39858-70-3Relevant academic research and scientific papers
Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds
Cox, Joshua B.,Jackson, Amy C.,Lambert, Kyle M.,Liu, Lin,Wiberg, Kenneth B.,Wood, John L.,Yruegas, Sam
, p. 9757 - 9766 (2020)
The development of a concise total synthesis of (±)-phyllantidine (1), a member of the securinega family of alkaloids containing an unusual oxazabicyclo[3.3.1]nonane core, is described. The synthesis employs a unique synthetic strategy featuring the ring
Kinetic Patterns of Condensation of Alkyl- and Cycloalkylcyclopentanones with Dihydric Alcohols in the Presence of Polyoxomolybdate Modified with Oxides of Rare-Earth Elements
Alimardanov, Kh. M.,Velieva,Dadashova
, p. 1882 - 1889 (2019/02/24)
The results of condensation of C5–C7 alkyl- and cycloalkyl-substituted cyclopentanones with diatomic vicinal alcohols in the presence of polyoxomolybdate modified with gadolinium oxide are considered. Kinetic patterns are investigated and a kinetic model of the process is proposed. It was established that alkyl- and cycloalkyl derivatives of dioxaspironone are formed directly by two parallel-consecutive routes and through the stages of the preparation of the corresponding hemiacetal. The ratio of the rate constants of these routes depends on the composition and structure of the starting ketones and diols.
The identification of 7-[(R)-2-((1S,2S)-2-benzyloxycyclopentylamino)-1- hydroxyethyl]-4-hydroxybenzothiazolone as an inhaled long-acting β2-adrenoceptor agonist
Arnold, Nicola,Beattie, David,Bradley, Michelle,Brearley, Andrew,Brown, Lyndon,Charlton, Steven J.,Fairhurst, Robin A.,Farr, David,Fozard, John,Fullerton, Joe,Gosling, Martin,Hatto, Julia,Janus, Diana,Jones, Darryl,Jordan, Lynne,Lewis, Christine,Maas, Janet,McCarthy, Clive,Mercer, Mark,Oakman, Helen,Press, Neil,Profit, Rachel,Schuerch, Friedrich,Sykes, David,Taylor, Roger J.,Trifilieff, Alexandre,Tuffnell, Andrew
, p. 4341 - 4347 (2014/10/15)
The optimisation of two series of 4-hydroxybenzothiazolone derived β2-adrenoceptor agonists, bearing α-substituted cyclopentyl and β-phenethyl amino-substituents, as inhaled long-acting bronchodilators is described. Analogues were selected for synthesis using a lipophilicity based hypothesis to achieve the targeted rapid onset of action in combination with a long duration of action. The profiling of the two series led to identification of the α-substituted cyclopentyl analogue 2 as the optimal compound with a comparable profile to the inhaled once-daily long-acting β2-adrenoceptor agonist indacaterol. On the basis of these data 2 was promoted as the backup development candidate to indacaterol from the Novartis LABA project.
BENZOTHIAZOLE DERIVATIVES HAVING BETA-2-ADRENORECEPTOR AGONIST ACTIVITY
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Page 36, (2008/06/13)
Compounds of Formula (I) in free or salt or solvate form, wherein X has the meaning indicated in the specification, are useful for treating conditions that are prevented or alleviated by activation of the ?2-adrenoreceptor. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.
EPC syntheses and structure-activity relationships of hypoglycaemic semicyclic amidines
Hartmann, Susanne,Ullrich, Susanne,Hupfer, Charlotte,Frahm, August W.
, p. 377 - 392 (2007/10/03)
A series of homochiral sterically hindered mono- and bicyclic amidines was prepared as hypoglycaemic agents by lethargic reaction of O- methylcaprolactim and 3-ethoxy-2-azabicyclo[2.2.2]oct-2-ene, respectively, with homochiral cis-2-substituted cyclopentane amines provided by asymmetrical reductive amination of racemic 2-substituted cyclopentanones. All compounds, except the cyclohexylmethyl-isoquinuclidone derivative which inhibited secretion at 100 μM, significantly stimulated insulin secretion 2- 8-fold at 10 μM and 100 μM in INS-1 cells. The most potent activator was the 2-cyclopentyl-substituted caprolactam derivative 5e. The stimulatory effects on secretion increased with rising steric hindrance of both the amidine α-carbon and the bicyclic amidine moiety itself. Enantiomeric discrimination was observed for the 2-[(cis-2-bulkysubstituted cyclopentyl)imino]hexahydroazepine halides 5e and 5f and for the 3-[(cis-2- substituted cyclopentyl)imino]-2-azabicyclo[2.2.2]octane halides 6a and 6c. The amidines depolarized INS-1 cells and generated action potentials, accompanied by a decrease of membrane conductance. Simultaneously [Ca2+](i) increased, probably due to Ca2+-entry through voltage-dependent Ca2+- channels. At high concentrations, where inhibition of secretion was observed, [Ca2+](i) still rose upon application of the amidines, indicating an additional inhibitory pathway downstream to the elevation of [Ca2+](i). Even at high concentrations (100 μM), the amidines had no toxic effects on insulin secreting INS-1 cells. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
Catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones
Abbasov,Alimardanov,Suleimanova
, p. 621 - 626 (2007/10/03)
Pilot-plant syntheses of alkyl and cycloalkylcyclanones and their subsequent liquid-phase oxidation into lactones are described. Characteristics of resulting intermediates and target products are reported.
Free Radical Ring Expansion of Fused-Methylenecyclobutanes
Zhang, Wei,Dowd, Paul
, p. 8539 - 8542 (2007/10/02)
Fused methylenecyclobutanes comprise a new free radical ring expansion system leading to cis-fused methylenecycloheptanes.
Free-Radical Ring Expansion of Fused Cyclobutanones: Stereospecific Construction of 5,7-, 6,7-, 7,7-, 8,7-, and 5,8-Cis-Fused Bicyclic Systems
Dowd, Paul,Zhang, Wei
, p. 7163 - 7171 (2007/10/02)
A new method of appending seven- and eight-membered rings to cycloalkenes is described.Treatment of selected alkene precursors with an ω-bromoalkyl ketene or a keteniminium salt leads to haloalkyl cyclobutanone formation.Tri-n-butyltin hydride promoted ring expansion then yields the annulated product.Since the initial cyclobutanone is cis fused, the final product is also produced stereospecifically with a cis ring fusion.
