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Prochirality02:05

Prochirality

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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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Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
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Radical Halogenation: Stereochemistry01:33

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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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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.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
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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 essentially comprises three...
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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Chalcone: A Privileged Structure in Medicinal Chemistry.

Chunlin Zhuang1, Wen Zhang1, Chunquan Sheng1

  • 1School of Pharmacy, Second Military Medical University , 325 Guohe Road, Shanghai 200433, China.

Chemical Reviews
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Summary

Chalcones are versatile privileged structures in medicinal chemistry, offering a simple scaffold for drug discovery. This review highlights their synthesis, biological activities, and mechanisms against various diseases.

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Area of Science:

  • Medicinal Chemistry
  • Organic Chemistry
  • Pharmacology

Background:

  • Privileged structures serve as effective templates in medicinal chemistry for drug discovery.
  • Chalcones represent a common, simple scaffold present in numerous natural products and synthetic compounds.
  • Chalcone derivatives exhibit diverse biological activities with potential clinical applications.

Purpose of the Study:

  • To review recent evidence supporting chalcone as a privileged scaffold in medicinal chemistry.
  • To summarize the isolation of novel chalcone derivatives and advancements in synthetic methodologies.
  • To explore the biological properties, mechanisms of action, and target identification of chalcone compounds.

Main Methods:

  • Literature review of recent studies on chalcone derivatives.
  • Analysis of synthetic approaches for chalcone preparation.
  • Evaluation of biological activities and mechanisms of action reported for chalcones.

Main Results:

  • Chalcones are confirmed as a privileged scaffold with broad biological relevance.
  • Novel chalcone derivatives have been isolated and synthesized.
  • Significant progress in understanding their mechanisms of action and therapeutic potential has been made.

Conclusions:

  • Chalcones are a valuable and versatile scaffold in drug discovery.
  • Further research into chalcone derivatives holds promise for developing new therapeutics.
  • This review provides a comprehensive overview for the chemistry community.