766-61-0Relevant articles and documents
Nickel-catalyzed synthesis of stereochemically defined enamides via Bi- and tricomponent coupling reaction
Liu,De Nisi,Cerveri,Monari,Bandini
supporting information, p. 5034 - 5037 (2017/11/06)
The stereoselective synthesis of (E)-trisubstituted tertiary enamides is documented via site-selective Ni-catalyzed β-arylation of allenamides with boronic acids in high yields (up to 89%). The nucleophilic character of the "organo-Ni" intermediates is further exploited to implement a one-pot tricomponent procedure involving the final allylation of aldehydes (yields up to 93%). Mechanistic insights and efficiency on a gram scale process were also documented.
Copper nanoparticle mediated 'click glycosylation' for the synthesis of fluorinated triazole derivatives
Al-Duaij, Omar K.,Guesmi, Ahlem,Hamadi, Naoufel B.
, p. 374 - 379 (2016/09/09)
Background: The synthesis of triazole derivatives is a major interest among synthetic organic chemists. Indeed, triazole derivatives, especially containing fluorine atom, present wide applications in the field of science materials. In this aim, we have developed this work to propose a new route for the synthesis of fluorinated triazole derivatives. Methods: Various acetylenic compounds derived from ?- and ?-lactam on reaction with using ?- and ?-lactam and sodium azide in the presence of 5 mol% of copper nanoparticles in water to offered triazole derivatives. Results: Replacement of CH3 CN with H2O as a solvent, for the reaction catalyzed by CuNPs to produce fluorinated triazole, was finished within 1 h in 90% yield. Conclusion: A simple and efficient protocol for the synthesis of 1,2,3-triazole derivatives using 5 % of copper nanoparticles was developed.
Isoxazoline, isoxazole, and oxadiazole derivatives as M1 muscarinic acetylcholine receptor agonists
Muthusamy, Selvaraj,Lee, Soo Min,Huang, Minghua,Cho, Nam-Chul,Nam, Ghilsoo,Pae, Ae Nim,Rhim, Hyewhon,Keum, Gyochang,Choi, Kyung Il
supporting information, p. 1020 - 1028 (2016/07/15)
Insertion of a methylene linker between the 2-pyrrolidinone substituent and the isoxazoline core of the lead compound 1 previously reported resulted in the loss of its agonistic activity. One exception was the compound 6f having oxadiazole core and 2-azabicyclo[2.2.1]heptane substituent. Of the two isomers of 6f, exo-isomer (EC50 0.013 μM) was five-to six-fold more effective than endo-isomer (EC50 0.30 μM), and ca. two-fold active than the mother compound 1 (EC50 0.031 μM) in stimulating the M1 mAChR. Both isomers were moderately selective agonists for M1 mAChR over the rest four subtypes, and it could be explained by docking study on active conformation allosteric binding sites of M1-M5 mAChRs and calculating their binding energies.
Design, synthesis, and action of oxotremorine-related hybrid-type allosteric modulators of muscarinic acetylcholine receptors
Disingrini, Teresa,Muth, Mathias,Dallanoce, Clelia,Barocelli, Elisabetta,Bertoni, Simona,Kellershohn, Kerstin,Mohr, Klaus,De Amici, Marco,Holzgrabe, Ulrike
, p. 366 - 372 (2007/10/03)
A novel series of muscarinic receptor ligands of the hexamethonio-type was prepared which contained, on one side, the phthalimidopropane or 1,8-naphthalimido-2,2-dimethylpropane moiety typical for subtype selective allosteric antagonists and, on the other, the acetylenic fragment typical for the nonselective orthosteric muscarinic agonists oxotremorine, oxotremorine-M, and related muscarinic agonists. Binding experiments in M2 receptors using [3H]N-methylscopolamine as an orthosteric probe proved an allosteric action of both groups of hybrids, 7a-10a and 8b-10b. The difference in activity between a-group and b-group hybrids corresponded with the activity difference between the allosteric parent compounds. In M1-M 3 muscarinic isolated organ preparations, most of the hybrids behaved as subtype selective antagonists. [35S]GTPγS binding assays using human M2 receptors overexpressed in CHO cells revealed that a weak intrinsic efficacy was preserved in 8b-10b. Thus, attaching muscarinic allosteric antagonist moieties to orthosteric muscarinic agonists may lead to hybrid compounds in which functions of both components are mixed.
On the base-induced isomerization of cyclic propargylamides to cyclic allenamides
Fenández, Israel,Monterde, María I.,Plumet, Joaquín
, p. 6029 - 6031 (2007/10/03)
The reaction of lactams 4 (n = 1-5) with propargyl bromide affords propargylamides or allenylamides depending on the ring-size. Theoretical calculations support the dependence of the extension of the isomerization on the ring-size.
Pyrrolidinone derivatives, their preparation and pharmaceutical composition comprising the same
-
, (2008/06/13)
The present invention relates to substituted pyrrolidinone compounds of formula 1, wherein n is 0 or 1; Aza is a heterocycle optionally substituted with C1-4 alkyl, or C1-4 alkyl substituted with a heterocycle, which represents a saturated or unsaturated five- or six-membered ring having nitrogen(s) as a heteroatom, which are muscarinic acetylcholine receptor agonists and useful as nootropics and therapeutic agents for cerebral neural diseases such as Alzheimer's disease; and pharmaceutically acceptable salts thereof; processes for the preparation thereof; and pharmaceutical compositions comprising these compounds or salts.
Efficient preparations of novel ynamides and allenamides
Wei, Lin-Li,Mulder, Jason A.,Xiong, Hui,Zificsak, Craig A.,Douglas, Christopher J.,Hsung, Richard P.
, p. 459 - 466 (2007/10/03)
Practical syntheses of a series of novel ynamides and allenamides are described here. While a base-induced isomerization protocol of propargyl amides leads to an array of chiral and achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.
A novel synthesis of 2,3-dihydro-7(1H)-indolizinones
Gravestock, David,Peirson, Ian G.
, p. 3497 - 3500 (2007/10/03)
Intramolecular coupling reactions of enynes 2-[1-(2-propynyl)tetrahydro- 2H-pyrrol-2-yliden]acetonitrile (10) and ethyl 2-[1-(2-propynyl)tetrahydro- 2H-pyrrol-2-ylidene]acetate (11), using 9-BBN, catecholborane and alkaline silver nitrate, afforded the 2,3-dihydro-7(1H)-indolizinones, 7-oxo-1,2,3,7- tetrahydro-8-indolizinecarbonitrile (5) and ethyl 7-oxo-1,2,3,7-tetrahydro-8- indolizinecarboxylate (6), respectively. (C) 2000 Elsevier Science Ltd.
Inverse demand [4+2] cycloaddition reactions of allenamides: Reactivity scopes of an electron deficient variant of allenamines
Wei, Lin-Li,Xiong, Hui,Douglas, Christopher J.,Hsung, Richard P.
, p. 6903 - 6907 (2007/10/03)
The synthesis and reactivity of a series of new allenamides are described. These electron deficient variants of allenamines are more stable than allenamines but possess comparable reactivity. Particularly, oxazolidinone and imidazolidinone substituted allenamides undergo efficient inverse demand [4+2] cycloaddition reactions with heterodienes, leading to unique pyranyl heterocycles. The reactivity differences between various allenamides containing different substitution patterns around the nitrogen atom are illustrated.
β-Lactam Analogues of Oxotremorine. 3- and 4-Methyl-Substituted 2-Azetidinones
Nilsson, Bjoern M.,Ringdahl, Bjoern,Hacksell, Uli
, p. 580 - 584 (2007/10/02)
Four β-lactam analogues (8-11) of oxotremorine were synthesized and assayed for muscarinic and antimuscarinic activity on the isolated guinea pig ileum.The pharmacological results were compared with those obtained previously with the β-lactam analogue 7 and the 3-, 4-, and 5-methyl-substituted 2-pyrrolidones 2-6.The new compounds were less potent than the corresponding 2-pyrrolidones, regardless of whether they showed agonist (10 and 11), partial agonist (8), or antagonist properties (9) in the ileum assay.The agonists 10 and 11 were about 200-fold less potent than7.Compounds 8-11 also were less potent than the similarly substituted 2-pyrrolidones in inhibiting the binding of the muscarinic antagonist (-)--N-methylscopolamine in homogenates of the rat cerebral cortex.
