- Structure activity relationship and modeling studies of inhibitors of lysine specific demethylase 1
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Post-translational modifications of histone play important roles in gene transcription. Aberrant methylation of histone lysine sidechains have been often found in cancer. Lysine specific demethylase 1 (LSD1), which can demethylate histone H3 lysine 4 (H3K4) and other proteins, has recently been found to be a drug target for acute myeloid leukemia. To understand structure activity/selectivity relationships of LSD1 inhibitors, several series of cyclopropylamine and related compounds were synthesized and tested for their activities against LSD1 and related monoamine oxidase (MAO) A and B. Several cyclopropylamine containing compounds were found to be highly potent and selective inhibitors of LSD1. A novel series cyclopropylimine compounds also exhibited strong inhibitory activity against LSD1.Structure activity relationships (SAR) of these compounds are discussed. Docking studies were performed to provide possible binding models of a representative compound in LSD1 and MAO-A. Moreover, these modeling studies can rationalize the observed SARs and selectivity.
- Zhou, Chao,Wu, Fangrui,Lu, Lianghao,Wei, Liping,Pai, Eric,Yao, Yuan,Song, Yongcheng
-
-
- Synthesis and in vitro evaluation of novel N-cycloalkylcarbamates as potential cholinesterase inhibitors
-
Abstract: This present paper describes the preparation and characterization of a series of O-substituted N-cycloalkylcarbamate derivatives. These compounds were tested as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). All studied carbamates exhibited moderate inhibitory activity of both cholinesterases with values of IC50 in the range of 36.1–78.6?μM for AChE and 9.8–215.4?μM for BChE, respectively. These values are comparable with those values of inhibition obtained with the established drug rivastigmine. The cytotoxicity of all carbamates was evaluated using standard in vitro test with Jurkat cells. Many of the studied carbamates can be considered as promising compounds for potential medicinal applications with regard to their inhibitory activity as well as negligible cytotoxicity.
- Horáková, Eva,Drabina, Pavel,Br??ková, Lenka,?těpánková, ?árka,Vor?áková, Katarína,Sedlák, Milo?
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p. 2143 - 2153
(2017/09/25)
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- Synthesis, characterization and in vitro evaluation of substituted N-(2-phenylcyclopropyl)carbamates as acetyl- and butyrylcholinesterase inhibitors
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A serie of O-substituted N-2-phenylcyclopropylcarbamates was prepared and characterized. These carbamates were tested as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). It was found, that these compounds exhibit moderate inhibition activity with values of IC50 in the range of 54.8–94.4 μM (for AChE) and up to 5.8 μM (for BChE). The AChE/BChE selectivity for each carbamate was calculated. These values varied from 0.50 to 9.46, two carbamate derivatives inhibited only AChE selectively. The most promising derivative was prepared in all optically pure forms (four isomers). It was found that individual stereoisomers differed only slightly in the inhibition ability. The cytotoxicity of all carbamates was evaluated using the standard in vitro test with Jurkat cells. With regard to their inhibition activity and cytotoxicity as well as easy preparation, O-substituted N-2-phenylcyclopropylcarbamates can be considered as promising compounds for potential medicinal applications.
- Horáková, Eva,Drabina, Pavel,Bro?, B?etislav,?těpánková, ?árka,Vor?áková, Katarína,Královec, Karel,Havelek, Radim,Sedlák, Milo?
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p. 173 - 179
(2016/12/16)
-
- Nickel-Catalyzed Reductive Carboxylation of Cyclopropyl Motifs with Carbon Dioxide
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A nickel-catalyzed reductive carboxylation technique for the synthesis of cyclopropanecarboxylic acids has been developed. This user-friendly and mild transformation operates at atmospheric pressure of carbon dioxide and utilizes either organic halides or alkene precursors, thus representing the first example of catalytic reductive carboxylation of secondary counterparts lacking adjacent π-components.
- Moragas, Toni,Martin, Ruben
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p. 2816 - 2822
(2016/08/26)
-
- The synergistic effect of copper chromite spinel nanoparticles (CuCr2O4) and basic ionic liquid on the synthesis of cyclopropanecarboxylic acids
-
Abstract: An efficient synthesis of cyclopropanecarboxylic acids using copper chromite spinel nanoparticles and basic ionic liquid is described. In this study, a relatively simple method starting with trans-cinnamic acid for the synthesis of (±)-trans-2-phenylcyclopropanecarboxylic acid, a key intermediate in the synthesis of tranylcypromine sulfate as an active pharmaceutical ingredient, was employed. Using a combination of basic ionic liquid [Bmim]OH and copper chromite spinel nanoparticles as a catalytic system, the best results were obtained in THF as a polar solvent. This method is a useful alternative to other approaches described in the literature. The use of commercially available chemicals, decreased environmental hazards, with no need for the separation of stereoisomers, and consequently a reduced number of overall steps, are the advantages of this approach that make it an appropriate choice at an increased scale. Graphical Abstract: [Figure not available: see fulltext.]
- Ghasemi, Mohammad Hadi,Kowsari, Elaheh
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p. 7963 - 7975
(2016/11/25)
-
- Discovery of a Novel Inhibitor of Histone Lysine-Specific Demethylase 1A (KDM1A/LSD1) as Orally Active Antitumor Agent
-
We report the stereoselective synthesis and biological activity of a novel series of tranylcypromine (TCPA) derivatives (14a-k, 15, 16), potent inhibitors of KDM1A. The new compounds strongly inhibit the clonogenic potential of acute leukemia cell lines. In particular three molecules (14d, 14e, and 14g) showing selectivity versus MAO A and remarkably inhibiting colony formation in THP-1 human leukemia cells, were assessed in mouse for their preliminary pharmacokinetic. 14d and 14e were further tested in vivo in a murine acute promyelocytic leukemia model, resulting 14d the most effective. Its two enantiomers were synthesized: the (1S,2R) enantiomer 15 showed higher activity than its (1R,2S) analogue 16, in both biochemical and cellular assays. Compound 15 exhibited in vivo efficacy after oral administration, determining a 62% increased survival in mouse leukemia model with evidence of KDM1A inhibition. The biological profile of compound 15 supports its further investigation as a cancer therapeutic.
- Vianello, Paola,Botrugno, Oronza A.,Cappa, Anna,Dal Zuffo, Roberto,Dessanti, Paola,Mai, Antonello,Marrocco, Biagina,Mattevi, Andrea,Meroni, Giuseppe,Minucci, Saverio,Stazi, Giulia,Thaler, Florian,Trifiró, Paolo,Valente, Sergio,Villa, Manuela,Varasi, Mario,Mercurio, Ciro
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p. 1501 - 1517
(2016/03/08)
-
- The influence of cosolvent concentration on enzymatic kinetic resolution of trans-2-phenyl-cyclopropane-1-carboxylic acid derivatives
-
A method to improve the enantioselectivity of lipase-catalyzed kinetic resolution (KR) of trans-2-phenyl-cyclopropane-1-carboxylic acid derivatives in water-acetone solution is presented. Two different approaches were compared: enzyme-catalyzed esterification and enzymatic hydrolysis of the target ester. A substantial influence of enzyme type, ethoxy group donor, and solvent on conversion and enantioselectivity of the enzymatic esterification was noted. While enzymatic esterification proceeds with poor enantioselectivity, the hydrolysis of target ester proceeds efficiently. Studies on the influence of cosolvent used for the enzymatic hydrolysis reaction showed that kinetic resolution can be performed in acetone and water buffer mixture predominantly containing organic solvent. Any change in organic solvent content resulted in a substantial decrease in enantioselectivity from almost E = 150 to less than 5.
- Wi?niewska, Catalina,Koszelewski, Dominik,Zysk, Ma?gorzata,Ostaszewski, Ryszard
-
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- Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: Facile access to spiro 3,3′-cyclopropyl oxindoles
-
The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C-H bonds is described. Various spiro 3,3′-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.
- Ladd, Carolyn L.,Sustac Roman, Daniela,Charette, André B.
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supporting information
p. 1350 - 1353
(2013/05/09)
-
- SERINE/THREONINE PAK1 INHIBITORS
-
Compounds having the formula I wherein A, Z, R1a, R1b, R2, R3, R4, R5, R6, R7, R9, R10, Ra, Rb and n are as defined herein are inhibitors of PAK1. Also disclosed are compositions and methods for treating cancer and hyperproliferative disorders.
- -
-
-
- (HETERO)ARYL CYCLOPROPYLAMINE COMPOUNDS AS LSD1 INHIBITORS
-
The invention relates to (hetero)aryl cyclopropylamine compounds, including particularly the compounds of formula (I) as described and defined herein, and their use in therapy, including, e.g., in the treatment or prevention of cancer, a neurological disease or condition, or a viral infection.
- -
-
Page/Page column 140; 152; 153
(2013/05/09)
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- Probes for narcotic receptor mediated phenomena. 41. Unusual inverse μ-agonists and potent μ-opioid antagonists by modification of the N-substituent in enantiomeric 5-(3-hydroxyphenyl)morphans
-
Conformational restraint in the N-substituent of enantiomeric 5-(3-hydroxyphenyl)morphans was conferred by the addition of a cyclopropane ring or a double bond. All of the possible enantiomers and isomers of the N-substituted compounds were synthesized. Opioid receptor binding assays indicated that some of them had about 20-fold higher μ-affinity than the compound with an N-phenylpropyl substituent (Ki = 2-450 nM for the examined compounds with various N-substituents). Most of the compounds acted unusually as inverse agonists in the [35S]GTP-γ-S functional binding assay using nondependent cells that stably express the cloned human μ-opioid receptor. Two of the N-substituted compounds with a cyclopropane ring were very potent μ-opioid antagonists ((+)-29, Ke = 0.17 and (-)-30, Ke =0.3) in the [35S]GTP-γ-S functional binding assay. By comparison of the geometry-optimized structures of the newly synthesized compounds, an attempt was made to rationalize their μ-opioid receptor affinity in terms of the spatial position of N-substituents. This article not subject to U.S. Copyright. Published 2011 by the American Chemical Society.
- Cheng, Kejun,Lee, Yong Sok,Rothman, Richard B.,Dersch, Christina M.,Bittman, Ross W.,Jacobson, Arthur E.,Rice, Kenner C.
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experimental part
p. 957 - 969
(2011/04/24)
-
- Biochemical, structural, and biological evaluation of tranylcypromine derivatives as inhibitors of histone demethylases LSD1 and LSD2
-
LSD1 and LSD2 histone demethylases are implicated in a number of physiological and pathological processes, ranging from tumorigenesis to herpes virus infection. A comprehensive structural, biochemical, and cellular study is presented here to probe the potential of these enzymes for epigenetic therapies. This approach employs tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. This drug is a clinically validated antidepressant known to target monoamine oxidases A and B. These two flavoenzymes are structurally related to LSD1 and LSD2. Mechanistic and crystallographic studies of tranylcypromine inhibition reveal a lack of selectivity and differing covalent modifications of the FAD cofactor depending on the enantiomeric form. These findings are pharmacologically relevant, since tranylcypromine is currently administered as a racemic mixture. A large set of tranylcypromine analogues were synthesized and screened for inhibitory activities. We found that the common evolutionary origin of LSD and MAO enzymes, despite their unrelated functions and substrate specificities, is reflected in related ligand-binding properties. A few compounds with partial enzyme selectivity were identified. The biological activity of one of these new inhibitors was evaluated with a cellular model of acute promyelocytic leukemia chosen since its pathogenesis includes aberrant activities of several chromatin modifiers. Marked effects on cell differentiation and an unprecedented synergistic activity with antileukemia drugs were observed. These data demonstrate that these LSD1/2 inhibitors are of potential relevance for the treatment of promyelocytic leukemia and, more generally, as tools to alter chromatin state with promise of a block of tumor progression.
- Binda, Claudia,Valente, Sergio,Romanenghi, Mauro,Pilotto, Simona,Cirilli, Roberto,Karytinos, Aristotele,Ciossani, Giuseppe,Botrugno, Oronza A.,Forneris, Federico,Tardugno, Maria,Edmondson, Dale E.,Minucci, Saverio,Mattevi, Andrea,Mai, Antonello
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supporting information; experimental part
p. 6827 - 6833
(2010/07/03)
-
- Selective 5-hydroxytryptamine 2c receptor agonists derived from the lead compound tranylcypromine: Identification of drugs with antidepressant-like action
-
We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2- phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted be zene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT 2A and 5-HT2B, respectively (EC50) 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.
- Sung, Jin Cho,Jensen, Niels H.,Kurome, Toru,Kadari, Sudhakar,Manzano, Michael L.,Malberg, Jessica E.,Caldarone, Barbara,Roth, Bryan L.,Kozikowski, Alan P.
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experimental part
p. 1885 - 1902
(2009/12/07)
-
- Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors
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A series of trans-2-aryl-cyclopropylamine derived compounds were synthesized and evaluated their biological activities against DPP-IV. The structure-activity relationships (SAR) led to the discovery of novel series of DPP-IV inhibitors, having IC50 values of 100 nM with excellent selectivity over the closely related enzymes, DPP8, DPP-II and FAP. The studies identified a potent and selective DPP-IV inhibitor 24b, which exhibited the ability to both significantly inhibit plasma DPP-IV activity in rats and improve glucose tolerance in lean mice and diet induced obese mice.
- Tsai, Ting-Yueh,Hsu, Tsu,Chen, Chiung-Tong,Cheng, Jai-Hong,Yeh, Teng-Kuang,Chen, Xin,Huang, Chung-Yu,Chang, Chung-Nien,Yeh, Kai-Chia,Hsieh, Su-Huei,Chien, Chia-Hui,Chang, Yi-Wei,Huang, Chih-Hsiang,Huang, Yu-Wen,Huang, Chen-Lung,Wu, Ssu-Hui,Wang, Min-Hsien,Lu, Cheng-Tai,Chao, Yu-Sheng,Jiaang, Weir-Torn
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experimental part
p. 2388 - 2399
(2009/09/05)
-
- 5-HT2C RECEPTOR AGONISTS AS ANORECTIC AGENTS
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This invention relates to compounds which modulate receptors of the 5-HT2 family of receptors, and particularly to compounds which modulate 5-HT2C receptors. Compounds of the invention include agonists and selective agonists for the 5-HT2C receptor. Compounds of the invention include selective agonists for the 5-HT2C receptor which exhibit significantly less or no agonist activity on the 5-HT2A receptor and/or the 5-HT2B receptor. Compounds of this invention are those of Formula I and pharmaceutically acceptable salts, esters and solvates (including hydrates) wherein variables are defined in the specification hereof.
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-
Page/Page column 35; 73-74
(2008/06/13)
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- The first cyclopropanation reaction of unmasked α,β-unsaturated carboxylic acids: Direct and complete stereospecific synthesis of cyclopropanecarboxylic acids promoted by Sm/CHl3
-
Equation Presented A samarium-promoted cyclopropanation of unmasked α,β-unsaturated acids is described. This reaction can be carried out on (E)- or (Z)α,β-unsaturated carboxylic acids. In all cases the process is completely stereospecific and stereoselective. A mechanism has been proposed to explain the cyclopropanation reaction.
- Concellon, Jose M.,Rodriguez-Solla, Humberto,Simal, Carmen
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p. 2685 - 2688
(2008/02/08)
-
- Construction of a cis-Cyclopropane via Reductive Radical Decarboxylation. Enantioselective Synthesis of cis- and trans-1-Arylpiperazyl-2-phenylcyclopropanes Designed as Antidopaminergic Agents
-
(1S,2S)-, (1S,2R)-, and (1R,2S)-1-(2,4-Dimethylphenyl)piperazyl-2-phenylcyclopropane (2a, 3, and ent-3, respectively), which were designed as conformationally restricted analogues of haloperidol (1), a clinically effective antipsychotic agent, were synthe
- Yamaguchi, Kazuya,Kazuta, Yuji,Abe, Hiroshi,Matsuda, Akira,Shuto, Satoshi
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p. 9255 - 9262
(2007/10/03)
-
- Decarbonylative cross-coupling of cyclic anhydrides: Introducing stereochemistry at an sp3 carbon in the cross-coupling event
-
Treatment of cyclic anhydrides with stoichiometric amounts of nickel-neocuproine complex generates alkylcarboxylato-nickelalactones upon extrusion of CO. These metalacycles undergo cross-coupling with arylzinc reagents. The generated CO is sequestered in situ by a nickel-dppb complex. The overall sequence effects a secondary sp3(electrophile)-sp2(nucleophile) cross-coupling and allows for control of stereochemistry during the bond-forming event. Copyright
- O'Brien, Erin M.,Bercot, Eric A.,Rovis, Tomislav
-
p. 10498 - 10499
(2007/10/03)
-
- A novel approach to enantiopure cyclopropane compounds from biotransformation of nitriles
-
Rhodococcus sp. AJ270, a powerful and versatile nitrile hydratase/amidase containing microbial whole-cell system, catalyzed the enantioselective hydrolysis of both racemic trans- and cis-2-arylcyclopropanecarbonitriles to afford the corresponding amides and acids with enantiomeric excesses as high as >99%. The reaction rate and enantioselectivity observed for both nitrile hydratase and amidase were also strongly dependent upon the nature of the substituent and substitution pattern on the benzene ring of the substrates. The application of and the advantages of biotransformation of nitriles were demonstrated by preparing (1S,2R)-2-phenylcyclopropylamine and (1R,2R)-2-phenylcyclopropylmethylamine through facile and straightforward chemical manipulations of (1S,2S)-2-phenylcyclopropanecarboxylic acid and (1R,2R)-2-phenylcyclopropanecarboxamide, respectively.
- Wang, Mei-Xiang,Feng, Guo-Qiang
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p. 1575 - 1583
(2007/10/03)
-
- Catalytic cyclopropanation of alkenes using diazo compounds generated in situ. A novel route to 2-arylcyclopropylamines
-
(Equation presented) A user-friendly, one-pot process for catalytic cyclopropanation of alkenes from tosylhydrazones is described. The cyclopropanation of N-vinylphthalimide provides a new route to 2-arylcyclopropylamines, and this is exemplified in the efficient synthesis of the HIV-1 reverse transcriptase inhibitor 6.
- Aggarwal, Varinder K.,De Vicente, Javier,Bonnert, Roger V.
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p. 2785 - 2788
(2007/10/03)
-
- trans-1-[(2-phenylcyclopropyl)methyl]-4-arylpiperazines: Mixed dopamine D2/D4 receptor antagonists as potential antipsychotic agents
-
The dopaminergic receptor profile of a series of trans-1-[(2-phenylcyclopropyl)methyl]-4-arylpiperazines was examined. Aromatic substitution patterns were varied with the goal of identifying a compound having affinities for the D2 and D4 receptors in a ratio similar to that observed for the atypical neuroleptic clozapine. The compounds (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazin e (5m) and (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dimethylphenyl)piperazin e (5t) were selected for functional antagonists at D2 and D4 receptors and had a D2/D4 ratio approximating that of clozapine; they proved inactive in behavioral tests of antipsychotic activity.
- Zhang,Hodgetts,Rachwal,Zhao,Wasley,Craven,Brodbeck,Kieltyka,Hoffman,Bacolod,Girard,Tran,Thurkauf
-
p. 3923 - 3932
(2007/10/03)
-
- The effect of electrochemically formed aluminum salts on the electrochemical cyclisation of methyl cinnamate
-
Electrochemical cyclisation of methyl cinnamate with dielectrophiles has been improved by the presence of an aluminum salt which was pre-formed in situ by the electrolysis of a carboxylic acid with a sacrificial aluminum anode. High yields of three, five and six-membered cyclic products have been obtained in the reactions of methyl cinnamate with dichloromethane, 1,3- dibromopropane, and 1,4-dibromobutane.
- Guellue, Mustafa
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p. 3225 - 3228
(2007/10/03)
-
- trans-2-Aryl-N,N-dipropylcyclopropylamines: Synthesis and interactions with 5-HT(1A) receptors
-
Twelve N,N-dipropyl-substituted derivatives of trans-2- arylcyclopropylamine have been prepared and assayed for their ability to displace [3H]-8-OH-DPAT from rat brain 5-HT(1A) receptors. The new derivatives include phenyl (7a), bromo- (7b) and fluorophenyl (7c-e), 2- methoxy-5-fluorophenyl (7h), and 2-hydroxy-5-fluorophenyl (71) as well as trifluoromethylphenyl (7f) and 2,3-dichlorophenyl (7g) analogues. In the present series of compounds, electron-withdrawing substituents in the phenyl ring appear to decrease the affinity for 5-HT(1A) receptors. In contrast, electron-rich aryl groups, such as 2- or 3-thienyl (7j and 7k, respectively), provide compounds with high affinity. The additional bulk produced by the aromatic moiety in the 2-benzothienyl derivative 7i appears to be detrimental to 5-HT(1A) receptor affinity. The racemic mixtures of the interesting 7j and 7l were resolved into the enantiomers; 7j and 7l exhibited a high enantiomeric 5-HT(1A) receptor affinity ratio (75-fold and 100-fold, respectively). The enantiomers of 7j and 7l were evaluated in vivo by use of biochemical and behavioral tests in rats. Compound (1R,2R)-7j behaved as a partial agonist whereas (1R,2S)-7l appeared as an efficacious 5-HT(1A) receptor agonist, stimulating both autoreceptors and postsynaptic receptors.
- Vallgarda,Appelberg,Arvidsson,Hjorth,Svensson,Hacksell
-
p. 1485 - 1493
(2007/10/03)
-
- A novel route to cyclopropyl ketones, aldehydes, and carboxylic acids
-
Cyclopropanation of α,β-unsaturated N-methoxy-N-methyl amides provided the cyclopropyl amides in far superior yields to those obtained with the corresponding ketones. The desired ketones are then readily accessible by the addition of organometallic reagents. Access to a variety functional groups, including aldehydes and carboxylic acids, is also described.
- Rodriques, Karen E.
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p. 1275 - 1278
(2007/10/02)
-
- Semicorrin Metal Complexes as Enantioselective Catalysts. Part 2. Enantioselective Cyclopropane Formation from Olefins with Diazo Compounds Catalyzed by Chiral (Semicorrinato)copper Complexes)
-
Copper complexes of chiral, C2-symmetric semicorrin ligands were found to be efficient catalysts for the cyclopropane formation from olefins with diazo compounds.In the presence of 1 mol-percent of catalyst, alkyl diazoacetates reacted smoothly with termi
- Fritschi, Hugo,Leutenegger, Urs,Pfaltz, Andreas
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p. 1553 - 1565
(2007/10/02)
-
- LACTONIZATION OF PHENYLCYCLOPROPANECARBOXYLIC ACIDS
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The capacity of phenylcyclopropanecarboxylic acids for lactonization under the influence of mineral acids was studied.It was found that concentrated sulfuric acid at 20 deg C can give rise to lactonization only in the case where the intermediately formed carbocation is stabilized by a phenyl group.Preliminary isomerization to the corresponding unsaturated acid does not occur here.
- Sychkova, L. D.,Kharitonova, O. V.,Shabarov, Yu. S.
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p. 1298 - 1301
(2007/10/02)
-
- CARACTERE POLAIRE DU RADICAL PHENYL-2 CYCLOPROPYLE: REGIOSELECTIVE DE LA REACTION SUR LA FONCTION PEROXYACIDE
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A study of the reactivity of the 2-phenylcyclopropyl radicals obtained by thermal decomposition of 2-phenycyclopropane carboxylic peracids in benzene or cyclohexane solution is presented.It was found that these reactions led to the formation of phenylcyclopropane and its corresponding acid and not to the formation of 2-phenycyclopropanol.It appeared that the stereochemistry of the starting peracid did not influence the course of these reactions.These results led us to conclude that the 2-phenylcyclopropyl radical was very weakly nucleophilic towards the O-O peracid bond and that it reacted essentially by H-abstraction.Its low nucleophilicity which is similar to that of the phenyl radical but most likely lower than that of the bicyclo 1-heptyl radical is probably due to its pyramidal structure.
- Sorba, J.,Fossey, J.,Nedelec, J,Y.,Lefort, D.
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p. 2083 - 2088
(2007/10/02)
-