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Related Concept Videos

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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
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Chirality02:25

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system...
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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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Chiral Inversion of Pharmaceutical Drugs - Mini Review.

Hassan Y Aboul-Enein1, Valliappan Kannappan2, Selvakumar Kanthiah3

  • 1Pharmaceutical and Medicinal Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Center, Dokki, Cairo 12622, Egypt.

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|January 3, 2023
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Summary

Chiral inversion in nonsteroidal anti-inflammatory drugs (NSAIDs) can change their biological effects. Understanding this process and its influencing factors is crucial for drug safety and efficacy.

Keywords:
Chiral drugsNSAIDs.chiral analysischiral inversionenantiomersstereolabile configuration

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Area of Science:

  • Pharmaceutical Chemistry
  • Medicinal Chemistry
  • Drug Metabolism

Background:

  • 2-Arylpropionic acid nonsteroidal anti-inflammatory drugs (NSAIDs) are a prominent example of chiral inversion in pharmaceuticals.
  • Chiral drugs often exhibit enantiomer-specific pharmacological and toxicological profiles.
  • Chiral inversion can significantly alter a drug's therapeutic and adverse effects.

Approach:

  • Investigating the various factors influencing chiral inversion, including biological, solvent, light, and temperature effects.
  • Examining the energy barriers associated with the stereogenic elements in chiral molecules.
  • Reviewing the methodologies used to determine chiral inversion processes.

Key Points:

  • Chiral inversion is influenced by multiple external and internal factors.
  • The energy barrier of the stereogenic center dictates the rate and extent of inversion.
  • Enantiomer-specific activity means inversion impacts drug efficacy and safety.
  • Understanding chiral inversion is vital for both pharmacological and toxicological assessments.

Conclusions:

  • A comprehensive understanding of chiral inversion mechanisms is essential for developing safer and more effective chiral drugs.
  • Further research into the factors and tools for studying chiral inversion will advance pharmaceutical development.
  • Controlling or predicting chiral inversion is key to optimizing drug performance.