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Related Concept Videos

Structure of Amines01:19

Structure of Amines

The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are illustrated in Figure...
Phase II Reactions: Acetylation Reactions01:24

Phase II Reactions: Acetylation Reactions

Acetylation, a phase II biotransformation reaction, introduces an acetyl group to drugs or their metabolites. Acetyltransferase enzymes facilitate this reaction, which resembles α-amino acid conjugation due to the addition of a functional group to the drug molecule.
The substrates for acetylation are typically drugs or their metabolites with an amino, sulfonamide, or hydrazine functional group. Acetylation can occur at several points in the drug molecule, including primary, secondary, and...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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 amide...
Amines: Introduction01:07

Amines: Introduction

Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

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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Related Experiment Video

Updated: May 13, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
11:01

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

Arylamine N-acetyltransferases: a structural perspective.

Xiaotong Zhou1, Zhiguo Ma, Dong Dong

  • 1Division of Pharmaceutics, College of Pharmacy, Jinan University, Guangzhou, Guangdong, China.

British Journal of Pharmacology
|March 23, 2013
PubMed
Summary
This summary is machine-generated.

Arylamine N-acetyltransferase (NAT) is crucial for metabolizing drugs and carcinogens. Inhibiting NAT shows promise for cancer chemotherapy by targeting its role in cancer cell growth.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Cancer Biology

Background:

  • Arylamine N-acetyltransferase (NAT) enzymes are key in drug and carcinogen metabolism via acetylation.
  • Emerging research implicates NATs in cancer cell proliferation, suggesting potential therapeutic targets.

Purpose of the Study:

  • To explore the role of Arylamine N-acetyltransferase (NAT) in cancer biology.
  • To leverage structural insights of NATs for the development of novel cancer therapeutics.

Main Methods:

  • Analysis of existing three-dimensional (3D) structures of prokaryotic and eukaryotic NATs.
  • Investigating structure-activity relationships for NAT substrates and inhibitors.

Main Results:

  • 3D structures reveal insights into the acetylation mechanism and active site features.
  • Structural data highlights determinants of substrate and inhibitor specificity.
  • Understanding NAT structure-activity relationships facilitates rational drug design.

Conclusions:

  • Structural elucidation of NATs provides a foundation for designing targeted cancer therapies.
  • Inhibiting NAT activity represents a potential strategy for cancer chemotherapy.
  • Targeting NATs could offer a novel approach to cancer treatment.