiomethyl group of C149 binds to a unique hydrophobic pocket of HDAC8, and the orientation of the phenylthiomethyl and hydroxamate moieties (fixed by the triazole moiety) is important for the potency and selectivity. The inhibitors caused selective acetylation of cohesin in cells and exerted growth-inhibitory effects on T-cell lymphoma and neuroblastoma cells (GI50 = 3-80 μM). These findings suggest that HDAC8-selective inhibitors have potential as anticancer agents.
- Suzuki, Takayoshi,Ota, Yosuke,Ri, Masaki,Bando, Masashige,Gotoh, Aogu,Itoh, Yukihiro,Tsumoto, Hiroki,Tatum, Prima R.,Mizukami, Tamio,Nakagawa, Hidehiko,Iida, Shinsuke,Ueda, Ryuzo,Shirahige, Katsuhiko,Miyata, Naoki
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p. 9562 - 9575
(2013/01/16)
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- Reductive azidation of carbonyl compounds via tosylhydrazone intermediates using sodium azide
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Simple and direct: Aldehydes and ketones can be transformed into alkyl azides through a reductive coupling of the corresponding tosylhydrazones in a process that takes place simply in the presence of K2CO3, tetrabutylammonium bromide
- Barluenga, Jose,Tomas-Gamasa, Maria,Valdes, Carlos
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supporting information; experimental part
p. 5950 - 5952
(2012/07/03)
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- Direct synthesis of organic azides from alcohols using 2-azido-1,3- dimethylimidazolinium hexafluorophosphate
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Direct synthesis of organic azides from alcohols was developed. Azide transfer of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP) to alcohols proceeds to give the corresponding azides under mild reaction conditions, which were easily isolated because the byproducts are highly soluble in water. Georg Thieme Verlag Stuttgart · New York.
- Kitamura, Mitsuru,Koga, Tatsuya,Yano, Masakazu,Okauchi, Tatsuo
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experimental part
p. 1335 - 1338
(2012/07/13)
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- Peptoid-Peptide Hybrid Ligands Targeting the Polo Box Domain of Polo-Like Kinase 1
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We replaced the amino terminal Pro residue of the Plk1 polo-box-domain-binding pentapeptide (PLHSpT) with a library of N-alkyl-Gly peptoids , and identified long-chain tethered phenyl moieties giving greater than two-orders-of-magnitude affinity enhancement. Further simplification by replacing the peptoid residue with appropriate amides gave low-nanomolar affinity N-acylated tetrapeptides. Binding of the N-terminal long-chain phenyl extension was demonstrated by X-ray co-crystal data.
- Liu, Fa,Park, Jung-Eun,Qian, Wen-Jian,Lim, Dan,Scharow, Andrej,Berg, Thorsten,Yaffe, Michael B.,Lee, Kyung S.,Burke Jr., Terrence R.
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body text
p. 1291 - 1296
(2012/09/08)
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- Flow synthesis of organic azides and the multistep synthesis of imines and amines using a new monolithic triphenylphosphine reagent
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Here we describe general flow processes for the synthesis of alkyl and aryl azides, and the development of a new monolithic triphenylphosphine reagent, which provides a convenient format for the use of this versatile reagent in flow. The utility of these new tools was demonstrated by their application to a flow Staudinger aza-Wittig reaction sequence. Finally, a multistep aza-Wittig, reduction and purification flow process was designed, allowing access to amine products in an automated fashion.
- Smith, Catherine J.,Smith, Christopher D.,Nikbin, Nikzad,Ley, Steven V.,Baxendale, Ian R.
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supporting information; experimental part
p. 1927 - 1937
(2011/04/21)
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- Facile synthesis of 4-vinyl- and 4-fluorovinyl-1,2,3-triazoles via bifunctional "click-olefination" reagents
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Modular synthesis of vinyl and fluorovinyl triazoles can be achieved from bifunctional propargyl and fluoropropargyl sulfones by Cu-catalyzed azide-alkyne ligation and Julia-Kocienski olefination. Competitive click reactions of the protio and fluoropropar
- Kumar, Rakesh,Pradhan, Padmanava,Zajc, Barbara
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supporting information; experimental part
p. 3891 - 3893
(2011/05/03)
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- Lewis acid or alkyl halide promoted rearrangements of phosphor- and phosphinimidates to N,N-disubstituted phosphor- and phosphinamidates
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In this paper, we describe the synthesis of N,N-disubstituted phosphor- and phosphinamidates via alkyl halide or Lewis acid catalyzed rearrangements of phosphor- or phosphinimidates. Furthermore, we introduce a novel one-pot procedure for the synthesis of N,N-disubstituted phosphoramidates which prevents the isolation of potentially explosive alkyl azide derivatives. In this reaction sequence, several alkyl halides are converted in situ into the corresponding azides and reacted with phosphites to generate phosphorimidates. Final addition of a catalytic amount of Lewis acid to the mixture affords the N,N-disubstituted phosphoramidates in good to excellent overall yields. 1 Introduction 2 Synthesis of N,N-Disubstituted Phosphor- and Phosphinamidates 2.1 Alkyl Halide Catalyzed Rearrangement of Phosphin- and Phosphorimidates 2.2 Lewis Acid Catalyzed Rearrangement of Phosphin- and Phosphorimidates 2.3 One-Pot Procedure for the Formation of N,N-Disubstituted Phosphoramidates from Alkyl Halides 3 Conclusion. Georg Thieme Verlag Stuttgart - New York.
- Wilkening, Ina,Del Signore, Giuseppe,Ahlbrecht, Wiebke,Hackenberger, Christian P. R.
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experimental part
p. 2709 - 2720
(2011/10/18)
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- Sequential one-pot ruthenium-catalyzed azide-alkyne cycloaddition from primary alkyl halides and sodium azide
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An experimentally simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating the primary alkyl halide with sodium azide in DMA under microwave heating. Subsequent addition of [RuClCp*(PPh 3)2] and the alkyne yielded the desired cycloaddition product after further microwave irradiation.
- Johansson, Johan R.,Lincoln, Per,Norden, Bengt,Kann, Nina
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experimental part
p. 2355 - 2359
(2011/05/13)
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- A novel potent nicotinamide phosphoribosyltransferase inhibitor synthesized via click chemistry
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The inhibition of NAD synthesis or salvage pathways has been proposed as a novel target for antitumoral drugs. Two molecules with this mechanism of action are at present undergoing clinical trials. In searching for similar novel molecules, we exploited co
- Colombano, Giampiero,Travelli, Cristina,Galli, Ubaldina,Caldarelli, Antonio,Chini, Maria Giovanna,Canonico, Pier Luigi,Sorba, Giovanni,Bifulco, Giuseppe,Tron, Gian Cesare,Genazzani, Armando A.
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supporting information; experimental part
p. 616 - 623
(2010/07/06)
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- Click-based synthesis and proteomic profiling of lipstatin analogues
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Using click chemistry to enable both structural diversity and proteome profiling within a natural product derived library, two out of nineteen lipstatin analogues showed similar activity to Orlistat against fatty acid synthase (FAS), but with an improved
- Ngai, Mun H.,Yang, Peng-Yu,Liu, Kai,Shen, Yuan,Wenk, Markus R.,Yao, Shao Q.,Lear, Martin J.
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supporting information; experimental part
p. 8335 - 8337
(2010/12/25)
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- An unexpected example of protein-templated click chemistry
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(Figure Presented) It all happened with a click: In a search for histone deacetylase (HDAC) inhibitors using in situ click chemistry, the first example of protein-Cu acceleration of the azide-alkyne cycloaddition reaction was uncovered. The copper center
- Suzuki, Takayoshi,Ota, Yosuke,Kasuya, Yuki,Mutsuga, Motoh,Kawamura, Yoko,Tsumoto, Hiroki,Nakagawa, Hidehiko,Finn,Miyata, Naoki
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supporting information; experimental part
p. 6817 - 6820
(2010/12/19)
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- Synthesis of antitumour (1H-1,2,3-triazol-4-yl)-4-hydroxycyclohexa-2,5- dien-1-ones by copper-catalysed Huisgen cycloadditions
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4-Ethynyl-4-hydroxycyclohexa-2,5-dien-1-one 5 undergoes cycloaddition reactions with a range of substituted azides in the presence of copper salts to form 1,4-disubstituted triazoles 8-11 bearing the 4-hydroxycyclohexa-2,5-dien-1- one (quinol) pharmacopho
- McCarroll, Andrew J.,Matthews, Charles S.,Wells, Geoffrey,Bradshaw, Tracey D.,Stevens, Malcolm F. G.
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body text
p. 2078 - 2084
(2010/07/04)
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- A convenient and efficient synthesis of C-carbamoyl-1,2,3-triazoles from alkyl bromide by a one-pot sequential addition: Conversion of ester to amide using Zr(Ot-Bu)4
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A convenient and efficient one-pot sequence has been developed for the synthesis of C-carbamoyl-1,2,3-triazoles from alkyl bromide using (i) sodium azide, (ii) methyl propiolate and copper iodide, and (iii) amines, zirconium tert-butoxide, and 1-hydroxybe
- Yang, Dongsik,Kwon, Mihyun,Jang, Yujin,Jeon, Heung Bae
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experimental part
p. 3691 - 3695
(2010/08/20)
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- Copper/HP20: Novel and polymer-supported copper catalyst for huisgen cycloaddition
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A polymer-supported copper catalyst (Cu/HP20) is easily prepared in water and effectively catalyzed the Huisgen cycloaddition between azides and terminal alkynes.
- Kitamura, Yoshiaki,Taniguchi, Kazumi,Maegawa, Tomohiro,Monguchi, Yasunari,Kitade, Yukio,Sajiki, Hironao
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experimental part
p. 521 - 532
(2009/09/06)
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- INHIBITION AND DISPERSION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES
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Disclosure is provided for imidazole-triazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.
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(2009/10/30)
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- Stereoretentive halogenations and azidations with titanium(IV) enabled by chelating leaving groups
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Titaniumdoes it again! With the help of nucleophile-assisting leaving groups (NALGs), alkyl bromides, iodides, and, for the first time, azides are obtained from sulfonates withcomplete retention of configuration. Critical to the design of these new titanium(IV) reactions has been the use of NALGs which are thought to chelate the Lewis acid reagent in the transition state promoting an SNi-type mechanism. (Chemical Equation Presented)
- Lepore, Salvatore D.,Mondal, Deboprosad,Song, Ye Li,Bhunia, Anjan K.
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supporting information; body text
p. 7511 - 7514
(2009/03/12)
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- Synthesis of sulfoximidoyl-substituted triazoles by huisgen 1,3-dipolar cycloaddition
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The reaction of alkynyl sulfoximines with in situ prepared organic azides in water-dichloromethane under reflux affords sulfoximidoyl-substituted triazoles by Huisgen 1,3-dipolar cycloaddition. Georg Thieme Verlag Stuttgart.
- Füger, Bernhard,Sklute, Genia,Marek, Ilan,Bolm, Gae Young,Bolm, Carsten
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p. 116 - 118
(2008/09/21)
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- Histone deacetylase inhibitors through click chemistry
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Histone deacetylase inhibitors (HDACi) are a relatively new class of chemotherapy agents. Herein, we report a click-chemistry based approach to the synthesis of HDACi. Fourteen agents were synthesized from the combination of two alkyne and seven azido pre
- Shen, Jie,Woodward, Robert,Kedenburg, James Patrick,Liu, Xianwei,Chen, Min,Fang, Lanyan,Sun, Duxin,Wang, Peng George
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experimental part
p. 7417 - 7427
(2009/12/26)
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- Synthesis and evaluation of novel heterocyclic MMP inhibitors
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A variety of novel heterocyclic compounds were synthesized and evaluated for MMP inhibition. Broad spectrum inhibition of MMPs 1, 2, 9, and 12 was found with pyridinone-based compounds while N-heterocyclic triazoles and tetrazoles were largely ineffective. A highly selective tetrazole inhibitor for MMP-2 was discovered.
- Hayashi, Ryuji,Jin, Xiaomin,Cook, Gregory R.
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p. 6864 - 6870
(2008/09/18)
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- A simple one-pot procedure for the direct conversion of alcohols into azides using TsIm
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A facile and efficient method for one-pot conversion of alcohols into azides using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, alcohols are refluxed with a mixture of NaN3, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in DMF affording the corresponding alkyl azides in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1° > 2° > 3°.
- Soltani Rad, Mohammad Navid,Behrouz, Somayeh,Khalafi-Nezhad, Ali
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p. 3445 - 3449
(2008/02/10)
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- PROCESS FOR THE PRODUCTION OF COMPOUNDS VIA HAZARDOUS INTERMEDIATES IN A SERIES OF MICROREACTORS
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Multi-step process for the preparation of compounds via hazardous intermediates comprising the steps of a) preparing in a microreactor a hazardous intermediate and b) optionally performing one or more reaction steps on the hazardous intermediate in one or more additional microreactors and c) further converting the hazardous intermediate with a suitable reaction agent in a subsequent microreactor until a stable end product is formed.
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Page/Page column 14
(2008/06/13)
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- Radical reduction of aromatic azides to amines with triethylsilane
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Aromatic azides are inert toward triethylsilane under thermal conditions in the presence of a radical initiator, but in the presence of additional catalytic amounts of tert-dodecanethiol, they afford anilinosilanes and thence the corresponding anilines in virtually quantitative yields.
- Benati, Luisa,Bencivenni, Giorgio,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Scialpi, Rosanna,Spagnolo, Piero,Zanardi, Giuseppe
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p. 5822 - 5825
(2007/10/03)
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- Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone in the presence of n-Bu4NN3 is a useful system for efficient conversion of tetrahydropyranyl (THP) ethers to their corresponding alkyl azides
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Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/tetrabutylammonium azide was used as an efficient system in conversion of tetrahydropyranyl ethers to corresponding alkyl azides. Copyright Taylor & Francis Inc.
- Akhlaghinia, Batool
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p. 1601 - 1604
(2007/10/03)
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- TACHYKININ RECEPTOR ANTAGONISTS
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The present invention relates to selective NK-1 receptor antagonists of Formula (I) or a pharmaceutically acceptable salt thereof, for the treatment of disorders associated with an excess of tachykinins.
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- A novel and highly selective conversion of alcohols, thiols, and silyl ethers to azides using the triphenylphosphine/2,3-dichloro-5,6- dicyanobenzoquinone(DDQ)/n-Bu4NN3 system
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Alcohols, thiols, and silyl ethers are converted into alkyl azides in good to excellent yields by treatment with PPh3/DDQ/n-Bu 4NN3 in CH2Cl2 at room temperature. The method is highly selective for 1°
- Iranpoor, Nasser,Firouzabadi, Habib,Akhlaghinia, Batool,Nowrouzi, Najmeh
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p. 3291 - 3294
(2007/10/03)
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- A real time reaction monitoring using fluorescent dansyl group as a solid-phase leaving group
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A real time monitoring method to monitor the progress of the solid-phase reaction has been developed. The substitution reaction on the solid-phase was clearly monitored as a change in the color depth using the fluorescent dansyl group as the leaving group. This methodology is applicable to both parallel and split combinatorial synthesis.
- Suenaga, Toshiro,Schutz, Caroline,Nakata, Tadashi
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p. 5799 - 5801
(2007/10/03)
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