- Double-chiral binaphthalene O-N-N tridentate ligand and preparation method thereof
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The invention discloses a bis-chiral binaphthalene O-N-N tridentate ligand and a preparation method thereof. The ligand has the structural formula shown in formula (L). The preparation method comprises the following steps: (1) taking chiral 2 - methyl -2 - methoxy -binaphthalene as a raw material and replacing the reaction with an aromatic ring. As an alternative to the hydroxy protecting group, a brominated derivative (compound IV) is obtained by bromination. (2) Starting from protected chiral proline, a variety of diamine structures are obtained by conversion (Compound B). (3) Compound IV and Compound B are coupled in the presence of a catalyst in the presence of a catalyst to obtain a binaphthalene O-N-N tridentate ligand with bichirality. The ligand preparation method is simple in raw material, and has important significance for asymmetric organic synthesis.
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Paragraph 0054-0056
(2021/09/22)
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- Total Synthesis of Mycenarubin A, Sanguinolentaquinone and Mycenaflavin B and their Cytotoxic Activities
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Here we report the first total synthesis of the fungal alkaloids mycenarubin A, sanguinolentaquinone and mycenaflavin B. The pyrroloquinoline alkaloid mycenarubin A was obtained in 10 steps (21 % total yield, 92 % ee) from the known key precursor 6,7-bis(benzyloxy)indole by an asymmetric alkylation and a biomimetic ring closure as the key steps. The indolo-6,7-quinone sanguinolentaquinone was obtained in eight steps (28 % total yield). Mycenaflavin B was also obtained in eight steps starting from the same key precursor (total yield 15 %) by a biomimetic ring closure and an acid-catalysed decarboxylation reaction as the key steps. The cytotoxic activities of mycenarubin A and mycenaflavin B were evaluated against mouse fibroblasts (L929) and human malignant melanoma cells (RPMI-7951).
- Backenk?hler, Jana,Reck, Bernhard,Plaumann, Markus,Spiteller, Peter
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p. 2806 - 2816
(2018/06/04)
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- NOVEL BETULINIC SUBSTITUTED AMIDE DERIVATIVES AS HIV INHIBITORS
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The present invention relates to novel betulinic substituted amide compounds of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, X, Y, Z1, Z2, Z3 and are Formula (II) as defined herein. The invention novel betulinic substituted amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
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- α-Aminoamides as ligands in Goldberg amidations
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α-Aminoamides are shown to be useful as ligands in Goldberg amidations. A number of α-aminoamides are examined and the importance of substitution on the α-aminoamides is explored. Acetamide is focused on as the nucleophilic coupling partner due to its low cost, stability and convenience as a protecting group. The initial substrate scope for these catalysts is explored and includes electronically activated and deactivated aryl bromides, however o-substituted aryl bromides are problematic.
- Mitra, Aurpon W.,Hansen, Marvin M.,Laurila, Michael E.,Kolis, Stanley P.,Martinelli, Joseph R.
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supporting information
p. 6580 - 6583
(2013/11/19)
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- Easily removable olefin metathesis catalysts
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A small family of olefin metathesis catalysts bearing a polar quaternary ammonium group is described. The presence of this group allows for efficient separation of ruthenium impurities after the reaction. Application of catalysts 9 and 11 leads to organic
- Skowerski, Krzysztof,Wierzbicka, Celina,Szczepaniak, Grzegorz,Gulajski, Lukasz,Bieniek, Michal,Grela, Karol
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supporting information
p. 3264 - 3268
(2013/01/16)
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- An introduction of a pyridine group into the structure of prolyl oligopeptidase inhibitors
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A series of ionizable prolyl oligopeptidase inhibitors were developed through the introduction of a pyridyl group to the P3 position of the prolyl oligopeptidase inhibitor structure. The study was performed on previously developed prolyl oligopeptidase in
- Jarho, Elina M.,Venaelaeinen, Jarkko I.,Juntunen, Juha,Yli-Kokko, A. Leena,Vepsaelaeinen, Jouko,Christiaans, Johannes A.M.,Forsberg, Markus M.,Jaervinen, Tomi,Maennistoe, Pekka T.,Wallen, Erik A.A.
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p. 5590 - 5593
(2007/10/03)
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- Dicarboxylic acid azacycle L-prolyl-pyrrolidine amides as prolyl oligopeptidase inhibitors and three-dimensional quantitative structure-activity relationship of the enzyme-inhibitor interactions
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A series of dicarboxylic acid azacycle L-prolyl-pyrrolidine amides was synthesized, and their inhibitory activity against prolyl oligopeptidase (POP) from porcine brain was tested. Three different azacycles were tested at the position beyond P3 and six different dicarboxylic acids at the P3 position. L-Prolyl-pyrrolidine and L-prolyl-2(S)-cyanopyrrolidine were used at the P2-Pl positions. The IC50 values ranged from 0.39 to 19000 nM. The most potent inhibitor was the 3,3-dimethylglutaric acid azepane L-prolyl-2(S)- cyanopyrrolidine amide. Molecular docking (GOLD) was used to analyze binding interactions between different POP inhibitors of this type and the POP enzyme. The data set consisted of the novel inhibitors, inhibitors published previously by our group, and well-known reference compounds. The alignments were further analyzed using comparative molecular similarity indices analysis. The binding of the inhibitors was consistent at the P1-P3 positions. Beyond the P3 position, two different binding modes were found, one that favors lipophilic structures and one that favors nonhydrophobic structures.
- Jarho, Elina M.,Wallén, Erik A. A.,Christiaans, Johannes A. M.,Forsberg, Markus M.,Ven?l?inen, Jarkko I.,M?nnist?, Pekka T.,Gynther, Jukka,Poso, Antti
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p. 4772 - 4782
(2007/10/03)
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- Design of an organocatalyst for the enantioselective Diels-Alder reaction with α-acyloxyacroleins
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We have realized the first enantioselective organocatalytic Diels-Alder reaction between α-substituted acroleins, such as α-acyloxyacroleins, and not only cyclic but also acyclic dienes. α-Acyloxyacroleins are useful as synthetic equivalents of α-haloacro
- Ishihara, Kazuaki,Nakano, Kazuhiko
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p. 10504 - 10505
(2007/10/03)
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- The chiral diamine mediated asymmetric Baylis-Hillman reaction
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A chiral diamine, easily prepared from proline, is an effective, asymmetric organic catalyst for the Baylis-Hillman reaction of aldehydes and methyl vinyl ketone, affording adducts with enantio-selectivities up to 75%.
- Hayashi, Yujiro,Tamura, Tomohiro,Shoji, Mitsuru
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p. 1106 - 1110
(2007/10/03)
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- Design, Synthesis, and SAR of Potent and Selective Dipeptide-Derived Inhibitors for Dipeptidyl Peptidases
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In this paper we report the systematic search for new, potent, and selective DPP II inhibitors. A study of the structure-activity relationship was conducted starting from aminoacyl pyrrolidides as lead compounds. Rational exploration of the P1
- Senten, Kristel,Van der Veken, Pieter,De Meester, Ingrid,Lambeir, Anne-Marie,Scharpé, Simon,Haemers, Achiel,Augustyns, Koen
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p. 5005 - 5014
(2007/10/03)
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- Asymmetric synthesis of N-substituted (R)-2-[(pyrrolidin-1-yl)methyl]pyrrolidines
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The preparation of (R)-2[(pyrrolidin-1-yl)methyl] pyrrolidine and (R)-1-methyl-2-[(pyrrolidin-1-yl)methyl]pyrrolidine (both in 85% ee) is reported. The key step in the synthesis involves the sparteine-mediated asymmetric functionalization of N-Boc pyrrolidine and subsequent trapping with 1-pyrrolidine-carbonyl chloride.
- Harrison,O'Brien
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p. 1155 - 1160
(2007/10/03)
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- Synthesis of prolyl endopeptidase inhibitors and evaluation of their structure-activity relationships: In vitro inhibition of prolyl endopeptidase from canine brain
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By chemical modification of a known prolyl endopeptidase (PEP) inhibitor (N-[N-(4-phenylbutanoyl)-L-prolyl]pyrrolidine; SUAM-1221), several arylalkanoyl derivatives (V-1-27) were synthesized and tested for in vitro inhibitory activity towards PEP from canine brain. Among them, 4-(2- thienyl)butanoyl derivatives (V-24-27) showed more potent PEP-inhibitory activity than SUAM-1221. The structure-activity relationships of these compounds are discussed.
- Arai,Nishioka,Niwa,Yamanaka,Tanaka,Yoshinaga,Kobayashi,Miura,Ikeda
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p. 1583 - 1588
(2007/10/02)
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- Synthesis and Biological Evaluation of Conformationally Restricted 2-(1-Pyrrolidinyl)-N--N-methylethylenediamines as ? Receptor Ligands. 1. Pyrrolidine, Piperidine, Homopiperidine, and Tetrahydroisoquinoline Classes
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The synthesis and ? receptor affinity of a series of conformationally restricted derivatives of 2-(1-pyrrolidinyl)-N--N-methylethylenediamine (1) is described.The pyrrolidinyl (or N,N-dialkyl), ethylenediamine, N-alkyl, and phenylethyl portions of this ? receptor pharmacophore were restricted by its incorporation into 1,2-cyclohexanediamine-, pyrrolidine-, piperidine-, homopiperidine-, and tetrahydroisoquinoline-containing ligands.The ? receptor binding affinities of these compounds were determined using (+)-pentazocine in guinea pig brain homogenates.The synthesis of all but one class was achieved by acylation and alane reduction of the appropriate diamine precursors whose synthesis is also reported. ? receptor affinities ranged from 1.34 nM for 6,7-dichloro-2-tetrahydroisoquinoline (12) to 455 nM for (1R,2R)-trans-N--N-methyl-2-(1-pyrrolidinyl)cyclohexylamine .In this displacement assay, (+)-pentazocine exhibited a Ki of 3.1 nM while DTG and haloperidol showed Ki values of 27.7 and 3.7 nM, respectively.The conformationally free parent compound 1 exhibited a Ki value of 2.1 nM.Comparison of both the ? receptor affinities and nitrogen atom geometry of the compounds revealed that a gauche relation of the nitrogen atoms of cis-1,2-cyclohexanediamines is not imperative for high affinity as we had previously thought.It is highly likely that nitrogen lone pair orientations and steric factors on the aliphatic portions of these ligands play a major role in the ? receptor binding of this pharmacophore.
- Costa, Brian R. de,Dominguez, Celia,He, Xiao-shu,Williams, Wanda,Radesca, Lilian,Bowen, Wayne
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p. 4334 - 4343
(2007/10/02)
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