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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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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...
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Antimicrobial Effectiveness01:28

Antimicrobial Effectiveness

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The effectiveness of antimicrobial agents depends on various factors influencing their ability to eliminate microbial populations. Larger microbial populations require more time for complete eradication, emphasizing the importance of population size analysis when evaluating antimicrobial efficacy.Microbial resistance to antimicrobial agents varies significantly. Highly resilient microorganisms include endospores, gram-negative bacteria, and non-enveloped viruses, while prions are exceptionally...
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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...
4.2K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

6.5K
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).
6.5K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.0K
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.
3.0K

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Densely Functionalized 2-Methylideneazetidines: Evaluation as Antibacterials.

Giovanni Petrillo1, Cinzia Tavani1, Lara Bianchi1

  • 1Department of Chemistry and Industrial Chemistry, University of Genoa, Via Dodecaneso 31, I-16146 Genoa, Italy.

Molecules (Basel, Switzerland)
|July 2, 2021
PubMed
Summary
This summary is machine-generated.

Novel nitroazetidines show potent antibacterial activity against Gram-positive bacteria like *E. faecalis* and *S. aureus*. Compound 22 is a promising candidate for developing new antibacterials with selective efficacy.

Keywords:
antibioticsdrug resistancegut microbiotavinylogy

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Antimicrobial Drug Discovery

Background:

  • Development of novel antimicrobial agents is crucial due to rising antibiotic resistance.
  • Nitroazetidines represent a class of compounds with potential biological activities.
  • Exploring vinylogous sulfonamides and urethanes for therapeutic applications.

Purpose of the Study:

  • To design and synthesize novel nitroazetidine derivatives.
  • To evaluate the antimicrobial activity of these compounds against various pathogens.
  • To identify potent candidates for further drug development against Gram-positive bacteria.

Main Methods:

  • Synthesis of twenty-two nitroazetidine compounds using a recently developed general procedure.
  • Starting materials included 4-nitropentadienoates derived from a β-nitrothiophenic precursor.
  • Antimicrobial activity testing against Gram-positive bacteria (*E. faecalis*, *S. aureus*), Gram-negative bacteria, and fungi.
  • Cytotoxicity assessment on eukaryotic cells.

Main Results:

  • Most synthesized nitroazetidines exhibited potent antibacterial activity against Gram-positive bacteria.
  • Compounds were inactive against fungi and Gram-negative bacteria.
  • Compound 22 (1-(4-chlorobenzyl)-3-nitro-4-(p-tolyl)azetidine) showed significant potency against *S. aureus* and *E. faecalis* (MIC 1-2 μg/mL).
  • Compound 22 demonstrated selective toxicity, with cytotoxicity on eukaryotic cells occurring at four times higher concentrations than its MIC.

Conclusions:

  • Nitroazetidine derivative 22 is a promising hit compound for developing new antibacterials targeting Gram-positive pathogens.
  • The established synthetic route is concise and utilizes readily available materials, facilitating further structure-activity relationship studies.
  • Further optimization of the toxico-pharmacological profile is warranted for potential clinical applications.