6324-18-1Relevant academic research and scientific papers
Application of primary halogenated hydrocarbons for the synthesis of 3-Aryl and 3-Alkyl indolizines
Liu, Yan,Hu, Huayou,Zhou, Junyu,Wang, Wenhui,He, Youliang,Wang, Chao
, p. 5016 - 5024 (2017/07/10)
Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-Alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-Aryl and 3-Alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-Tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and low-cost starting materials, the transition-metal-free conditions and its ready scalability.
Preparation, in vitro screening and molecular modelling of mono-quaternary compounds related to the selective acetylcholinesterase inhibitor BW284c51
Benek, Ondrej,Musilek, Kamil,Horova, Anna,Dohnal, Vlastimil,Dolezal, Rafael,Kuca, Kamil
, p. 21 - 29 (2015/04/14)
This paper describes preparation and in vitro evaluation of 19 compounds related to the selective experimental cholinesterase inhibitor BW284c51. The novel compounds were prepared as fragments of parent molecule BW284c51 and evaluated on the model of human recombinant acetylcholinesterase and human plasmatic butyrylcholinesterase. The IC50 values of the prepared compounds were compared to the parent molecule BW284c51. None of the compounds was superior to the parent drug, but two BW284c51 fragments showed promising hAChE inhibition in μM scale and improved selectivity. These two fragments were further subjected to the molecular modelling study and their enzyme interactions were rationalized. The structure-activity relationship of the prepared series was stated.
High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4- epoxypiperidines with amines - A short-step synthesis of 4- fluorobenzyltrozamicol and novel anilidopiperidines
Scheunemann, Matthias,Hennig, Lothar,Funke, Uta,Steinbach, J?rg
supporting information; experimental part, p. 3448 - 3456 (2011/06/20)
Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4- fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new β-hydroxy substituted anilidopiperidines.
Time-dependent slowly-reversible inhibition of monoamine oxidase A by N-substituted 1,2,3,6-tetrahydropyridines
Wichitnithad, Wisut,O'Callaghan, James P.,Miller, Diane B.,Train, Brian C.,Callery, Patrick S.
experimental part, p. 7482 - 7492 (2012/02/02)
A novel class of N-substituted tetrahydropyridine derivatives was found to have multiple kinetic mechanisms of monoamine oxidase A inhibition. Eleven structurally similar tetrahydropyridine derivatives were synthesized and evaluated as inhibitors of MAO-A and MAO-B. The most potent MAO-A inhibitor in the series, 2,4-dichlorophenoxypropyl analog 12, displayed time-dependent mixed noncompetitive inhibition. The inhibition was reversed by dialysis, indicating reversible enzyme inhibition. Evidence that the slow-binding inhibition of MAO-A with 12 involves a covalent bond was gained from stabilizing a covalent reversible intermediate product by reduction with sodium borohydride. The reduced enzyme complex was not reversible by dialysis. The results are consistent with slowly reversible, mechanism-based inhibition. Two tetrahydropyridine analogs that selectively inhibited MAO-A were characterized by kinetic mechanisms differing from the kinetic mechanism of 12. As reversible inhibitors of MAO-A, tetrahydropyridine analogs are at low risk of having an adverse effect of tyramine-induced hypertension.
Effect of structure of nucleophile and substrate on the quaternization of heterocyclic amines
Zhuravlev,Verolainen,Voronchikhina
, p. 1025 - 1028 (2011/01/11)
The influence of the nature of the quaternizing agent and substrate on the quaternization of heterocyclic amines, derivatives of pyridine, ss-picoline, nicotinamide, pyridoxine, was studied. The synthesized compounds were characterized by IR spectroscopy and elemental analysis. The conclusions were made about the effect of the structure of nucleophile and substrate on the process of quaternization reaction. Pleiades Publishing, Ltd., 2010.
Photocyclization mechanism of halopyridinium salt tethered to arene: Flash photolysis observation of a pyridinium σ, cyclohexadienyl radicals, and a dihalide radical anion in aqueous solution
Park, Yong-Tae,Song, Nam Woong,Hwang, Chul-Gyun,Kim, Kwang-Wook,Kim, Dongho
, p. 10677 - 10683 (2007/10/03)
The photocyclization reactions of 2-halopyridinium salt tethered to arene have been studied. The photocyclization of 2-halophenethylpyridinium salts produced a six-membered heterocyclic product, pyrido[2,1-a]-3H,4H-isoquinolinium salt. The 2-halopyridiniu
