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Videos de Conceptos Relacionados

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.1K
Drug Metabolism: Phase II Reactions01:14

Drug Metabolism: Phase II Reactions

4.1K
Phase II reactions are essential for the detoxification and elimination of drugs from the body. These reactions involve the conjugation of parent drugs or their phase I metabolites with endogenous molecules, resulting in more hydrophilic drug conjugates. The primary conjugation reactions in this phase are sulfation and glucuronidation. Both sulfation and glucuronidation typically produce biologically inactive metabolites. However, in some cases involving prodrugs, active metabolites may be...
4.1K
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

Phase II Reactions: Sulfation and Conjugation with α-Amino Acids

393
Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
393
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
Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

3.7K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
3.7K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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La ruta modular de dos pasos hacia las sulfonimidamidas

Ze-Xin Zhang1, Charles Bell1, Mingyan Ding1

  • 1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K.

Journal of the American Chemical Society
|June 22, 2022
PubMed
Resumen

Una nueva síntesis en dos pasos permite la creación de sulfondiimidamidas, una clase de moléculas a las que antes era difícil acceder. Este avance ofrece una vía más sencilla y eficiente para el descubrimiento de nuevos compuestos bioactivos que contienen estos importantes grupos funcionales de azufre.

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Área de la Ciencia:

  • Química orgánica
  • Química medicinal
  • Química sintética

Sus antecedentes:

  • Los grupos funcionales del azufre son vitales en las moléculas bioactivas, siendo comunes las sulfonamidas.
  • Los derivados de aza como las sulfoximinas y las sulfonimidamidas están ganando interés.
  • Las sulfonimidamidas, variantes dobles de aza, están en gran parte inexploradas debido a los desafíos sintéticos.

Objetivo del estudio:

  • Desarrollar una vía sintética eficiente y accesible para las sulfonimidamidas.
  • Para superar las limitaciones de los métodos sintéticos multi-paso y caprichosos existentes.
  • Facilitar la aplicación de las sulfondimidas en la química de descubrimiento.

Principales métodos:

  • Se desarrolló una síntesis en dos pasos para las sulfondiimidamidas.
  • El paso clave involucró una aminación mediada por yodo hipervalente.
  • Los materiales de partida incluyen reactivos organometálicos, sulfurodimidas no simétricas y aminas.

Principales resultados:

  • Se han sintetizado más de 40 ejemplares de sulfondiimidamidas.
  • El método produjo derivados de tres fármacos a base de sulfamida.
  • La síntesis demostró la simplicidad operativa, el amplio alcance y la concisión.

Conclusiones:

  • El método desarrollado proporciona una vía práctica y eficiente para las sulfondiimidamidas.
  • Este enfoque mejora significativamente la accesibilidad de las sulfondiimidamidas para el descubrimiento de fármacos.
  • La simplicidad operativa lo hace atractivo para una amplia aplicación en la química de descubrimiento.