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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

4.8K
Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Chemical Agents for Microbial Control01:27

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Chemicals play important roles in controlling microbial growth by targeting microbial structures and functions as sanitizers, antiseptics, disinfectants, and sterilants.Alcohols are commonly used sanitizers, effectively disrupting lipid membranes, which compromises cell integrity. They are also used as antiseptics and disinfectants due to their rapid action and versatility.Phenols and their derivatives phenolics , known for denaturing proteins and disrupting cell membranes, are particularly...
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Clinical Significance of Antibiotic Resistance01:25

Clinical Significance of Antibiotic Resistance

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Methicillin-resistant Staphylococcus aureus (MRSA) presents a critical public health threat, arising from its capacity to resist β-lactam antibiotics due to acquisition of the mecA gene within the staphylococcal cassette chromosome mec (SCCmec). This gene encodes penicillin-binding protein 2a (PBP2a), which impairs binding efficacy of methicillin and other β-lactams. MRSA has evolved into distinct clonal lineages impacting humans and animals alike, reinforcing its significance within...
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Halogenated 3-Nitro-2H-Chromenes as Potential Agents Against Multidrug-Resistant Bacteria.

Patrícia I C Godinho1, Paula Pérez-Ramos2, Yaiza Gabasa3,4

  • 1LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.

Antibiotics (Basel, Switzerland)
|March 28, 2025
PubMed
Summary

Researchers synthesized 20 new nitrochromene derivatives to combat antibiotic-resistant bacteria. A tri-halogenated compound, nitrochromene 5s, demonstrated potent activity against Staphylococcus aureus and Staphylococcus epidermidis, showing promise as a novel antibacterial lead.

Keywords:
MDR bacteriaantibacterialchromeneshalogenated drugsnitro derivatives

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Antimicrobial Research

Background:

  • Nosocomial infections caused by antibiotic-resistant strains of Staphylococcus aureus and Staphylococcus epidermidis contribute significantly to global morbidity and mortality.
  • The escalating resistance to conventional antibiotics necessitates the discovery of novel antimicrobial agents.

Purpose of the Study:

  • To synthesize and evaluate the in vitro antibacterial potential of new 2-aryl-3-nitro-2H-chromene derivatives.
  • To identify potent antibacterial agents against multidrug-resistant staphylococcal strains.

Main Methods:

  • Synthesis of 20 novel 2-aryl-3-nitro-2H-chromene derivatives.
  • In vitro evaluation of antibacterial activity using Minimum Inhibitory Concentration (MIC) assays.

Main Results:

  • Mono-halogenated nitrochromenes exhibited moderate anti-staphylococcal activity (MIC: 8-32 μg/mL).
  • Tri-halogenated 3-nitro-2H-chromenes displayed potent activity (MIC: 1-8 μg/mL).
  • Compound 5s (2-(4-bromophenyl)-6-bromo-8-chloro-3-nitro-2H-chromene) showed the highest potency against multidrug-resistant S. aureus and S. epidermidis (MIC: 4 μg/mL and 1-4 μg/mL, respectively).

Conclusions:

  • Nitrochromene 5s demonstrates significant antibacterial activity against resistant staphylococci.
  • Compound 5s possesses a favorable safety profile, positioning it as a promising lead compound for further antibacterial drug development.