Molecular Design, Synthesis, and Asymmetric Catalysis of a Hexacoordinated Chiral Phosphate Ion

2018 ◽  
Vol 140 (8) ◽  
pp. 2765-2768 ◽  
Author(s):  
Daisuke Uraguchi ◽  
Hitoshi Sasaki ◽  
Yuto Kimura ◽  
Takaki Ito ◽  
Takashi Ooi
Keyword(s):  
Asymmetric Catalysis ◽  
Molecular Design ◽  
Design Synthesis ◽  
Phosphate Ion

scholarly journals A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis

2020 ◽  
Vol 59 (28) ◽  
pp. 11456-11461 ◽  
Author(s):  
Daisuke Uraguchi ◽  
Fumito Ueoka ◽  
Naoya Tanaka ◽  
Tomohito Kizu ◽  
Wakana Takahashi ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Molecular Design ◽  
Design Synthesis

scholarly journals A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis

2020 ◽  
Author(s):  
Daisuke Uraguchi ◽  
Fumito Ueoka ◽  
Naoya Tanaka ◽  
Tomohito Kizu ◽  
Wakana Takahashi ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Asymmetric Catalysis ◽  
Molecular Design ◽  
Design Strategy ◽  
Vinyl Ethers ◽  
Design Synthesis ◽  
Effective Catalyst ◽  
Structural Robustness ◽  
Selective Chemical ◽  
Selectivity Control

Catalysis by chiral weakly-coordinating anions (WCAs) remains underdeveloped due to the lack of a molecular design strategy for exploiting their characteristics, such as the non-nucleophilic nature. Here, we report the development of a chiral borate ion comprising an <i>O</i>,<i>N</i>,<i>N</i>,<i>O</i>-tetradentate backbone, which ensures hitherto unattainable structural robustness. Upon pairing with a proton, the hydrogen borate acts as an effective catalyst for the asymmetric Prins-type cyclization of vinyl ethers, providing access to structurally and stereochemically defined dihydropyrans. The key to selectivity control is the distinct ability of the borate ion to discriminate the prochiral faces of the acyclic oxonium ion intermediate and dictate the regiochemical outcome. We anticipate that this study paves the way for exploring the untapped potential of WCA catalysis for selective chemical synthesis.<br>

scholarly journals A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis

2020 ◽  
Author(s):  
Daisuke Uraguchi ◽  
Fumito Ueoka ◽  
Naoya Tanaka ◽  
Tomohito Kizu ◽  
Wakana Takahashi ◽  
...  
Keyword(s):  
Chemical Synthesis ◽  
Asymmetric Catalysis ◽  
Molecular Design ◽  
Design Strategy ◽  
Vinyl Ethers ◽  
Design Synthesis ◽  
Effective Catalyst ◽  
Structural Robustness ◽  
Selective Chemical ◽  
Selectivity Control

Catalysis by chiral weakly-coordinating anions (WCAs) remains underdeveloped due to the lack of a molecular design strategy for exploiting their characteristics, such as the non-nucleophilic nature. Here, we report the development of a chiral borate ion comprising an <i>O</i>,<i>N</i>,<i>N</i>,<i>O</i>-tetradentate backbone, which ensures hitherto unattainable structural robustness. Upon pairing with a proton, the hydrogen borate acts as an effective catalyst for the asymmetric Prins-type cyclization of vinyl ethers, providing access to structurally and stereochemically defined dihydropyrans. The key to selectivity control is the distinct ability of the borate ion to discriminate the prochiral faces of the acyclic oxonium ion intermediate and dictate the regiochemical outcome. We anticipate that this study paves the way for exploring the untapped potential of WCA catalysis for selective chemical synthesis.<br>

scholarly journals A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis

2020 ◽  
Vol 132 (28) ◽  
pp. 11553-11558 ◽  
Author(s):  
Daisuke Uraguchi ◽  
Fumito Ueoka ◽  
Naoya Tanaka ◽  
Tomohito Kizu ◽  
Wakana Takahashi ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Molecular Design ◽  
Design Synthesis

Development of Novel Glitazones as Antidiabetic Agents: Molecular Design, Synthesis, Evaluation of Glucose Uptake Activity and SAR Studies

2020 ◽  
Vol 17 (7) ◽  
pp. 840-849
Author(s):  
Mahendra Gowdru Srinivas ◽  
Prabitha Prabhakaran ◽  
Subhankar Probhat Mandal ◽  
Yuvaraj Sivamani ◽  
Pranesh Guddur ◽  
...  
Keyword(s):  
Glucose Uptake ◽  
Molecular Design ◽  
Docking Studies ◽  
Antidiabetic Activity ◽  
Design Synthesis ◽  
In Silico Docking ◽  
Ppar Γ ◽  
Sar Studies ◽  
Structure Activity ◽  
Uptake Activity

Background: Thiazolidinediones and its bioisostere, namely, rhodanines have become ubiquitous class of heterocyclic compounds in drug design and discovery. In the present study, as part of molecular design, a series of novel glitazones that are feasible to synthesize in our laboratory were subjected to docking studies against PPAR-γ receptor for their selection. Methods and Results: As part of the synthesis of selected twelve glitazones, the core moiety, pyridine incorporated rhodanine was synthesized via dithiocarbamate. Later, a series of glitazones were prepared via Knovenageal condensation. In silico docking studies were performed against PPARγ protein (2PRG). The titled compounds were investigated for their cytotoxic activity against 3T3-L1 cells to identify the cytotoxicity window of the glitazones. Further, within the cytotoxicity window, glitazones were screened for glucose uptake activity against L6 cells to assess their possible antidiabetic activity. Conclusion: Based on the glucose uptake results, structure activity relationships are drawn for the title compounds.

scholarly journals Synthesis and Theoretical Investigation Using DFT of 2,3-Diphenylquinoxaline Derivatives for Electronic and Photovoltaic Effects

2021 ◽  
Author(s):  
Dorota Zając ◽  
Dariusz Przybylski ◽  
Jadwiga Sołoducho
Keyword(s):  
Solar Cells ◽  
Acrylic Acid ◽  
Organic Semiconductors ◽  
Organic Solar Cells ◽  
Molecular Design ◽  
Low Cost ◽  
Design Synthesis ◽  
Semiconducting Properties ◽  
Homo Lumo

AbstractDeveloping effective and low‐cost organic semiconductors is an opportunity for the development of organic solar cells (OPV). Herein, we report the molecular design, synthesis and characterization of two molecules with D–A–D–A configuration: 2-cyano-3-(5-(8-(3,4-ethylenodioxythiophen-5-yl)-2,3-diphenylquinoxalin-5-yl)thiophen-2-yl)acrylic acid (6) and 2-cyano-3-(5-(2,3-diphenyl-8-(thiophen-2-yl)quinoxalin-5-yl)thiophen-2-yl)acrylic acid (7). Moreover, we investigated the structural, theoretical and optical properties. The distribution of HOMO/LUMO orbitals and the values of the ionization potential indicate good semiconducting properties of the compounds and that they can be a bipolar material. Also, the optical study show good absorption in visible light (λabs 380–550 nm). We investigate the theoretical optoelectronic properties of obtained compounds as potential materials for solar cells.

Molecular design, synthesis and biological evaluation of 1,4-dihydro-4-oxoquinoline ribonucleosides as TcGAPDH inhibitors with trypanocidal activity

2013 ◽  
Vol 23 (16) ◽  
pp. 4597-4601 ◽  
Author(s):  
Fabyana A. Soares ◽  
Renata Sesti-Costa ◽  
João Santana da Silva ◽  
Maria Cecília B.V. de Souza ◽  
Vitor F. Ferreira ◽  
...  
Keyword(s):  
Molecular Design ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Trypanocidal Activity ◽  
Synthesis And Biological Evaluation

Naphthalimide–thiazoles as novel photonucleases: molecular design, synthesis, and evaluation

2004 ◽  
Vol 45 (6) ◽  
pp. 1247-1251 ◽  
Author(s):  
Yonggang Li ◽  
Yufang Xu ◽  
Xuhong Qian ◽  
Baoyuan Qu
Keyword(s):  
Molecular Design ◽  
Design Synthesis

A novel Golgi mannosidase inhibitor: Molecular design, synthesis, enzyme inhibition, and inhibition of spheroid formation

2020 ◽  
Vol 28 (11) ◽  
pp. 115492
Author(s):  
Ryosuke Koyama ◽  
Yui Kano ◽  
Kaori Kikushima ◽  
Ayaka Mizutani ◽  
Yuta Soeda ◽  
...  
Keyword(s):  
Enzyme Inhibition ◽  
Molecular Design ◽  
Spheroid Formation ◽  
Design Synthesis
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