- 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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- Identification of Human Toll-like Receptor 2-Agonistic Activity in Dihydropyridine-Quinolone Carboxamides
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Using a multiplexed, reporter gene-based, high-throughput screen, we identified 9-fluoro-7-hydroxy-3-methyl-5-oxo-N-(pyridin-3-ylmethyl)-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxamide as a TLR2 agonist. Preliminary structure-activity relationship studies on the carboxamide moiety led to the identification of analogues that induce chemokines and cytokines in a TLR2-dependent manner. These results represent new leads for the development of vaccine adjuvants.
- Hu, Ziwei,Banothu, Janardhan,Beesu, Mallesh,Gustafson, Collin J.,Brush, Michael J. H.,Trautman, Kathryn L.,Salyer, Alex C. D.,Pathakumari, Balaji,David, Sunil A.
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supporting information
p. 132 - 136
(2019/01/15)
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- Structure-Activity Relationship Studies with Tetrahydroquinoline Analogs as EPAC Inhibitors
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EPAC proteins are therapeutic targets for the potential treatment of cardiac hypertrophy and cancer metastasis. Several laboratories use a tetrahydroquinoline analog, CE3F4, to dissect the role of EPAC1 in various disease states. Here, we report SAR studies with tetrahydroquinoline analogs that explore various functional groups. The most potent EPAC inhibitor 12a exists as a mixture of inseparable E (major) and Z (minor) rotamers. The rotation about the N-formyl group indeed impacts the activity against EPAC.
- Sonawane, Yogesh A.,Zhu, Yingmin,Garrison, Jered C.,Ezell, Edward L.,Zahid, Muhammad,Cheng, Xiaodong,Natarajan, Amarnath
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supporting information
p. 1183 - 1187
(2017/11/15)
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- Enantiomeric resolution of [(2,2-diphenyl-1,3-dioxolan-4-yl)methyl](2-phenoxyethyl)amine, a potent α1 and 5-HT1A receptor ligand: An in vitro and computational study
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In this paper, the enantiomers of (±)-1, previously studied as α1 and 5-HT1A ligands, were prepared both by resolution of the racemate and asymmetric synthesis. The enantiomeric purity and absolute configuration were determined by me
- Franchini, Silvia,Baraldi, Annamaria,Sorbi, Claudia,Pellati, Federica,Cichero, Elena,Battisti, Umberto M.,Angeli, Piero,Cilia, Antonio,Brasili, Livio
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p. 677 - 690
(2015/04/27)
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- High-Performance Isocyanide Scavengers for Use in Low-Waste Purification of Olefin Metathesis Products
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Three isocyanides containing a tertiary nitrogen atom were investigated for use as small-molecule ruthenium scavenging agents in the workup of olefin metathesis reactions. The proposed compounds are odorless, easy to obtain, and highly effective in removi
- Szczepaniak, Grzegorz,Urbaniak, Katarzyna,Wierzbicka, Celina,Kosiński, Krzysztof,Skowerski, Krzysztof,Grela, Karol
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p. 4139 - 4148
(2015/12/30)
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- Synthesis, enantiomeric separation and docking studies of spiropiperidine analogues as ligands of the nociceptin/orphanin FQ receptor
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A series of triazospirodecanone derivatives were synthesized as potential NOP ligands. 8-(Chroman-4-yl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (4) and its 5-fluoro analogue (18) proved to be active as agonists with EC50 values in the submicromolar range. Single enantiomers of compound 4 were separated and tested as NOP agonists; the eutomer R-(+)-4 showed a pEC 50 of 7.34. Finally docking studies were performed on the NOP receptor to identify the most significant stereospecific interactions.
- Battisti, Umberto M.,Corrado, Sandra,Sorbi, Claudia,Cornia, Andrea,Tait, Annalisa,Malfacini, Davide,Cerlesi, Maria Camilla,Calò, Girolamo,Brasili, Livio
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p. 973 - 983
(2014/07/08)
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- N-tosyl-(S)-prolyl chloride in kinetic resolution of racemic heterocyclic amines
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The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was developed.
- Gruzdev,Vakarov,Levit,Krasnov
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p. 1795 - 1807
(2014/05/06)
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- Diastereoselective acylation of racemic heterocyclic amines with N-tosyl-(S)-prolyl chloride and its structural analogs
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A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.
- Vakarov,Gruzdev,Chulakov,Sadretdinova, L. Sh.,Ezhikova,Kodess,Levit,Krasnov
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p. 838 - 855
(2014/11/08)
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- Diastereoselective acylation of racemic heterocyclic amines with N-tosyl-(s)-prolyl chloride and its structural analogs
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A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.
- Vakarov,Gruzdev,Chulakov,Sadretdinova,Ezhikova,Kodess,Levit,Krasnov
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p. 838 - 855
(2015/09/28)
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- Does an axial propeller shape on a dirhodium(III,III) core affect equatorial ligand chirality?
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The dirhodium(III,III) tetrakis(1-aza-2-cyclooctanoate) framework, which exists solely in a propeller conformation, has been prepared with nonidentical apical aryl ligands. The presence of these nonidentical ligands on the propeller conformation was expec
- Doyle, Michael P.,Shabashov, Dmitry,Zhou, Lei,Zavalij, Peter Y.,Welch, Christopher,Pirzada, Zainab
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p. 3619 - 3627
(2011/09/20)
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- STEROID SPARING AGENTS AND METHODS OF USING SAME
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This invention relates generally to the use of a steroid sparing agent for the preparation of a medicament for the treatment of inflammatory bowel diseases (IBD), asthma, multiple sclerosis (MS), rheumatoid arthritis (RA), graft versus host disease (GVHD), host versus graft disease, and various spondyloarthropathies, comprising administering a steroid sparing immunoglobulin or small molecule composition to a patient in need thereof. The invention also relates generally to combination therapies for the treatment of these conditions.
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Page/Page column 517
(2010/02/14)
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- Preparation of both enantiomers of 1-allyl-1,2,3,4-tetrahydro-β-carboline using allyltin reagents and a chiral auxiliary derived from L-proline
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β-Carboline, which had an acyl group derived from L-proline at the 9-position, reacted with allyltributyltin and 2,2,2-trichloroethyl chloroformate to afford an 1-allyl-1,2-dihydro-β-carboline derivative in a diastereoselective manner. The chiral acyl group at N-9 was readily eliminated by aqueous alkali to give a corresponding carboxylic acid. The formed 1-allyl-1,2-dihydro-β-carboline was transformed via two reduction steps to 1-allyl-1,2,3,4-tetrahydro-β-carboline in high ee. When the allylation was carried out using tetraallyltin instead of allyltributyltin, the stereoselectivity was reversed, and the antipode of the allyl adduct was obtained in high yield and ee in the presence of tin(IV) tetraiodide. Thus, it was found that both enantiomers of 1-allyl-β-carboline were obtained in good enantioselectivities by the use of the same chiral auxiliary.
- Itoh, Takashi,Matsuya, Y?ji,Enomoto, Yasuko,Ohsawa, Akio
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p. 7277 - 7289
(2007/10/03)
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- Synthesis and structure-activity relationships of 7-[3-(1- aminoalkyl)pyrrolidinyl]- and 7-[3-1-aminocycloalkyl)pyrrolidinyl]-quinolone antibacterials
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A series of 7-[3-(1-aminoalkyl and 1-aminocycloalkyl)-1- pyrrolidinyl]quinolones have been prepared and their biological properties evaluated. Among them, 1-(S)-aminoalkyl derivatives exhibited potent antibacterial activities against gram-positive and gram-negative organisms. They had moderate lipophilicity and high aqueous solubility compared to their aminomethyl counterparts; e.g., the 3-(1-aminoethyl)-1-pyrrolidinyl compound (83) showed superior pharmacokinetic properties to its aminomethyl counterpart (6).
- Kimura,Atarashi,Takahashi,Hayakawa
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p. 1442 - 1454
(2007/10/02)
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- Synthesis of N-alpha-(tosylglycylprolyl)-4-amidinophenylalanine amides as thrombin inhibitors
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N alpha-(Tosylprolylglycyl)-4-cyanphenylalanine was synthesized by the reaction of an activated ester and a mixed anhydride, respectively, of Tos-Pro-Gly-OH with 4-cyanophenylalanine. N alpha-(Tosylglycylprolyl)-4-cyanophenylalanine was prepared by reacti
- Voigt,Wagner
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p. 378 - 381
(2007/10/02)
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