62214-78-2Relevant articles and documents
Synthesis and evaluation of the performance of a small molecule library based on diverse tropane-related scaffolds
Lowe, Robert A.,Taylor, Dale,Chibale, Kelly,Nelson, Adam,Marsden, Stephen P.
supporting information, (2020/03/25)
A unified synthetic approach was developed that enabled the synthesis of diverse tropane-related scaffolds. The key intermediates that were exploited were cycloadducts formed by reaction between 3-hydroxy-pyridinium salts and vinyl sulfones or sulfonamides. The diverse tropane-related scaffolds were formed by addition of substituents to, cyclisation reactions of, and fusion of additional ring(s) to the key bicyclic intermediates. A set of 53 screening compounds was designed, synthesised and evaluated in order to determine the biological relevance of the scaffolds accessible using the synthetic approach. Two inhibitors of Hedgehog signalling, and four compounds with weak activity against the parasite P. falciparum, were discovered. Three of the active compounds may be considered to be indotropane or pyrrotropane pseudo natural products in which a tropane is fused with a fragment from another natural product class. It was concluded that the unified synthetic approach had yielded diverse scaffolds suitable for the design of performance-diverse screening libraries.
A benidipine hydrochloride method for synthesizing intermediate
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Paragraph 0030-0032, (2018/07/30)
The invention discloses a synthetic method for a benidipine hydrochloride intermediate. The synthetic method comprises performing a nucleophilic substitution reaction on 3-hydroxypyridine and a benzyl halide under a solvent refluxing condition, so as to generate 1-benzyl-3-hydroxypyridiniumhalide; taking an alcohol as a solvent and reducing 1-benzyl-3-hydroxypyridiniumhalide to generate 1-benzyl-3-piperidinol; then performing transesterification reaction on 1-benzyl-3-piperidinol and ethyl acetoacetate under a refluxing condition by taking toluene as a solvent in the presence/absence of a catalyst, and under the condition that less than 30% of the alcohol is left, performing normal-pressure distillation until the alcohol completely finishes reaction, so as to obtain the product. The synthetic method is simple and has the three-step total yield of 80% or more, and all employed materials are industrialized products and are cheap and easily obtained, and the quality is easily controlled.
TRICYCLIC COMPOUNDS AND THEIR USE IN THE TREATMENT OF CANCER
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Page/Page column 44, (2017/03/21)
There is provided compounds of formula (I), or pharmaceutically-acceptable salts thereof, wherein X, Y, Z, R1 and R2 have meanings provided in the description, which compounds are useful in the treatment of cancers.
Iridium-catalyzed selective hydrogenation of 3-hydroxypyridinium salts: A facile synthesis of piperidin-3-ones
Huang, Wen-Xue,Wu, Bo,Gao, Xiang,Chen, Mu-Wang,Wang, Baomin,Zhou, Yong-Gui
supporting information, p. 1640 - 1643 (2015/04/14)
The selective hydrogenation of 3-hydroxypyridinium salts has been achieved using a homogeneous iridium catalyst, providing a direct access to 2- and 4-substituted piperidin-3-one derivatives with high yields, which are important organic synthetic intermediates and the prevalent structural motifs in pharmaceutical agents. Mild reaction conditions, high chemoselectivity, and easy scalability make this reaction highly practical for the synthesis of piperidin-3-ones.
Efficient and chemoselective reduction of pyridines to tetrahydropyridines and piperidines via rhodium-catalyzed transfer hydrogenation
Wu, Jianjun,Tang, Weijun,Pettman, Alan,Xiao, Jianliang
supporting information, p. 35 - 40 (2013/03/13)
Promoted by iodide anion the rhodium complex dimer, [Cp RhCl 2]2, catalyzes efficiently the transfer hydrogenation of various quaternary pyridinium salts under mild conditions, affording not only piperidines but also 1,2,3,6-tetrahydropyridines in a highly chemoselective fashion, depending on the substitution pattern at the pyridinium ring. The reduction is conducted in azeotropic formic acid/triethylamine (HCOOH-Et 3N) mixture at 40 °C, with catalyst loadings as low as 0.005mol% being feasible. Copyright
Solid-phase synthesis of functionalized tropane derivatives via 1,3-dipolar cycloaddition
Caix-Haumesser, Sandrine,Hanna, Issam,Lallemand, Jean-Yves,Peyronel, Jean-Fran?ois
, p. 3721 - 3723 (2007/10/03)
1,3-Dipolar cycloaddition of 3-oxidopyridinium betaine to activated olefins on solid-phase leads to resin-bound 8-azabicyclo[3.2.1]octenones which undergo further transformations such as 1,4-addition of nucleophiles. Cleavage of benzyl linker is achieved
Structure of the Calystegines: New alkaloids of the nortropane family
Ducrot,Lallemand
, p. 3879 - 3882 (2007/10/02)
Three new alkaloids have been isolated from Calystegia sepium; their structures have been established from their 1H and 13C N.M.R. spectra, and confirmed by the synthesis of model compounds.
