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Related Concept Videos

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles01:11

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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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.
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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 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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Physical Properties of Amines01:26

Physical Properties of Amines

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Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Two New Amides from Physochlainae Radix.

Jin-Yan Tan1, Jian-Li Li1, Pei Li1

  • 1Shanxi Modern Chinese Medicine Engineering Laboratory, Shanxi University of Chinese Medicine, Jinzhong, 030619, P. R. China.

Chemistry & Biodiversity
|July 20, 2023
PubMed
Summary

Two novel amides from Physochlainae Radix exhibit significant anti-inflammatory properties. These compounds effectively inhibit nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 cells.

Keywords:
Physochlaina infundibularisSolanaceaeamidesanti-inflammatory activitieschemical composition

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology

Background:

  • Physochlainae Radix is a potential source of bioactive compounds.
  • Understanding the chemical constituents and biological activities of medicinal plants is crucial.

Purpose of the Study:

  • To isolate and characterize novel chemical compounds from Physochlainae Radix.
  • To evaluate the anti-inflammatory potential of the isolated compounds.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation through comprehensive spectroscopic analyses (NMR, HR-ESI-MS).
  • In vitro anti-inflammatory assay using lipopolysaccharide (LPS)-induced RAW 264.7 cells to measure nitric oxide (NO) production.

Main Results:

  • Two new amides, designated 1 and 2, featuring a unique (2-formyl-5-hydroxymethyl)pyrroyl-butylamine moiety, were successfully isolated.
  • Both compounds demonstrated significant inhibition of NO production.
  • The IC50 values for compounds 1 and 2 were determined to be 17.52±1.68 μM and 20.37±2.42 μM, respectively.

Conclusions:

  • Physochlainae Radix yields novel amides with anti-inflammatory activity.
  • The identified compounds represent promising candidates for further investigation as anti-inflammatory agents.