- Ligand design for alpha1 adrenoceptor subtype selective antagonists.
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Alpha1 adrenoceptors have three subtypes and drugs interacting selectively with these subtypes could be useful in the treatment of a variety of diseases. In order to gain an insight into the structural principles governing subtype selectivity, ligand base
- Bremner,Coban,Griffith,Groenewoud,Yates
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Read Online
- Copper-Catalyzed Hydroamination of Allenes: From Mechanistic Understanding to Methodology Development
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Experimental and theoretical mechanistic studies on the Cu(OTf)2-catalyzed hydroamination reaction of terminal allenes with secondary amines reveal that in situ generated cationic Cu(I) is the catalytically active species and explain the observ
- Perego, Luca Alessandro,Blieck, Rémi,Groué, Antoine,Monnier, Florian,Taillefer, Marc,Ciofini, Ilaria,Grimaud, Laurence
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Read Online
- BERBERIS ALKALOIDS. XXIX. AN INVESTIGATION OF THE ALKALOIDS OF Berberis sibirica
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The alkaloid compositions of the roots, young shoots, and leaves of Berberis sibirica have been studied, and berberine, palmatine, columbamine, berberrubine, oxyacanthine, berbamine, 8-oxoberberine, 8-oxoberrberubine, pakistanine, and pronunciferine, and
- Karimov, A.,Levkovich, M. G.,Abdullaev, N. D.,Shakirov, R.
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Read Online
- Continuous Flow Chiral Amine Racemization Applied to Continuously Recirculating Dynamic Diastereomeric Crystallizations
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A new, dynamic diastereomeric crystallization method has been developed, in which the mother liquors are continuously separated, racemized over a fixed-bed catalyst, and recirculated to the crystallizer in a resolution-racemization-recycle (R3) process. S
- Kwan, Maria H. T.,Breen, Jessica,Bowden, Martin,Conway, Louis,Crossley, Ben,Jones, Martin F.,Munday, Rachel,Pokar, Nisha P. B.,Screen, Thomas,Blacker, A. John
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p. 2458 - 2473
(2021/02/06)
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- Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity
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The use of arene/Ru/TsDPEN catalysts bearing a heterocyclic group on the TsDPEN in the asymmetric transfer hydrogenation (ATH) of dihydroisoquinolines (DHIQs) containing meta- or para-substituted aromatic groups at the 1-position results in the formation of products of high enantiomeric excess. Previously, only 1-(ortho-substituted)aryl DHIQs, or with an electron-rich fused ring gave products with high enantioselectivity; therefore, this approach solves a long-standing challenge for imine ATH.
- Barrios-Rivera, Jonathan,Xu, Yingjian,Wills, Martin
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supporting information
p. 6283 - 6287
(2020/09/02)
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- Stereoselective total synthesis of (S)- and (R)-nuciferine using benzyne chemistry
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Total syntheses of (S)- and (R)-nuciferine were accomplished through approach involving diastereoselective reaction between a chiral dihydroisoquinoline enamide and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate promoted by CsF, affording a separable mixture of diastereoisomers, which provided (S)- and (R)-nuciferine via simple and efficient transformations.
- Casagrande, Gleison A.,Deflon, Victor M.,Martins, Gabriel R.,Oliveira-Silva, Diogo,Perecim, Givago P.,Pinto, Leandro M. C.,Raminelli, Cristiano
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- Preparation method of compound 5,6-dihydroxy indoline and halogen acid salts thereof
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The invention relates to a preparation method of a compound 5,6-dihydroxy indoline and halogen acid salts thereof. Phenylethylamine SM-0 sold in the market is used as a raw material and firstly reactswith acyl chloride to obtain amide SM-1; amide SM-1 rea
- -
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Paragraph 0050-0053; 0073
(2018/04/01)
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- Total syntheses of (+)-bernumidine and its unnatural enantiomer
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Total syntheses of (+)-bernumidine and its unnatural enantiomer were accomplished through chemoenzymatic dynamic kinetic resolution and ruthenium(II)-catalyzed enantioselective hydrogenation, which provided (R)-salsolidine propyl carbamate and N-acetyl (S
- Corrêa, Bianca K.,Silva, Tamiris R.C.,Raminelli, Cristiano
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supporting information
p. 3583 - 3585
(2018/09/06)
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- Application of differential reactivity towards synthesis of lamellarin and 8-oxoprotoberberine derivatives: Study of photochemical properties of aryl-substituted benzofuran-8-oxoprotoberberines
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A unique differential reactivity between dihydroisoquinolines and 3-nitrocoumarins was observed and was exploited for the efficient construction of lamellarins and their isomeric benzofuran-8-oxoprotoberberine derivatives under acid-catalyzed or base-promoted conditions. Further, these prepared aryl-substituted benzofuran-8-oxoprotoberberine derivatives bearing electron-donating substituents on benzofuran moiety are found to be benchtop stable but light-sensitive, and can undergo oxidative ring-opening reaction to give the corresponding keto products when exposed to visible light under aerobic conditions.
- Vyasamudri, Sameer,Yang, Ding-Yah
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supporting information
p. 1092 - 1100
(2018/02/06)
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- Catechol reactivity: Synthesis of dopamine derivatives substituted at the 6-position
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Dopamine is a ubiquitous neurotransmitter essential in the proper functioning of the human body. In addition to this critical role, the catecholamine core has shown utility as a scaffold for numerous drugs and in other applications, like metal detection and adhesive materials. Substituents at the 6-position of dopamine’s catechol core can modulate its stereoelectronic properties, the acidity of its phenolic hydroxyl groups, and the overall hydrophobicity of the molecule. Herein, we report the synthesis of a series of four novel dopamine analogues substituted at the 6-position of catechol core. The1H NMR chemical shift of the aromatic proton meta to the substituent correlated strongly with the Hammett σmconstant, confirming the electronic properties of substituents.
- Rote, Jennifer C.,Malkowski, Sarah N.,Cochrane, C. Skyler,Bailey, Gabrielle E.,Brown, Noah S.,Cafiero, Mauricio,Peterson, Larryn W.
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supporting information
p. 435 - 441
(2017/02/24)
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- Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine
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Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, wit
- Khalil, Iman M.,Barker, David,Copp, Brent R.
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p. 282 - 289
(2016/01/15)
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- Enantioselective Oxidative Aerobic Dealkylation of N-Ethyl Benzylisoquinolines by Employing the Berberine Bridge Enzyme
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N-Dealkylation methods are well described for organic chemistry and the reaction is known in nature and drug metabolism; however, to our knowledge, enantioselective N-dealkylation has not been yet reported. In this study, exclusively the (S)-enantiomers o
- Gandomkar, Somayyeh,Fischereder, Eva-Maria,Schrittwieser, Joerg H.,Wallner, Silvia,Habibi, Zohreh,Macheroux, Peter,Kroutil, Wolfgang
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supporting information
p. 15051 - 15054
(2016/01/25)
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- Synthesis of bis-Tetrahydroisoquinolines Based on Homoveratrylamine and Several Dibasic Acids. 4. Reaction with Malonic and Succinic Acids
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Bischler-Napieralski cyclization of amides synthesized from homoveratrylamine and malonic and succinic acids produced N-(3,4-dimethoxy-β-phenylethyl)-succinimide, 1,1-bis-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)methane, cleavage products, and several intermediates, the structures of which were confirmed using IR and NMR spectral data and x-ray crystal structure analysis.
- Saidov,Turgunov,Levkovich,Vinogradova
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p. 316 - 319
(2016/01/12)
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- Total Syntheses of Aporphine Alkaloids via Benzyne Chemistry: An Approach to the Formation of Aporphine Cores
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Total syntheses of lysicamine, (±)-nuciferine, (±)-nornuciferine, (±)-zanthoxyphylline iodide, (±)-O-methylisothebaine, and (±)-trimethoxynoraporphine were accomplished by an approach that involves the formation of aporphine cores through reactions betwee
- Rossini, Allan F. C.,Muraca, Ana Carolina A.,Casagrande, Gleison A.,Raminelli, Cristiano
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p. 10033 - 10040
(2015/11/03)
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- Mechanistic and structural analysis of Drosophila melanogaster arylalkylamine N-acetyltransferases
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(Chemical Equation Presented). Arylalkylamine N-acetyltransferase (AANAT) catalyzes the penultimate step in the biosynthesis of melatonin and other N-acetylarylalkylamides from the corresponding arylalkylamine and acetyl-CoA. The N-acetylation of arylalkylamines is a critical step in Drosophila melanogaster for the inactivation of the bioactive amines and the sclerotization of the cuticle. Two AANAT variants (AANATA and AANATB) have been identified in D. melanogaster , in which AANATA differs from AANATB by the truncation of 35 amino acids from the N-terminus. We have expressed and purified both D. melanogaster AANAT variants (AANATA and AANATB) in Escherichia coli and used the purified enzymes to demonstrate that this N-terminal truncation does not affect the activity of the enzyme. Subsequent characterization of the kinetic and chemical mechanism of AANATA identified an ordered sequential mechanism, with acetyl-CoA binding first, followed by tyramine. We used a combination of pH-activity profiling and site-directed mutagenesis to study prospective residues believed to function in AANATA catalysis. These data led to an assignment of Glu-47 as the general base in catalysis with an apparent pKa of 7.0. Using the data generated for the kinetic mechanism, structure-function relationships, pH-rate profiles, and site-directed mutagenesis, we propose a chemical mechanism for AANATA.
- Dempsey, Daniel R.,Jeffries, Kristen A.,Bond, Jason D.,Carpenter, Anne-Marie,Rodriguez-Ospina, Santiago,Breydo, Leonid,Caswell, K. Kenneth,Merkler, David J.
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p. 7777 - 7793
(2015/02/19)
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- Efficient and Practical Syntheses of Enantiomerically Pure (S)-(-)-Norcryptostyline I, (S)-(-)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(-)-Norlaudanosine via a Resolution-Racemization Method
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Four racemic tetrahydroisoquinolines (RS)-(±)-1-4 were prepared from homoveratrylamine via amidation, Bischler-Napieralski reaction and the subsequent reduction. The enantiomerically pure tetrahydroisoquinolines (S)- (-)-norcryptostyline I [(S)-(-)-1], (S)-(-)-norcryptostyline II [(S)-(-)-2], (R)-(+)-salsolidine [(R)-(+)-3] and (S)-(-)-norlaudanosine [(S)-(-)-4] were then obtained in 45%, 40%, 41% and 38% yields, respectively, via resolution of the racemic compounds (RS)-(±)-1-4 with half equivalent of chiral acids. In addition, the enantiomerically enriched compounds (R)-(+)-1, (R)-(+)-2, (S)-(-)-3 and (R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.
- Zhu, Ruiheng,Xu, Zhangli,Ding, Wei,Liu, Shiling,Shi, Xiaoxin,Lu, Xia
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p. 1039 - 1048
(2016/02/18)
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- One-pot α-amidosulfone-mediated variation of the pictet-Spengler tetrahydroisoquinoline synthesis, suitable for amide-type substrates
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The development of Pictet-Spengler reactions from amide substrates is a challenging problem. We report here that the reaction between amide-type compounds (including carbamates, amides, ureas and diketopiperazines), aldehydes and p-toluenesulfinic acid constitutes an efficient method for the preparation of tetrahydroisoquinolines or pyrazino-[2,1-b]isoquinolines. Unlike previously known methods, this one-pot Pictet-Spengler protocol avoids the need for strong Lewis or Br?nsted acid catalysts.
- Arroyo, Francisco J.,López-Alvarado, Pilar,Ganesan,Menéndez, J. Carlos
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supporting information
p. 5720 - 5727
(2014/11/07)
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- Molecular structure effects in the asymmetric transfer hydrogenation of functionalized dihydroisoquinolines on (S,S)-[RuCl(η 6-p-cymene) TsDPEN]
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The asymmetric transfer hydrogenation of five dihydroisoquinolines (DHIQs) was studied by NMR spectroscopy. The DHIQs differed by substitution with methoxy groups, which had a significant effect upon the reaction performance in terms of reaction rate and enantioselectivity. The differences are most probably related to the basicity of DHIQs.
- Vaclavik, Jiri,Pechacek, Jan,Vilhanova, Beata,Sot, Petr,Januscak, Jakub,Matousek, Vaclav,Prech, Jan,Bartova, Simona,Kuzma, Marek,Kacer, Petr
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p. 555 - 562
(2013/07/19)
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- Synthesis, DNA binding and antitumor evaluation of styelsamine and cystodytin analogues
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A series of N-14 sidechain substituted analogues of styelsamine (pyrido[4,3,2-mn]acridine) and cystodytin (pyrido[4,3,2-mn]acridin-4-one) alkaloids have been prepared and evaluated for their DNA binding affinity and antiproliferative activity towards a pa
- Fong, Hugo K.H.,Copp, Brent R.
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p. 274 - 299
(2013/05/21)
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- Synthesis of pyrido[2,1-a]isoquinolin-4-ones and oxazino[2,3-a]isoquinolin- 4-ones: New inhibitors of mitochondrial respiratory chain
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Benzo[a]quinolizine is an important heterocyclic framework that can be found in numerous bioactive compounds. The general scheme for the synthesis of these compounds was based on the preparation of the appropriate dihydroisoquinolines by Bischler-Napieral
- Moreno, Laura,Cabedo, Nuria,Boulangé, Agathe,Párraga, Javier,Galán, Abraham,Leleu, Stéphane,Sanz, María-Jesús,Cortes, Diego,Franck, Xavier
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- A ring-closing metathesis-based approach to the synthesis of (+)-tetrabenazine
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A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-α-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.
- Johannes, Manuel,Altmann, Karl-Heinz
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supporting information; experimental part
p. 3752 - 3755
(2012/09/07)
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- Synthesis and structure-activity relationship of disubstituted benzamides as a novel class of antimalarial agents
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Malaria is a devastating world health problem. Using a compound library screening approach, we identified a novel series of disubstituted benzamide compounds with significant activity against malaria strains 3D7 and K1. These compounds represent a new antimalarial molecular scaffold exemplified by compound 1, which demonstrated EC50 values of 60 and 430 nM against strains 3D7 and K1, respectively. Herein we report our findings on the efficient synthesis, structure-activity relationships, and biological activity of this new class of antimalarial agents.
- Mitachi, Katsuhiko,Salinas, Yandira G.,Connelly, Michele,Jensen, Nicholas,Ling, Taotao,Rivas, Fatima
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supporting information; scheme or table
p. 4536 - 4539
(2012/08/07)
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- The importance of the N-H bond in Ru/TsDPEN complexes for asymmetric transfer hydrogenation of ketones and imines
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Ru(ii) complexes of TsDPEN containing two alkyl groups on the non-tosylated nitrogen atom are poor catalysts for asymmetric transfer hydrogenation of ketones and imines; this observation provides direct evidence for the importance of the N-H interaction i
- Soni, Rina,Cheung, Fung Kei,Clarkson, Guy C.,Martins, Jose E. D.,Graham, Mark A.,Wills, Martin
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supporting information; experimental part
p. 3290 - 3294
(2011/06/21)
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- Iridium-catalyzed asymmetric intramolecular allylic amidation: Enantioselective synthesis of chiral tetrahydroisoquinolines and saturated nitrogen heterocycles
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For the first time iridium catalysis has been used for the synthesis of chiral tetrahydroisoquinolines with excellent yields and high enantioselectivities (see scheme; cod=1,5-cyclooctadiene, DBU=1,8- diazabicyclo[5.4.0]undec-7-ene). These products are important chiral building blocks for the synthesis of biologically active compounds, in particular alkaloids. Copyright
- Teichert, Johannes F.,Fananas-Mastral, Martin,Feringa, Ben L.
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supporting information; experimental part
p. 688 - 691
(2011/04/18)
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- A highly enantioselective access to tetrahydroisoquinoline and β-carboline alkaloids with simple noyori-type catalysts in aqueous media
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Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)-harmicine and (S)-crispine.
- Evanno, Laurent,Ormala, Joel,Pihko, Petri M.
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supporting information; experimental part
p. 12963 - 12967
(2010/06/16)
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- Radical-initiated cyclization as a key step for the synthesis of oxoprotoberberine alkaloids
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The oxoprotoberberine alkaloids 1a-d have been synthesized efficiently from the enamide derivatives 2a-d by a radical-initiated cyclization reaction utilizing n-Bu3SnH/AIBN and CuCl. The enamide derivatives 2a-d were prepared from phenylethylam
- Lee, Chih-Shone,Yu, Tsung-Ching,Luo, Jian-Wen,Cheng, Yen-Yao,Chuang, Che-Ping
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scheme or table
p. 4558 - 4562
(2009/12/03)
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- A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
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A new variation of the Pictet-Spengler reaction for the synthesis of 1-substituted tetrahydroisoquinoline derivatives has been developed. The reaction employs the reduction of N-acylcarbamates by DIBAL-H followed by simultaneous cyclization mediated by BF3·OEt2. The synthetic potential of this method has been illustrated by the synthesis of the tetrahydroisoquinoline alkaloids, (±)-xylopinine, (±)-laudanosine, (±)-8-oxo-O-methylbharatamine, and (±)-isoindoloisoquinolone.
- Kuhakarn, Chutima,Panyachariwat, Nattakan,Ruchirawat, Somsak
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p. 8182 - 8184
(2008/03/14)
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- Synthesis of benzoazocines from substituted tetrahydroisoquinolines and activated alkynes in a tetrahydropyridine ring expansion
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Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Voskressensky, Leonid G.,Listratova, Anna V.,Borisova, Tatiana N.,Alexandrov, Grigoriy G.,Varlamov, Alexey V.
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p. 6106 - 6117
(2008/09/17)
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- QUINOLINE AND ISOQUINOLINE DERIVATIVES AS PHOSPHODIESTERASE 10 INHIBITORS
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The present invention is directed to certain quinoline and isoquinoline compounds that are PDElO inhibitors, pharmaceutical compositions containing such compounds and processes for preparing such compounds. The invention is also directed to methods of treating diseases mediated by PDElO enzyme, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.
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Page/Page column 57
(2010/11/28)
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- Diastereomeric reissert compounds of isoquinoline and 6,7-dimethoxy-3,4- dihydroisoquinoline in stereoselective synthesis
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(Chemical Equation Presented) Chiral acid chlorides were reacted with isoquinoline and 6,7-dimethoxy-3,4-dihydroisoquinoline to form diastereomeric Reissert compounds 8-11 and 18-21, respectively. The best diastereoselectivity (80:20) was achieved in formation of the 9-phenylmenthyl derivative 20. The diastereomers of 2-l-menthoxy-carbonyl-1,2-dihydroisoquinaldonitriles (S)-8/(R)-8), formed in equal amounts, were inseparable. However, the individual diastereomers of 2-cholesteryloxycarbonyl-1,2-dihydroisoquinaldonitriles ((R)-11 and (5)-11) and the 2-l-menthoxycarbonyl-6,7-dimethoxy-1,2,3,4- tetrahydroisoquinaldonitriles ((S)-19/(R)-19)) were each readily purified. (S)-8/(R)-8 (1:1) via the corresponding anions (NaH, -40°C, DMF) with pivaldehyde yielded in 82:18 predominance the S-diastereomer of 1-isoquinolyl tert-butyl carbinyl l-menthyl carbonate ((S)-12), which was obtained in pure form by a single recrystallization; hydrolysis produced 99% pure S-(-)-1-isoquinolyl tert-butyl carbinol [(S)-16]. Reactions of the anions of diastereomeric Reissert compounds, either as mixtures or pure single species, with aromatic aldehydes and alkyl halides proceeded with at best modest selectivity (diastereomeric ratios up to 66:34 and 72:28, respectively). Therefore, it is concluded that the Reissert anions are either planar or rapidly inverting tetrahedral structures.
- Gibson, Harry W.,Berg, Michael A. G.,Dickson, Jennifer Clifton,Lecavalier, Pierre R.,Wang, Hong,Merola, Joseph S.
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p. 5759 - 5770
(2008/02/11)
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- Potential cancer chemopreventive activity of simple isoquinolines, 1-benzylisoquinolines, and protoberberines
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Seventeen simple isoquinolines, 15 1-benzylisoquinolines, and 19 protoberberines were tested for their inhibitory activities against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol- 13-acetate (TPA) in Raji cells. Among the tested alkaloids, the inhibitory activity of all 1-benzylisoquinolines and 11 protoberberines was higher than that of β-carotene. The 1-benzylisoquinolines 19, 21, 22, 29, and 34 and protoberberines 41, 47-49, 51, 52, and 55 showed potent inhibitory effects on EBV-EA induction (96-100% inhibition at 1 × 103 mol ratio/TPA). These alkaloids were more active than the naturally occurring alkaloids, 23, 25, 33, 53, and 54. In addition, fifteen simple isoquinolines, eighteen 1-benzylisoquinolines and eight protoberberines were evaluated with respect to their ability to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals. Nine simple isoquinolines, ten 1-benzylisoquinolines, and four protoberberines were more potent than α-tocopherol, and four 1-benzylisoquinolines, 20 and 28-30, exhibited potent activities (SC50 4.5-5.8 μM). Their activities were higher than the naturally occurring alkaloids, 23, 25, and 33. Therefore, some of the isoquinoline alkaloids indicating the high activity on both assays may be potentially valuable cancer chemopreventive agents. Structure-activity relationships are discussed for both tests.
- Cui, Wenhua,Iwasa, Kinuko,Tokuda, Harukuni,Kashihara, Akiko,Mitani, Yosuke,Hasegawa, Tomoko,Nishiyama, Yumi,Moriyasu, Masataka,Nishino, Hoyoku,Hanaoka, Miyoji,Mukai, Chisato,Takeda, Kazuyoshi
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- Indium metal as a reducing agent in organic synthesis
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The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and α-oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.
- Pitts,Harrison,Moody
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p. 955 - 977
(2007/10/03)
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- Mapping the Melatonin Receptor. 4. Comparison of the Binding Affinities of a Series of Substituted Phenylalkyl Amides
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A series of 2-, 3-, and 4-substituted phenylalkyl amides were prepared as potential melatonin analogs in order to investigate the nature of the binding site of the melatonin receptor in chicken brain.The length of the alkyl chain was systematically varied
- Garratt, Peter J.,Travard, Sylvie,Vonhoff, Stefan,Tsotinis, Andrew,Sugden, David
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p. 1796 - 1805
(2007/10/03)
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- Application of the ortho-Lithiation-Cyclization Strategy to N-Benzyl- and N-Phenethylamine Derivatives
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The ortho-lithiation-cyclization of iodinated N,N-diacylphenethylamines provides a convenient method for the preparation of 2-(2-acetoamidoethyl)acetophenones and 2-(2-benzamidoethyl)benzophenones, which could be easily transformed into dihydroisoquinolines.By contrast, the N-ethylamino, N-acetylamino, and N-trimethylsilylamino moieties studied as ortho-directing groups provide poor assistance to the metalation of N-benzyl- and N-phenyethylamines and the corresponding isoindolone or isoquinolone derivatives are obtained in low yields.
- Lete, Esther,Collado, M. Isabel,Sotomayor, Nuria,Vicente, Teresa,Villa, Maria-Jesus
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p. 1751 - 1758
(2007/10/03)
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- A highly selective protocol for the deprotection of BOC-protected amides and carbamates
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A BOC-protected amide or carbamate undergoes mild and selective deprotection by treatment with catalytic Mg(ClO4)2 in acetonitrile. Simple BOC-protected amines are not affected by these conditions.
- Stafford, Jeffrey A.,Brackeen, Marcus F.,Karanewsky, Donald S.,Valvano, Nicole L.
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p. 7873 - 7876
(2007/10/02)
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- Oxidation Chemistry of the Endogenous Central Nervous System Alkaloid Salsolinol-1-carboxylic Acid
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The oxidation chemistry of salsolinol-1-carboxylic acid (1), an alkaloid endogenous to the central nervous system which is elevated as a result of ethanol consumption, has been studied by electrochemical approaches at pH 7.0 in aqueous solution.The first
- Zhang, Fa,Dryhurst, Glenn
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- A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines
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A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented.Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3.Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields.The method is also highly effective with (2-phenylethyl)amides.
- Larsen, Robert D.,Reamer, Robert A.,Corley, Edward G.,Davis, Paul,Grabowski, Edward J. J.,et al.
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p. 6034 - 6038
(2007/10/02)
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- Selectivity in the propargylation of polyfunctional amines by (propargylium)-Co2(CO)6+ and -(C5H5)2Mo2(CO)4+
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CCH2)Co2(CO)6>BF4 (1) and CCH2)Mo2(C5H5)2(CO)4>BF4 (2) react with primary and secondary amines in CH2Cl2 solution.In the case of primary amines, the products of mono and dialkylation are obtained.The more stable (less reactive) molybdenum co
- Gruselle, M.,Philomin, V.,Chaminant, F.,Jaouen, G.,Nicholas, K. M.
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p. 317 - 326
(2007/10/02)
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- N-Acylcatecholamines and 3,4-Dihydro-6,7-isoquinolinediols from N-Acyl-3,4-dimethoxyphenethylamines
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The N-acetamides 2a and 2e are cleaved with boron tribromide to yield as expected the catechols 3a and 3e whereas, under the same conditions, mixtures of the catechols 3b, 3c, 3f, or 3g and 1-(haloalkyl)dihydroisoquinolines 4
- Niederstein, Yvonne,Peter, Martin G.
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p. 1189 - 1194
(2007/10/02)
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- 2-amino (or hydroxy) phenethyl-1,2,3,4-tetrahydroisoquinolines as analgesics
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Analgesic 1,2,3,4-tetrahydroisoquinolines of the formula (1) STR1 wherein R1 and R2 respectively are hydrogen, hydroxy or alkoxy of 1 to 4 carbon atoms, R3 and R4 respectively are hydrogen or alkyl of 1 to 4 car
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- Dehalogenation of 1-Halogenothienyl-di- and -tetra-hydroisoquinolines by Sodium Methoxide in Dimethyl Sulphoxide
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On treatment with sodium methoxide-dimethyl sulphoxide (NaOMe-DMSO) 1-(5-halogeno-2-thienyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolines suffer loss of halogen and are converted into the related 1-hydroxytetrahydroisoquinolines.The reaction fails with comparable 1-bromophenyl- and 1-(halogeno-3-thienyl)tetrahydroisoquinolines.A similar transformation takes place with (5-halogeno-2-thienyl)phenylmethoxymethanes, leading to the dimethyl acetal of the 5-dehalogenated-2-thienyl phenyl ketone. α-Halogenated-2 and 3-thienyl-3,4-dihydroisoquinolines undergo dehalogenation-aromatisation with NaOMe-DMSO.Mechanisms for these conversions are proposed.
- Barker, John M.,Huddleston, Patrick R.,Clephane, Janette,Wood, Michael L.,Holmes, David
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p. 275 - 282
(2007/10/02)
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- Diazaestrones and analogs. II. Structural modifications of succinimidoethyldihydroisoquinoline, heterosteroid precursor, to establish structure-analgesic activity relationship
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β-1-(succinimidoethyl)-6,7-dimethoxydihydroisoquinoline having exihibited a stronger analgesic activity than the methylester of 2-methoxy-8,13-diazaestrone, its structure has been systematically modified in view of establishing a relation between structur
- Hocquaux,Viel,Brunaud,et al.
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p. 331 - 338
(2007/10/02)
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- Carbon-13 NMR Spectra of Tembamide, Aegeline and Related Amides
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Carbon-13 NMR spectral studies of tembamide (1) and aegeline (2), constituents of Fagara hyemalis and Aegle marmelos respectively, and a series of their structurally related amides (3-13) have been carried out.The assignment of the resonances of two related dimers are also reported.The assignment of the various resonances were made by considering the changes in chemical shifts produced by the change of substituents and also by using 1, 13 and a related compound as model compounds.
- Patra, Amarendra,Mitra, Alok K.,Ghosh, Arundhati,Mukhopadhyay, Prabir K.
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- Etude de l'oxydation de tetrahydroisoquinoleinols-4 dimethoxyles en 6,7 ou 7,8, et sur la reactivite du carbonyle de la tetrahydroisoquinolone-4 dimethoxylee en 6,7
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Preparation des tetrahydroisoquinoleinols-4 mentionnes ci-dessus, et etude de l'oxydation de ceux-ci au moyen de divers reactifs: oxydations chromiques, par les bromamides, le dimethylsulfoxide, la reaction d'Oppenauer.Seule cette derniere a conduit aux t
- Leseche, Bernard,Gilbert, Jacques,Viel, Claude
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p. 143 - 153
(2007/10/02)
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- Intermediates in the preparation of 2,3,4,5-tetrahydro-1H-3-benzazepines
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A process for the preparation of heterocyclic compounds containing one nitrogen atom and novel 2,3,4,5-tetrahydro-1H-3-benzazepines prepared by this process are disclosed. The resulting heterocyclic compounds, including the novel 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives, exhibit analgesic, appetite suppressant, and anti-edema activity.
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