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Related Concept Videos

Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

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In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
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Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

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The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
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Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

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Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Defenses Against Pathogens and Herbivores

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Plants present a rich source of nutrients for many organisms, making it a target for herbivores and infectious agents. Plants, though lacking a proper immune system, have developed an array of constitutive and inducible defenses to fend off these attacks.
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products

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Ingenane Diterpenoids.

Giovanni Appendino1

  • 1Dipartimento di Scienze del Farmaco, Largo Donegani 2, 28100, Novara, Italy. giovanni.appendino@uniupo.it.

Progress in the Chemistry of Organic Natural Products
|July 6, 2016
PubMed
Summary
This summary is machine-generated.

Ingenol, a Euphorbia diterpenoid, is the only one in its class to reach pharmaceutical development. This review covers ingenol and related compounds, highlighting ongoing research questions in their biogenesis and biological activity.

Keywords:
DiterpenoidsDrug discoveryEuphorbiaIngenolProtein kinase C (PKC)

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Area of Science:

  • Natural Products Chemistry
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Ingenol is a unique Euphorbia diterpenoid, despite challenges like chemical instability and limited availability.
  • Ingenol 3-angelate (ingenol mebutate) was approved in 2012 for actinic keratosis treatment, marking a pharmaceutical milestone.
  • The ingenane class of diterpenoids has been studied since 1968, with significant research up to 2015.

Purpose of the Study:

  • To review the phytochemical, chemical, and biological literature on ingenane diterpenoids from 1968 to 2015.
  • To highlight unresolved issues in the biogenesis and molecular mechanisms of ingenol and related compounds.
  • To discuss the clinical development of ingenol mebutate, focusing on its reverse-pharmacology approach.

Main Methods:

  • Comprehensive literature review of scientific publications.
  • Analysis of phytochemical and chemical characterization data.
  • Examination of biological activity and clinical development studies.

Main Results:

  • Ingenol is the sole Euphorbia diterpenoid with successful pharmaceutical development (ingenol mebutate).
  • Identified common unresolved issues for phorboids (biogenesis, in vivo activity) and specific challenges for ingenol derivatives (stereoisomerism, PKC binding).
  • Discussed ingenol biogenesis in context of macrocyclic diterpenoid formation and ingenol mebutate's clinical path.

Conclusions:

  • Ingenol derivatives present unique chemical and biological complexities requiring further investigation.
  • Understanding ingenol's biogenesis and molecular interactions is crucial for future drug development.
  • The success of ingenol mebutate underscores the therapeutic potential of Euphorbia diterpenoids.