Enantio‐ and Diastereoselective Nucleophilic Addition of N ‐ tert ‐Butylhydrazones to Isoquinolinium Ions through Anion‐Binding Catalysis

SummaryIn a thrombin generation test with continuous registration of thrombin activity in plasma we studied the ability of a variety of thrombin inhibitors of different type and mechanism of action to influence the activity of thrombin after activation of the coagulation system. Depending on the inhibitor, the peak of thrombin activity is delayed and/or reduced.By blocking the active site of generated thrombin inhibitors cause a concentration dependent reduction of the thrombin peak and inhibit feed-back reactions of thrombin resulting in a delay of thrombin generation. Highly potent synthetic active-site directed inhibitors (Ki ≤ 20 nM) reduce the thrombin activity formed in plasma after extrinsic or intrinsic activation with the same efficiency (IC50 0.1 - 0.6 μM) as hirudin. The delay and reduction of thrombin generation by inhibitors of the anion-binding exosite 1 of thrombin is only attributed to an inhibition of feed-back reactions of thrombin. For a 50% reduction of thrombin activity in plasma by this type of inhibitors relatively high concentrations were determined.

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Cambiarenes: Single-Step Synthesis and Anion Binding of a Clip- Shaped Macrocycle with a Redox-Active Core

10.26434/chemrxiv.9795005.v1 ◽

2019 ◽

Author(s):

Riley J. Petersen ◽

Brett J. Rozeboom ◽

Shalisa Oburn ◽

Nolan Blythe ◽

Tanner Rathje ◽

...

Keyword(s):

Electron Density ◽

Single Step ◽

Anion Binding ◽

Host Molecule ◽

Selective Binding ◽

The Core ◽

Redox Active ◽

Active Core ◽

Guest Binding

<div>We report the synthesis of a novel macrocyclic host molecule that forms in a single step from commercially available starting materials. The core of the macrocycle backbone possesses two quinone rings and, thus, is redox-active. Host-guest binding involving the clip-shaped cavity indicates selective binding of pyridine <i>N</i>-oxides based of the electron density of and steric bulk of the anionic oxygen.</div>

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Recent Progress in Chemosensors Using Aldehyde-bearing Fluorophores for the Detection of Specific Analytes and their Bioimaging

Current Medicinal Chemistry ◽

10.2174/0929867325666180117095528 ◽

2019 ◽

Vol 26 (21) ◽

pp. 4003-4028 ◽

Cited By ~ 1

Author(s):

Fangjun Huo ◽

Yaqiong Zhang ◽

Caixia Yin

Keyword(s):

Biomedical Research ◽

Nucleophilic Addition ◽

Recent Progress ◽

Biological Imaging ◽

Tissue Imaging ◽

Fluorescence Probes ◽

Biological Applications ◽

Convenient Procedure ◽

Nucleophilic Mechanism

In recent years, aldehyde-appended fluorescence probes have attracted increasing attention. Fluorescent biological imaging includes many modern applications for cell and tissue imaging in biomedical research. Meanwhile, the nucleophilic mechanism is a very simple and convenient procedure for the preparation of aldehyde-sensing probes. This tutorial review focuses on aldehyde-bearing chemosensors based on nucleophilic addition mechanism with biological applications.

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Formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycine anion

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19890440 ◽

1989 ◽

Vol 54 (2) ◽

pp. 440-445 ◽

Cited By ~ 1

Author(s):

Vladimír Macháček ◽

Alexandr Čegan ◽

Miloš Sedlák ◽

Vojeslav Štěrba

Keyword(s):

Nmr Spectroscopy ◽

Dimethyl Sulfoxide ◽

Equilibrium Constant ◽

Mole Fraction ◽

Nucleophilic Addition ◽

Adduct Formation ◽

First Case ◽

C Nmr

The intramolecular nucleophilic addition of N-methyl-N-(2,4,6-trinitrophenyl)glycine anion in methanol-dimethyl sulfoxide mixtures produces spiro[(3-methyl-5-oxazolidinone)-2,1'-(2',4',6'-trinitrobenzenide)]. The spiro adduct has been identified by means of 1H and 13C NMR spectroscopy. This is the first case when the formation of a Meisenheimer adduct with carboxylate ion is observed. Logarithm of the equilibrium constant of adduct formation increases linearly with the mole fraction of dimethyl sulfoxide in its mixture with methanol.

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Effects of anion binding on the deprotonation reactions of halorhodopsin.

Journal of Biological Chemistry ◽

10.1016/s0021-9258(17)35842-8 ◽

1986 ◽

Vol 261 (6) ◽

pp. 2690-2696 ◽

Cited By ~ 3

Author(s):

B Schobert ◽

J K Lanyi ◽

D Oesterhelt

Keyword(s):

Anion Binding

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Pyrrole-bridged quinones: π-electronic systems that modulate electronic structures by tautomerism and deprotonation

Chemical Communications ◽

10.1039/d1cc02691g ◽

2021 ◽

Author(s):

Shinya Sugiura ◽

Hiromitsu Maeda

Keyword(s):

Infrared Absorption ◽

Electronic Structures ◽

Near Infrared ◽

Ion Pairing ◽

Anion Binding ◽

Electronic Systems

A new series of π-extended quinone derivatives containing a pyrrole bridge exhibited NH/OH-type tautomerization and anion binding along with deprotonation that induced near-infrared absorption and ion-pairing assemblies.

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Anion binding in metal-organic frameworks

Coordination Chemistry Reviews ◽

10.1016/j.ccr.2020.213708 ◽

2021 ◽

pp. 213708

Author(s):

Xin Wu ◽

Lauren K. Macreadie ◽

Philip A. Gale

Keyword(s):

Metal Organic Frameworks ◽

Anion Binding ◽

Metal Organic

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Doubling the Carbonate-Binding Capacity of Nanojars by the Formation of Expanded Nanojars

Molecules ◽

10.3390/molecules26113083 ◽

2021 ◽

Vol 26 (11) ◽

pp. 3083

Author(s):

Wisam A. Al Isawi ◽

Gellert Mezei

Keyword(s):

Co2 Fixation ◽

Binding Capacity ◽

Coordination Complexes ◽

Anion Binding ◽

Ionization Mass ◽

X Ray ◽

Carbonate Ion ◽

Carbonate Ions ◽

Supramolecular Coordination ◽

Hydration Energies

Anion binding and extraction from solutions is currently a dynamic research topic in the field of supramolecular chemistry. A particularly challenging task is the extraction of anions with large hydration energies, such as the carbonate ion. Carbonate-binding complexes are also receiving increased interest due to their relevance to atmospheric CO2 fixation. Nanojars are a class of self-assembled, supramolecular coordination complexes that have been shown to bind highly hydrophilic anions and to extract even the most hydrophilic ones, including carbonate, from water into aliphatic solvents. Here we present an expanded nanojar that is able to bind two carbonate ions, thus doubling the previously reported carbonate-binding capacity of nanojars. The new nanojar is characterized by detailed single-crystal X-ray crystallographic studies in the solid state and electrospray ionization mass spectrometric (including tandem MS/MS) studies in solution.

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