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Related Concept Videos

Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.6K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.7K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.7K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.2K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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Antimicrobial Proteins01:23

Antimicrobial Proteins

15.2K
Antimicrobial proteins are important components of the immune system. They aid the body in combating pathogens by either killing them directly or hindering their replication processes. Four main types of antimicrobial substances are interferons, the complement system, iron-binding proteins, and antimicrobial proteins.
Interferons
Interferons (IFNs) are proteins produced by lymphocytes, macrophages, and fibroblasts infected with viruses. While IFNs cannot prevent viruses from entering and...
15.2K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.6K
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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Visualization of Bacterial Resistance using Fluorescent Antibiotic Probes
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Small Antimicrobial Agents Based on Acylated Reduced Amide Scaffold.

Peng Teng1, Da Huo2, Alekhya Nimmagadda1

  • 1Department of Chemistry, University of South Florida , 4202 E. Fowler Avenue, Tampa, Florida 33620, United States.

Journal of Medicinal Chemistry
|August 17, 2016
PubMed
Summary

New antibacterial agents combat drug-resistant bacteria by disrupting cell membranes, similar to host-defense peptides. These compounds show promise in treating infections and preventing resistance development.

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Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation
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Area of Science:

  • Medicinal Chemistry
  • Antimicrobial Resistance
  • Molecular Biology

Background:

  • Rising prevalence of multidrug-resistant (MDR) bacteria poses a significant global health threat.
  • Urgent need for novel antibacterial agents with unique mechanisms of action to combat resistance.

Purpose of the Study:

  • To develop and characterize novel small molecular antibacterial agents based on an acylated reduced amide scaffold.
  • To evaluate their efficacy against MDR bacterial strains and their ability to inhibit biofilm formation.
  • To elucidate the mechanism of action and assess their therapeutic potential in a preclinical model.

Main Methods:

  • Synthesis of acylated reduced amide derivatives.
  • Antimicrobial susceptibility testing against Gram-positive and Gram-negative MDR strains.
  • Biofilm inhibition assays.
  • Bacterial membrane integrity assays.
  • Bacterial resistance development studies (e.g., serial passage).
  • In vivo efficacy study in a rat model of MRSA-induced pneumonia.

Main Results:

  • Developed small molecules demonstrated potent activity against a range of MDR bacterial strains.
  • Compounds effectively inhibited bacterial biofilm formation.
  • Mechanistic studies indicated bacterial membrane disruption as the primary mode of action, akin to host-defense peptides.
  • Lead compounds did not induce significant resistance in MRSA after prolonged exposure.
  • In vivo studies showed therapeutic potential in reducing inflammation associated with MRSA pneumonia.

Conclusions:

  • The novel acylated reduced amide scaffold yields potent antibacterial agents effective against MDR bacteria.
  • These compounds exhibit a promising membrane-targeting mechanism that may circumvent existing resistance pathways.
  • The demonstrated efficacy in a preclinical model suggests potential for developing new antibiotics to combat challenging bacterial infections.