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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.6K
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...
2.6K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.1K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.1K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.1K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.1K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.1K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.1K

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Updated: Aug 11, 2025

The Application of Open Searching-based Approaches for the Identification of Acinetobacter baumannii O-linked Glycopeptides
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Aromatic hydrazides: A potential solution for Acinetobacter baumannii infections.

Keith D Green1, Nishad Thamban Chandrika1, Loan Y Vu1

  • 1Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, 789 South Limestone Street, Lexington, KY, 40536-0596, USA.

European Journal of Medicinal Chemistry
|February 5, 2023
PubMed
Summary

Researchers developed new aromatic hydrazides to combat multidrug-resistant bacteria, specifically Acinetobacter baumannii. Many compounds showed potent antibacterial activity with low toxicity, offering a promising new avenue for antibiotic development.

Keywords:
AntibacterialBacteriostatic agentDrug resistanceESKAPE pathogenNarrow spectrum

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Area of Science:

  • Medicinal Chemistry
  • Antimicrobial Drug Discovery
  • Bacteriology

Background:

  • Rising threat of multidrug-resistant bacteria necessitates novel antibiotic development.
  • Acinetobacter baumannii is a high-priority pathogen with significant antibiotic resistance.
  • Existing antibiotics show poor efficacy against resistant bacterial infections.

Purpose of the Study:

  • To synthesize and evaluate novel aromatic hydrazides as potential treatments for Acinetobacter baumannii infections.
  • To identify potent and selective antibacterial agents against multidrug-resistant strains.

Main Methods:

  • Synthesis of a library of 46 aromatic hydrazide compounds.
  • Antimicrobial susceptibility testing using minimum inhibitory concentration (MIC) assays against clinical isolates of Acinetobacter baumannii.
  • Evaluation of compound activity against other bacterial species and assessment of mammalian cytotoxicity.

Main Results:

  • 34 of the synthesized aromatic hydrazides demonstrated low- to sub-micromolar inhibition of Acinetobacter baumannii growth.
  • MIC values ranged from 8 μg/mL to ≤0.125 μg/mL against a broad spectrum of multidrug-resistant clinical isolates.
  • The most potent compound, 3e, exhibited bacteriostatic activity, inhibited biofilm formation, and showed no mammalian cytotoxicity.

Conclusions:

  • The synthesized aromatic hydrazides represent a promising lead series for the development of novel antibiotics targeting Acinetobacter baumannii.
  • High antibacterial potency combined with a lack of mammalian toxicity supports further investigation of these compounds.
  • The selectivity of these compounds against Acinetobacter baumannii is a key advantage for targeted therapeutic development.