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Related Concept Videos

Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of the aromatic...
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Structure of Benzene: Kekulé Model

In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

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In Silico Modeling Method for Computational Aquatic Toxicology of Endocrine Disruptors: A Software-Based Approach Using QSAR Toolbox
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In Silico Modeling Method for Computational Aquatic Toxicology of Endocrine Disruptors: A Software-Based Approach Using QSAR Toolbox

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Skin sensitization structure-activity relationships for phenyl benzoates.

M D Barratt1, D A Basketter, D W Roberts

  • 1Unilever Environmental Safety Laboratory, Sharnbrook, Beds. MK44 1LQ, UK.

Toxicology in Vitro : an International Journal Published in Association with BIBRA
|August 10, 2010
PubMed
Summary
This summary is machine-generated.

Predicting skin sensitization potential relies on chemical structure, not the immune system. Quantitative structure-activity relationships (QSARs) for phenyl benzoate esters show molecular volume and partition coefficient are key, not reactivity.

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Area of Science:

  • Toxicology
  • Computational Chemistry
  • Dermatology

Background:

  • Contact allergens are chemicals that elicit skin sensitization.
  • Predicting allergenic potential is crucial for safety assessment.
  • Quantitative structure-activity relationships (QSARs) offer a predictive approach based on chemical properties.

Purpose of the Study:

  • To develop a QSAR model for predicting the skin sensitization potential of phenyl benzoate esters.
  • To identify key physicochemical parameters influencing contact sensitization within a chemical series.

Main Methods:

  • Synthesis of a diverse range of phenyl benzoate esters.
  • Utilizing computer-based methods to generate a QSAR model.
  • Analyzing parameters including molecular volume, skin penetration, and biological response.

Main Results:

  • The developed QSAR model identified molecular volume and the logarithm of the partition coefficient (ClogP) as significant predictors.
  • Chemical reactivity, while necessary for sensitization, was not a dominant variable in the QSAR model.
  • The study demonstrated the feasibility of deriving a predictive QSAR within a related series of chemicals.

Conclusions:

  • QSAR models can effectively predict skin sensitization potential for related chemicals.
  • Physicochemical properties like molecular size and lipophilicity are critical determinants of allergenic activity.
  • This approach aids in understanding and predicting chemical safety without solely relying on biological testing.