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Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

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The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
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Indirect-Acting Cholinergic Agonists: Mechanism of Action01:18

Indirect-Acting Cholinergic Agonists: Mechanism of Action

2.9K
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,...
2.9K
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

4.1K
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
4.1K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
4.3K
Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship01:29

Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship

1.1K
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...
1.1K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.5K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Phosphonic Acid-Boronic Acid Anhydrides Demonstrate Class A-D β-Lactamase Inhibition.

Elisa Ospanow1, Mirele Barsoum1, Carol A Tanner2

  • 1Dalhousie University, College of Pharmacy and Department of Chemistry, P.O. Box 15,000, Room B03, 5968 College Street, Halifax, Nova Scotia B3H 4R2, Canada.

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Novel boronic acid-phosphonic acid anhydrides show promise as inhibitors of beta-lactamase enzymes. These compounds, particularly compound 12, offer a potential new strategy against antibiotic-resistant bacteria.

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Area of Science:

  • Medicinal Chemistry
  • Drug Discovery
  • Antimicrobial Resistance

Background:

  • Antibiotic resistance is a growing global health threat.
  • Beta-lactamase enzymes are a primary mechanism of resistance to beta-lactam antibiotics.
  • Novel inhibitors are needed to overcome resistance.

Purpose of the Study:

  • To investigate novel boronic acid-phosphonic acid anhydrides as potential beta-lactamase inhibitors.
  • To evaluate their oxidative stability and diol-binding properties.
  • To identify lead compounds for further drug development.

Main Methods:

  • Synthesis of boronic acid-phosphonic acid anhydride compounds.
  • In vitro evaluation of beta-lactamase inhibition for lead compounds.
  • Assessment of oxidative stability and diol-binding.
  • Testing against a panel of clinically relevant beta-lactamases.

Main Results:

  • Two lead compounds, 6 and 12, demonstrated potent inhibition of various beta-lactamases.
  • Compound 12 exhibited broad-spectrum inhibition, including against KPC-2 and GC-1.
  • Effective inhibition was observed at low micromolar concentrations.

Conclusions:

  • The boronic acid-phosphonic acid anhydride scaffold is a promising platform for developing new beta-lactamase inhibitors.
  • Compound 12 shows significant potential for combating antibiotic resistance.
  • This research provides a foundation for rational drug design against resistant infections.