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Related Concept Videos

Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

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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...
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Preparation of Amides01:29

Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

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3.9K
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.
3.9K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Related Experiment Video

Updated: Mar 22, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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Optimization of amide-based EP3 receptor antagonists.

Esther C Y Lee1, Kentaro Futatsugi1, Joel T Arcari2

  • 1Worldwide Medicinal Chemistry, Pfizer Worldwide Research & Development, Cambridge, MA 02139, United States.

Bioorganic & Medicinal Chemistry Letters
|April 25, 2016
PubMed
Summary

Developing novel small molecule antagonists for Prostaglandin E receptor subtype 3 (EP3) offers potential treatments for inflammatory and metabolic diseases. This research optimized neutral amide compounds for improved efficiency, moving beyond traditional large, acidic ligands.

Keywords:
EP3 receptorGPCRIndazoleLipEMetabolitesP-gpPGE2

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Area of Science:

  • Medicinal Chemistry
  • Pharmacology

Background:

  • Prostaglandin E receptor subtype 3 (EP3) antagonists are investigated for treating inflammation, cardiovascular, and metabolic diseases.
  • Existing EP3 antagonists are typically large, acidic molecules that mimic prostaglandin E2 (PGE2).

Purpose of the Study:

  • To optimize a series of neutral small molecule amide EP3 antagonists.
  • To improve lipophilic efficiency (LipE/LLE) compared to existing antagonists.

Main Methods:

  • Optimization of a neutral small molecule amide series.
  • Evaluation of lipophilic efficiency (LipE/LLE) metrics.

Main Results:

  • Successful optimization of a neutral small molecule amide series targeting EP3.
  • Achieved improved lipophilic efficiency (LipE/LLE) for the developed compounds.

Conclusions:

  • Neutral small molecule amides represent a promising class of EP3 antagonists.
  • The optimized series offers potential advantages over traditional large, acidic EP3 antagonists.