134256-32-9Relevant articles and documents
Targeting Alzheimer's disease by investigating previously unexplored chemical space surrounding the cholinesterase inhibitor donepezil
van Greunen, Divan G.,Cordier, Werner,Nell, Margo,van der Westhuyzen, Chris,Steenkamp, Vanessa,Panayides, Jenny-Lee,Riley, Darren L.
, p. 671 - 690 (2017/02/10)
A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the replacement of the piperidine ring in donepezil with different sized saturated N-containing ring systems and the second looking at the introduction of different linkers between the indanone and piperidine rings in donepezil. The most active analogue 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (67) afforded an in vitro IC50value of 0.03 ± 0.07 μM against acetylcholinesterase with no cytotoxicity observed (IC50of >100 μM, SH-SY5Y cell line). In comparison donepezil had an IC50of 0.05 ± 0.06 μM and an observed cytotoxicity IC50of 15.54 ± 1.12 μM. Molecular modelling showed a strong correlation between activity and in silico binding in the active site of acetylcholinesterase.
USE OF AMINOINDANE COMPOUNDS IN TREATING OVERACTIVE BLADDER AND INTERSTITIAL CYSTITIS
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Page/Page column 132-133, (2014/03/22)
The present application provides methods of using the aminoindane compounds of formula (I) or (II) in treating an overactive bladder or interstitial cystitis by administering one or more of the compounds to a patient.
Electrooxidative cyclization of hydroxyamino compounds possessing a benzyl group
Okimoto, Mitsuhiro,Ohashi, Kousuke,Yamamori, Haruki,Nishikawa, Shinnosuke,Hoshi, Masayuki,Yoshida, Takashi
experimental part, p. 1315 - 1322 (2012/06/30)
Several novel 2-aryl-1,3-oxazinane and 2-aryl-1,3-oxazolidine derivatives were synthesized from N-benzyl-2-piperidineethanols and N-benzyl-2- piperidinemethanols, respectively, by using electrooxidative methods in methanol. For these reactions, the yields of the corresponding cyclized compounds were significantly increased by using catalytic amounts of iodide ions. In contrast, 3-dialkylamino-1-phenylpropanols afforded the expected cyclic 6-phenyl-1,3-oxazinane derivatives using only a small excess of base. Georg Thieme Verlag Stuttgart · New York.
Aminoindane Compounds and Use Thereof in Treating Pain
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Page/Page column 75, (2012/09/05)
The present application provides novel aminoindane compounds and methods for preparing and using these compounds. These compounds are useful in treating pain and/or itch in patients by administering one or more of the compounds to a patient. The methods include administering a compound of formula (I) or (II) and a TRPV 1 receptor activator. In one embodiment, the TRPV 1 receptor activator is lidocaine.
Novel application of electrooxidative method for the cyclization of N-benzyl-2-(hydroxymethyl)-and N-benzyl-2-(2-hydroxyethyl)piperidines
Okimoto, Mitsuhiro,Yoshida, Takashi,Hoshi, Masayuki,Ohashi, Kousuke
experimental part, p. 2471 - 2478 (2011/04/26)
Several novel 1,3-oxazinane and oxazolidine derivatives were obtained from the corresponding N-benzyl-2-(2-hydroxyethyl)-and N-benzyl-2-(hydroxymethyl) piperidines via electrochemical oxidation. The reactions were carried out in methanol under basic conditions. The yields of the cyclic products were significantly improved using catalytic amounts of iodide ions, which presumably act as effective electron carriers in the two-electron oxidation process. The Japan Institute of Heterocyclic Chemistry.
Novel piperidine σ receptor ligands as potential antipsychotic drugs
Gilligan,Cain,Christos,Cook,Drummond,Johnson,Kergaye,McElroy,Rohrbach,Schmidt,Tam
, p. 4344 - 4361 (2007/10/02)
σ receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine σ ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for σ sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these σ ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.
Cycloaddition of 2,3,4,5-Tetrahydropyridine N-Oxide to Vinyl Ethers. Enantioselective Synthesis of 2-(N-Benzylpiperidin-2-yl)ethanol
Carruthers, William,Coggins, Peter,Weston, John B.
, p. 117 - 118 (2007/10/02)
The title compound has been obtained in high optical purity by cycloaddition of 2,3,4,5-tetrahydropyridine N-oxide and (R)-2,2-dimethyl-1-phenylpropyl vinyl ether followed by N-benzylation and reduction of the salt with lithium aluminium hydride.
CYCLOADDITION OF 2,3,4,5-TETRAHYDROPYRIDINE N-OXIDE TO ISOBUTYL VINYL ETHER AND ALLYL ALCOHOL; METHYL 2-FORMYLMETHYLPIPERIDINE-1-CARBOXYLATE
Carruthers, William,Moses, Roger C.
, p. 2251 - 2254 (2007/10/02)
2,3,4,5-Tetrahydropyridine N-oxide undergoes cycloaddition with isobutyl vinyl ether and allyl alcohol to give the hexahydroisoxazolopyridines (3) and (4).In model experiments these were converted into methyl 2-formylmethylpiperidine-1-carboxylate (9).
