- Mono- and dinuclear palladium(II) complexes incorporating 1,2,3-triazole-derived mesoionic carbenes: syntheses, solid-state structures and catalytic applications
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Two 1,2,3-triazole-derived monocationic salts 3 and 4 bearing N-aryl wingtips were prepared using copper-catalyzed “click” reactions followed by alkylations with iodomethane. Employing a silver–carbene transfer method, two dinuclear palladium(II) complexes of triazolin-5-ylidenes (5/6) were obtained, the former of which has been reported previously. Bridge-cleavage reaction of 5 as a representative with PPh3 yielded cis-configured mesoionic carbene/phosphine hybrid complex cis-7 and homoleptic bis(phosphine) complex 8, suggesting the presence of a ligand exchange process. In contrast, bridge breakages of 5/6 with pyridine cleanly afforded PEPPSI-type complexes 9 and 10 in near quantitative yields. Finally, all complexes were exploited to catalyze Mizoroki–Heck coupling reactions with aryl bromides as the substrates, and PEPPSI-type complex 9 was found to be the best performer generally giving good to excellent yields.
- Zhang, Xin,Yan, Xuechao,Zhang, Bo,Wang, Ran,Guo, Shuai,Peng, Shiyong
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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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- Synthesis of novel 1,2,3-triazole based artemisinin derivatives and their antiproliferative activity
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Two series of novel 1,2,3-triazole based artemisinin derivatives were designed, synthesized via a copper(i)-catalyzed azide alkyne cycloaddition (CuAAC) reaction and investigated for their antiproliferative activity by MTT assay against various human canc
- Kapkoti, Deepak Singh,Singh, Shilpi,Luqman, Suaib,Bhakuni, Rajendra Singh
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p. 5978 - 5995
(2018/04/23)
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- One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes
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A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.
- Zhao, Fen,Chen, Zhen,Xie, Kai,Yang, Rui,Jiang, Yu-Bo
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p. 109 - 113
(2016/01/25)
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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 library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: Design, synthesis, and biological evaluation
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A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(i) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The anti-proliferative evaluation indicated that some compounds exhibited exc
- Wei, Gaofei,Luan, Weijing,Wang, Shuai,Cui, Shanshan,Li, Fengran,Liu, Yongxiang,Liu, Yang,Cheng, Maosheng
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p. 1507 - 1514
(2015/01/30)
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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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- Zinc mediated azide-alkyne ligation to 1,5- and 1,4,5-substituted 1,2,3-triazoles
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A mild method for regioselective formation of 1,5-substituted 1,2,3-triazoles is described. The zinc-mediated reaction works at room temperature and is successful across a wide range of azido/alkynyl substrates. Additionally, the triazole 4-position can be further functionalized through the intermediate aryl-zinc to accommodate a diverse three-component coupling strategy.
- Smith, Christopher D.,Greaney, Michael F.
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supporting information
p. 4826 - 4829
(2013/10/08)
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- One-pot chemoenzymatic synthesis of chiral disubstituted 1,2,3-triazoles in aqueous media
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A one-pot, two-step procedure combining 1,3-dipolar cycloaddition and an enantioselective reduction mediated by Daucus carota (carrot root) is described. The synthesis was accomplished by first employing the biocatalyst followed by a "click" reaction unde
- De Souza De Oliveira, Camila,De Andrade, Kleber Tellini,Omori, Alvaro Takeo
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- Simple and efficient method for the preparation of aryl azides using sonication
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An efficient procedure for the preparation of aryl azides using sonication is described. The convenient sonication-mediated azidation protocol is applicable to aryl compounds under mild conditions with aqueous solution of sodium dichloroiodate and sodium
- Telvekar, Vikas N.,Sasane, Kulbhushan A.
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experimental part
p. 1085 - 1089
(2012/02/01)
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- Synthesis of substituted triazolyl curcumin mimics that inhibit RANKL-induced osteoclastogenesis
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Some promising new antiresorptive agents of potential utility for treating osteoporosis were uncovered in a curcumin mimics library possessing a substituted triazole moiety, which is synthesized by the Cu(I)-catalyzed Huisgen 1,3-cycloaddition reaction be
- Park, Sang-Kyu,Oh, Sangtae,Shin, Hye Kyoung,Kim, Seong Hwan,Ham, Jungyeob,Song, Jae-Seok,Lee, Seokjoon
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scheme or table
p. 3573 - 3577
(2011/08/06)
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- Design and synthesis of photoactivatable aryl diketo acid-containing HIV-1 integrase inhibitors as potential affinity probes
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Aryl diketo acids (ADKs) represent an important new class of HIV-1 integrase (IN) inhibitors. In order to facilitate examination of the structural basis underlying IN·ADK interaction, biphenyl ketone and phenyl azide photophores were incorporated into ADK structures. Of particular note is the novel dual utilization of azide and phenyketone moieties for both enzyme recognition and for crosslinking. The resulting analogues maintained low micromolar inhibitory potency against IN in recombinant in vitro assays. These potential HIV-1 integrase photoaffinity labels may provide useful tools for studying enzyme interactions of the ADK inhibitor class.
- Zhang, Xuechun,Marchand, Christophe,Pommier, Yves,Burke Jr., Terrence R.
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p. 1205 - 1207
(2007/10/03)
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- Preparation of fluorinated anilines
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Fluorinated anilines, especially p-fluoroaniline and 2,4-difluoroaniline, are prepared by treating aromatic azides with anhydrous hydrogen fluoride. The aromatic azides, in turn, are prepared from the corresponding anilines by treatment with nitrous acid or salt thereof and an alkali metal azide in the presence of a mineral acid, and in an aqueous-nonaqueous, two-phase environment.
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