- N-Heterocyclic carbenes derived from imidazo-[1,5-a]pyridines related to natural products: synthesis, structure and potential biological activity of some corresponding gold(I) and silver(I) complexes
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A series of Au(I) complexes (12, 13, 14, 15, 16) and Ag(I) complexes (17, 18, 19, 20) derived from imidazo[1,5-a]pyridin-3-ylidenes were synthesized from AuCl(SMe2) or by reacting silver(I) acetate with 2,5-dimethylimidazo[1,5-a]pyridin-2-ium iodide or imidazo[1,5-a]pyridin-2-ium salts, and were characterized using NMR spectroscopy, mass spectrometry and elemental analyses. In addition, the Au(I) complex 13 and the Ag(I) complex 19 were characterized using single-crystal X-ray diffraction. Using paclitaxel as a standard, all Au(I) and Ag(I) N-heterocyclic carbene complexes were evaluated for their in vitro anti-tumour activity against 12 cell lines using a monolayer cell survival and proliferation assay. The highest anticancer activity was found for complexes 15, 13 and 14 with mean IC50 values of 10.09, 10.42 and 12.28?μM, respectively. Copyright
- Mihorianu, Monica,Franz, M Heiko,Jones, Peter G,Freytag, Matthias,Kelter, Gerhard,Fiebig, Heinz-Herbert,Tamm, Matthias,Neda, Ion
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- Synthesis of 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands for use in Suzuki-Miyaura cross-coupling reactions
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3-Aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were synthesized from 2-aminomethylpyridine as the initial substrateviatwo complementary routes. The first synthetic pathway underwent the coupling of 2-aminomethylpyridine with substituted benzoyl chlorides, followed by cyclization, iodination and palladium-catalyzed cross-coupling phosphination reactions sequence to give our phosphorus ligands. In the second route, 2-aminomethylpyridine was cyclized with aryl aldehydes, followed by the iodination and palladium-catalyzed cross-coupling phosphination reactions to yield our phosphorus ligands. The 3-aryl-1-phosphinoimidazo[1,5-a]pyridine ligands were evaluated in palladium-catalyzed sterically-hindered biaryl and heterobiaryl Suzuki-Miyaura cross-coupling reactions.
- Dinh, Long P.,Harris, Nekoda W.,Jacoby, Seth A.,Semsey, Rebecca Y.,Swann, William A.,Tran, Ryan Q.,Williamson, Savannah N.,Yet, Larry
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p. 28347 - 28351
(2021/09/15)
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- Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes
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Imidazo[1,5-a]pyridines were efficiently prepared via the cyclization of 2-picolylamines with nitroalkanes electrophilically activated in the presence of phosphorous acid in polyphosphoric acid (PPA) medium.
- Aksenov, Alexander V.,Aksenov, Dmitrii A.,Arutiunov, Nikolai A.,Maliuga, Vladimir V.,Rubin, Michael
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supporting information
p. 2903 - 2910
(2020/12/23)
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- An AcOH-mediated metal free approach towards the synthesis of bis-carbolines and imidazopyridoindole derivatives and assessment of their photophysical properties
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An AcOH-mediated concise, atom-economical and environmentally sustainable tandem strategy has been formulated to access highly fluorescent (ΦF up to 40%) N-fused bis-carbolines, imidazopyrido[3,4-b]indoles and imidazo[1,5-a]pyridines via the formation of three C-N bonds in a single operation. The multicomponent character of the reaction, easy to execute reaction conditions, simple purification procedure and excellent light emitting properties of the product afforded thereof provide a huge scope.
- Singh, Dharmender,Sharma, Shubham,Kumar, Mukesh,Kaur, Inderpreet,Shankar, Ravi,Pandey, Satyendra Kumar,Singh, Virender
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supporting information
p. 835 - 844
(2019/02/01)
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- Formation of Imidazopyridines by the Phase Transfer Catalyzed Reaction of α-(Aminomethyl)pyridines with CHCl3 and Alkaline Hydroxide
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The reaction of chloroform with 2-(aminomethyl)pyridine (1) under basic phase-transfer catalysis affords the highly fluorescent imidazopyridine (2) in 25percent isolated yield.Despite the formation of considerable tarry residue, GC-MS indicates that the volatile fraction of the reaction is simple and consists of 2 and two minor components identified as N-(2-pyridylmethyl)formamide (6) and (2-pyridylmethyl)isonitrile (7).The basic phase transfer catalyzed reaction of chloroform with a series of α-(aminomethyl)azanaphthalenes was found to be general and yield the corresponding annulated imidazo derivatives in comparable yields.Despite product yields in the 25percent range, GC of the reaction mixtures indicates that the volatile fractions generally consist of residual starting aminomethyl compound, the imidazo product, and a minor amount of the (α-azanaphthylmethyl)formamide.However, 3-(aminomethyl)isoquinoline (18) failed to provide any of the expected imidazoisoquinoline (19).The failure to detect 19 was investigated.
- Langry, Kevin C.
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p. 2400 - 2404
(2007/10/02)
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- Antidiabetic pyrrolecarboxylic acids
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Certain pyrrolecarboxylic and pyrroleacetic acid derivatives substituted on the pyrrole ring with thioether groups, acyl groups, phenyl, substituted phenyl, phenoxy, substituted phenoxy, benzyl or halo and optionally substituted on the pyrrole nitrogen with alkyl, and the pharmaceutically acceptable salts thereof, are useful in lowering the blood glucose levels of hyperglycemic animals.
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- Quaternary salts as hypoglycemic agents
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The synthesis of imidazo?1,2-a!pyridinium, imidazo?1,5-a!pyridinium, pyrrolo?1,2-a!pyrazinium, pyrazolo?1,5-a!pyridinium, imidazo?2,1-a!isoquinolinium and imidazo?5,1-a!isoquinolinium quaternary salts and their use as hypoglycemic agents.
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- Imidazopyridinium compounds as hypoglycemic agents
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The synthesis of imidazo[1,2-a]pyridinium, imidazo[1,5-a]pyridinium, pyrrolo[1,2-a]pyrazinium, pyrazolo[1,5-a]pyridinium, imidazo[2,1-a]isoquinolinium and imidazo[5,1-a]isoquinolinium quaternary salts and their use as hypoglycemic agents.
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