- Toward Hypoxia-Selective Rhenium and Technetium Tricarbonyl Complexes
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With the aim of preparing hypoxia-selective imaging and therapeutic agents, technetium(I) and rhenium(I) tricarbonyl complexes with pyridylhydrazone, dipyridylamine, and pyridylaminocarboxylate ligands containing nitrobenzyl or nitroimidazole functional g
- North, Andrea J.,Hayne, David J.,Schieber, Christine,Price, Katherine,White, Anthony R.,Crouch, Peter J.,Rigopoulos, Angela,OKeefe, Graeme J.,Tochon-Danguy, Henri,Scott, Andrew M.,White, Jonathan M.,Ackermann, Uwe,Donnelly, Paul S.
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Read Online
- Ultraviolet photodissociation mass spectrometry of bis-aryl hydrazone conjugated peptides
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Ultraviolet photodissociation (UVPD) at 355 nm was used to rapidly identify peptides which had been chemically conjugated through bis-aryl hydrazone (BAH) moieties. The two biomolecules of interest were separately tagged to introduce either an aldehyde or
- Gardner, Myles W.,Brodbelt, Jennifer S.
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Read Online
- Solvatochromic triazaborolopyridinium probes toward ultra-sensitive trace water detection in organic solvents
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A series of triazaborolopyridiniums (TBP) has been synthesized by varying electron-tunning substituents. The TBP derivatives with electron-withdrawing groups, including cyano, and nitro moieties, exhibited solvatochromic properties due to the internal cha
- Chansaenpak, Kantapat,Namuangruk, Supawadee,Nootem, Jukkrit,Rashatasakhon, Paitoon,Sattayanon, Chanchai,Tumcharern, Gamolwan,Wattanathana, Worawat
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- A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation
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Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.
- Zhang, Yanhui,Teng, Hao,Gao, Ying,Afzal, Muhammad Wasim,Tian, Jingye,Chen, Xi,Tang, Haoyang,James, Tony D.,Guo, Yuan
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supporting information
p. 2917 - 2920
(2020/03/13)
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- Synthesis method for 1,2,4-triazolopyridine derivative
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The invention provides a novel synthesis method for a 1,2,4-triazolopyridine derivative. According to the invention, the 1,2,4-triazolopyridine derivative can be obtained by taking a 2-pyridine hydrazone derivative and sodium hypochlorite as main synthesis raw materials through a reaction for 1-24 hours in an organic solvent at a temperature of 0-100 DEG C. The invention provides a synthetic method which is good in atom economy, mild in reaction conditions, simple and convenient to operate and easy to be controlled for the 1,2,4-triazolopyridine derivative.
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Paragraph 0010
(2020/06/02)
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- 1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA
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Two new cationic DNA intercalators, 3-phenyl-1-(6-phenylpyridin-2-yl)-1H-[1,2,4]triazolo[4,3-a]pyridin-4-ium (1a)+ and 1-phenyl-3-(6-phenylpyridin-2-yl)-3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium (1b)+, were synthesized from 2-chloropyridine and 2-chloroquinoline, respectively, in a four-step procedure. Generation of the hydrazine, followed by condensation with an aldehyde to give a hydrazone and subsequent Buchwald-Hartwig amination gave a mixture of E- and Z-configured N,N-functionalized hydrazones. Finally, oxidative cyclisation gave rise to the formation of the cationic DNA intercalators, whose molecular structures were determined by single-crystal X-ray diffraction analysis of the hexafluorophosphate and tribromide salt of (1a)+ and (1b)+, respectively. The intercalative binding of (1a)PF6 and (1b)PF6 to ctDNA was confirmed by means of UV, CD and luminescence spectroscopy, determination of the DNA melting temperature and by rheology measurements.
- Hebenbrock, Marian,Müller, Jens
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p. 885 - 893
(2018/09/06)
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- Electrochemical synthesis of 1,2,4-triazole-fused heterocycles
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A reagent-free intramolecular dehydrogenative C-N cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free protocol which can be carried out on a gram scale easily. This novel method was applied to the synthesis of one of the top-selling drugs Xanax and late stage functionalization for generating chemical diversity in biologically relevant lead molecules.
- Ye, Zenghui,Ding, Mingruo,Wu, Yanqi,Li, Yong,Hua, Wenkai,Zhang, Fengzhi
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supporting information
p. 1732 - 1737
(2018/04/30)
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- Synthesis of 1,2,4-Triazolo[4,3-a]pyridines and Related Heterocycles by Sequential Condensation and Iodine-Mediated Oxidative Cyclization
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A facile and efficient approach to access 1,2,4-triazolo[4,3-a]pyridines and related heterocycles has been accomplished through condensation of readily available aryl hydrazines with corresponding aldehydes followed by iodine-mediated oxidative cyclizatio
- Li, Ertong,Hu, Zhiyuan,Song, Lina,Yu, Wenquan,Chang, Junbiao
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p. 11022 - 11027
(2016/07/27)
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- A Convenient One-Pot Synthesis of Triazolopyridine and Related Heterocycle Fused-Triazole Analogs Through Copper Catalyzed Oxidative Cyclization Strategy
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One-pot synthesis of heterocycle fused-triazole analogs from the corresponding aldehydes and heteroarylhydrazines is demonstrated. Transformation of hydrazones to the desired systems was achieved by employing the oxidative cyclization with catalytic CuBr2 and oxone. This reaction condition is mild and selective, and a wide range of functional groups were able to sustain. An array of biologically important triazolopyridines, triazolopyridazines, triazolopyrimidines, and triazoloquinolines were obtained in fairly good yield.
- Srinivasan,Sembian Ruso,Nagarajan,Senthil Kumaran,Manickam
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p. 606 - 614
(2016/04/19)
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- Molecular and electronic structure of nonradical homoleptic pyridyl-azo-oxime complexes of cobalt(iii) and the azo-oxime anion radical congener: An experimental and theoretical investigation
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The reaction between a potential flexidentate pyridyl-azo-oxime HL 1 and Co(ClO4)2 yields novel homoleptic complexes of types [CoIII(L-I)3], 2 and [CoIII(L -I)2]ClOsu
- Pramanik, Shuvam,Roy, Sima,Ghorui, Tapas,Ganguly, Sanjib,Pramanik, Kausikisankar
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p. 5317 - 5334
(2014/04/03)
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- Solubility and transfer processes of some hydrazones in biologically relevant solvents
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Solubility values of 20 hydrazones in water, 1-octanol and hexane were determined by the isothermal saturation method. Thermophysical characteristics of fusion processes (melting points and fusion enthalpies) of the selected substances were measured by DS
- Perlovich, German L.,Kazachenko, Vladimir P.,Strakhova, Nadezda N.,Schaper, Klaus-J.,Raevsky, Oleg A.
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p. 2659 - 2667
(2013/09/24)
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- 1,3-dipolar cycloaddition of hydrazones with α-oxo-ketenes: A three-component stereoselective entry to pyrazolidinones and an original class of spirooxindoles
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Stereodefined monocyclic, spirobicyclic, and bis-spirotricyclic pyrazolidin-3-ones can be prepared efficiently by a three-component reaction involving a 1,3-dipolar cycloaddition of azomethine imines obtained from hydrazones with α-oxo-ketene dipolarophiles generated in situ. The reaction allows the creation of four covalent bonds and two contiguous chiral quaternary centers with excellent diastereoselectivity in a single catalyst/additive-free, highly atom-economical transformation. From a fundamental point of view, the reaction introduces α-oxo-ketenes as effective dipolarophiles in 1,3-dipolar cycloadditions.
- Presset, Marc,Mohanan, Kishor,Hamann, Marie,Coquerel, Yoann,Rodriguez, Jean
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supporting information; experimental part
p. 4124 - 4127
(2011/10/04)
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- Palladium-catalyzed coupling of aldehyde-derived hydrazones: Practical synthesis of triazolopyridines and related heterocycles
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The palladium-catalyzed intermolecular coupling of aldehyde-derived hydrazones with chloroazines, followed by oxidative cyclization under mild conditions afforded access to a broad variety of bicyclic heterocyclic scaffolds (see scheme) that have potentia
- Thiel, Oliver R.,Achmatowicz, Michal M.,Reichelt, Andreas,Larsen, Robert D.
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supporting information; experimental part
p. 8395 - 8398
(2010/12/25)
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