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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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ortho–para-Directing Deactivators: Halogens01:24

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Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship01:29

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Indirect-acting cholinergic agonists are agents that interact with the acetylcholinesterase enzyme in the synaptic cleft, preventing the breakdown of acetylcholine into choline and acetate. Consequently, the concentration of acetylcholine in the synaptic cleft increases. These agonists can be classified into reversible and irreversible inhibitors based on their duration of action.
Reversible inhibitors display short to medium durations of action. Short-acting agents include simple alcohols with...
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Indirect-Acting Cholinergic Agonists: Mechanism of Action01:18

Indirect-Acting Cholinergic Agonists: Mechanism of Action

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Indirect-acting cholinergic agonists work by interacting with an enzyme called acetylcholinesterase (AChE) in the synaptic cleft. They can be reversible or irreversible inhibitors and have different effects on the enzyme.
Reversible inhibitors like edrophonium bind to a specific part of the enzyme called the anionic catalytic site. They form noncovalent bonds, which means they are not strongly attached to the enzyme. This creates a temporary and less stable enzyme–inhibitor complex,...
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Development of Inhibitors of Protein-protein Interactions through REPLACE: Application to the Design and Development Non-ATP Competitive CDK Inhibitors
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Aromatic Diboronic Acids as Effective KPC/AmpC Inhibitors.

Joanna Krajewska1, Piotr Chyży2, Krzysztof Durka3

  • 1Department of Pharmaceutical Microbiology and Bioanalysis, Medical University of Warsaw, 02-097 Warsaw, Poland.

Molecules (Basel, Switzerland)
|November 14, 2023
PubMed
Summary

Ortho-phenylenediboronic acid 3a shows strong synergy with carbapenems against KPC carbapenemases, reducing their minimum inhibitory concentrations. This compound is a promising, non-toxic scaffold for developing new inhibitors against resistant bacteria.

Keywords:
KPC/AmpC β-lactamase inhibitorsantibacterial activityarylboronic acidsmolecular dockingtime-dependent QM/MM

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Biochemistry

Background:

  • Beta-lactamase enzymes, particularly KPC-type carbapenemases, confer resistance to essential antibiotics.
  • Novel inhibitors are urgently needed to combat rising antimicrobial resistance.

Purpose of the Study:

  • To investigate phenylenediboronic acids and related compounds as potential inhibitors of beta-lactamases.
  • To identify specific compounds and elucidate their mechanism of action against KPC carbapenemases.

Main Methods:

  • Synthesis and screening of over 30 boron-containing compounds.
  • Checkerboard assays to evaluate synergistic effects with carbapenems.
  • Enzyme inhibition assays (nitrocefin hydrolysis) and whole-cell assays.
  • Quantum mechanics/molecular mechanics (QM/MM) modeling.

Main Results:

  • Ortho-phenylenediboronic acid 3a demonstrated the highest activity against KPC carbapenemases, significantly reducing carbapenem MICs.
  • Synergistic effects were observed between carbapenems and compound 3a (FIC indices 0.1-0.32).
  • Compound 3a was confirmed to target the KPC enzyme, with QM/MM modeling showing covalent binding to Ser70.

Conclusions:

  • Ortho-phenylenediboronic acids exhibit potent synergistic activity with carbapenems against KPC-producing bacteria.
  • The investigated compounds, particularly 3a, are non-toxic to human fibroblasts and represent promising scaffolds for novel KPC/AmpC inhibitor development.