- Bioactivity-guided synthesis of tropine derivatives as new agonists for melatonin receptors
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Twenty-three tropine derivatives as new melatonin receptor (MT1 and MT2) agonists were synthesized and evaluated on HEK293 cells in vitro. Derivatives 1f, 1i, 1j, 1m-1s and 1t exhibited increased agonisting activities on MT1 and MT2 receptors compared to the substrate tropine. Particularly, compound 1r showed significant agonistic activities on MT1 and MT2 receptors with EC50 values of 0.20 and 0.24 mM, respectively. The preliminary structure-activity relationships (SARs) of tropine derivatives were summarized for further investigation on melatonin receptor agonists.
- Yin, Xiu-Juan,Geng, Chang-An,Huang, Xiao-Yan,Chen, Hao,Ma, Yun-Bao,Chen, Xing-Long,Sun, Chang-Li,Yang, Tong-Hua,Zhou, Jun,Zhang, Xue-Mei,Chen, Ji-Jun
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Read Online
- N-Methylation of Amines with Methanol at Room Temperature
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N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups. (Chemical Presented)
- Tsarev, Vasily N.,Morioka, Yuna,Caner, Joaquim,Wang, Qing,Ushimaru, Richiro,Kudo, Akihiko,Naka, Hiroshi,Saito, Susumu
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supporting information
p. 2530 - 2533
(2015/05/27)
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- METHOD OF PRODUCING TERTIARY AMINE OR TERTIARY AMINE DERIVATIVE
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PROBLEM TO BE SOLVED: To provide a method of producing tertiary amine or tertiary amine derivative with high selectivity. SOLUTION: In the method of producing tertiary amine or tertiary amine derivative, a reaction system including: an organic chemical raw material containing at least one kind of group selected from -NH2, -NH2 HCl, >NH and >NH HCl, a nitrogen atom contained in the group bounding to a carbon atom; aliphatic alcohol having 1 to 20 carbon atoms; and a catalyst where a carrier containing titanium oxide carries a silver component (metal silver or silver compound), is irradiated with light, and the group in the organic compound raw material is converted to -NR02 or >NR0, ( R0 is an aliphatic hydrocarbon group having 1 to 20 carbon atoms derived from the aliphatic alcohol). The percentage content of the silver in the catalyst is 0.5 to 10 mass% with respect to the titanium oxide. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0066; 0073; 0079
(2018/10/31)
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- A facile synthesis of enantiopure 7-benzyloxycarbonyl-7-azabicyclo [2.2.1]heptane-2-carboxylic acid
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An efficient procedure for the preparation of enantiopure 7-benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carboxylic acids is described.
- Chiou, Wen-Hua,Chiang, Yu-Min,Chen, Guei-Tang
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- CRYSTALLINE ATROPINE SULFATE
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The present invention relates to crystalline polymorph form of Atropine sulfate and process for the preparation thereof.
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Page/Page column 4
(2014/07/21)
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- Total synthesis of tropinone using 1,3-dipolar cycloaddition of cyclic azomethine ylide and phenyl vinyl sulfone as the key step
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Total synthesis of tropinone from the readily available piperidone 2 is described. The rapid assembly of the tropane skeleton was achieved by 1,3-dipolar cycloaddition of cyclic azomethine ylide 3 to phenyl vinyl sulfone.
- Laha, Joydev K.
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experimental part
p. 254 - 256
(2010/09/18)
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- Productive chloroarene C-Cl bond activation: Palladium/phosphine-catalyzed methods for oxidation of alcohols and hydrodechlorination of chloroarenes
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The palladium/phosphine-catalyzed productive chloroarene C-Cl bond activation provides general, efficient, and functional group friendly methods for the selective oxidation of alcohols and the hydrodechlorination of chloroarenes.
- Bei, Xiaohong,Hagemeyer, Alfred,Volpe, Anthony,Saxton, Robert,Turner, Howard,Guram, Anil S.
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p. 8626 - 8633
(2007/10/03)
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- Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes
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o-Iodoxybenzoic acid (IBX), a readily available hypervalent iodine(V) reagent, was found to be highly effective in carrying out oxidations adjacent to carbonyl functionalities (to form α, β-unsaturated carbonyl compounds) and at benzylic and related carbon centers (to form conjugated aromatic carbonyl systems). Mechanistic investigations led to the conclusion that these new reactions are initiated by single electron transfer (SET) from the substrate to IBX to form a radical cation which reacts further to give the final products. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates, elevating the status of this reagent to that of a highly useful and chemoselective oxidant.
- Nicolaou,Montagnon,Baran,Zhong
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p. 2245 - 2258
(2007/10/03)
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- Novel asymmetric dealkoxycarbonylation of 3-oxo-8-azabicyclo[3.2.1]- octane-2,4-dicarboxylates using porcine liver esterase: A new route to (-)- anhydroecgonine methyl ester
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The porcine liver esterase-catalyzed dealkoxycarbonylation of 8-benzyl- 3-oxo-8-azabicyclo[3.2.1]octane-2,4-dicarboxylates (4) was found to give high enantiomeric excess of the desymmetrized keto ester (5). This novel dealkoxylcarbonylation opened a new route to the asymmetric synthesis of (1R)-cocaine related radiopharmaceuticals such as (1R)-β-CIT, for diagnosis of Parkinson's disease.
- Node, Manabu,Nakamura, Soichi,Nakamura, Daisaku,Katoh, Takahiro,Nishide, Kiyoharu
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p. 5357 - 5360
(2007/10/03)
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- Efficient generation and [3+2] cycloaddition of cyclic azomethine ylides: A general synthetic route to x-azabicyclo (m.2.1) alkane framework
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An efficient method of cyclic azomethine ylide generation and their application in synthesizing x-azabicylo (m.2.1) alkanes has been described.
- Pandey,Lakshmaiah,Ghatak
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p. 7301 - 7304
(2007/10/02)
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- SYMMETRIE-ENHANCED REMOTE DICARBANION ANNULATIONS FOR LATENT CYCLOALKENONES: APPLICATION TO ALKALOIDS AND TERPENES
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Fuctionalized 1,n-dicarbanions (n = 4,5,6) react with α,α'-methallyl dihalides to produce n+3 substituted α-methylenecycloalkanes that are synthetic equivalents of two differentiable cycloalkenones.
- Lansbury, Peter T.,Spagnuolo, Ciro J.,Grimm, Erich L.
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p. 3965 - 3968
(2007/10/02)
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- Biomimetic Synthesis of Tropinone by Oxidation of Hygrine with Mercury(II) Acetate
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Tropinone and (E)-2,1'-dehydrohygrine were obtained by refluxing a solution of hygrine in dilute acetic acid with mercury(II) acetate.
- Leete, Edward,Kim, Sung Hoon
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p. 1899 - 1900
(2007/10/02)
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- Oxidative Cleavage of Ketoximes with Iodosobenzene Diacetate
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Hypervalent iodine oxidation of ketoximes (1) using iodosobenzene diacetate leads to cleavage of 1 with the formation of corresponding ketones (2) under neutral conditions in good yields.The scope and limitations of the reaction are discussed as well as the mechanism.
- Moriarty, Robert M.,Prakash, Om,Vavilikolanu, Pushra R.
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p. 1247 - 1254
(2007/10/02)
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- Studies on the neuroleptic benzamides. III - Synthesis and antidopaminergic properties of new 3-nortropane derivatives
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Various benzamides prepared from 4-alkoxy pyrimidine 5-carboxylic acids and 3-amino nortropane derivatives have been tested for their potential antipsychotic activity. Two compounds exhibited pharamacological activity equivalent to that of haloperidol but had lower toxicity and lower potency to induced catalepsy. Antidopaminergic activity is observed mainly in compounds in which the nortropane ring is substituted in the equatorial position, having a benzyl substituent on the basic nitrogen. The influence of electron attractor or donor substituents carried by the benzyl ring has been evaluated. Some aspects of structure-activity relationships are discussed.
- Dostert,Imbert,Langlois,et al.
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p. 105 - 110
(2007/10/02)
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- Analysis and stability of atropine sulfate and scopolamine hydrobromide. 1. Qualitative detection of alkaloids in the presence of their decomposition products. 73. Contribution to the problem of the use of plastic receptacles for liquid pharmaceuticals
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The authors deal with the qualitative determination of tropane alkaloid salts (atropine sulphate and scopolamine hydrobromide) in aqueous solutions in the presence of their decomposition products using thin-layer chromatography. Aqueous solutions of these tropane alkaloid salts were tested for stability after storage in glass and polyethylene containers under various conditions (pH value, temperature, ultra-violet irradiation, oxidative effects). Besides tropine, apoatropine, alpha- and beta-belladonine, further decomposition products showing a basic reaction (and in part not yet identified) were detected. The stability of solid atropine sulphate was studied by means of differential thermal analysis and mass spectrometry.
- Jira,Pohloudek-Fabini
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p. 645 - 649
(2007/10/02)
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- REDUCTIVE TRANSFORMATION OF A HYDROXYIODOKETONE OF 8-AZABICYCLOOCTANE INTO 7-AZABICYCLOHEPTANE WITH LITHIUM ALUMINIUM HYDRIDE
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1α,4β-Diodo-2α-acetoxytropan-3-one (2) and 1α-iodo-2α-acetoxytropan-3-one (3), which comprise 64percent of products emerging from the lead tetraacetate oxidation of tropan-3α-ol in presence of iodine, were subjected to lithium aluminium hydride reduction.The expected 2.3-dihydroxytropane was not obtained.Instead, a diol which was not prone to periodate oxidation, containing one primary and one secondary alkoholic groups was obtained.It was assigned the 1-hydroxymethyl-2α-hydroxy-7-methyl-7-azabicycloheptane structure (8), on the basis of spectroscopic evidences (ir, nmr and mass spectrometry) and some chemical transformations heptane (12)>.The reaction is understood as an initial β-elimination process, triggered by the delivery of hydride ion to the carbonyl function in the sequence 3 21 22, yielding a highly reactive enolate aldehyde (22) which is prone to an immediate internal aldol condensation (22) (23) (24), affording the observed diol (8) on further reduction of the a aldehydic group by LiALH4.The reductive deiodination of (3) into 2α-acetoxytropine (2b) or into 2α-hydroxytropan-3-one (25) was smoothly achieved by means of hydrogenation over Raney Nickel on mild basic conditions.
- Sarel, Shalom,Dykman, Edmund
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p. 719 - 734
(2007/10/02)
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