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Amines to Amides: Acylation of Amines

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...

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Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to cholesterol contributes to...

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Physical Properties of Amines

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.

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
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Related Experiment Video

Updated: Jul 17, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

Published on: February 9, 2021

Amides Derived From Sclareolide as Cytotoxic Agents.

Júnio G Silva^1,2, Amanda S de Miranda¹, Tatiane F Borgati^1,3

¹Department of Chemistry, Campus Pampulha, Federal University of Minas Gerais, Belo Horizonte, Minas Gerais, Brazil.

Chemistry & Biodiversity

|July 15, 2026

Summary

Novel drimanamides derived from sclareolide show potent anticancer activity. Compounds 1 and 4 effectively reduced tumor cell viability and induced apoptosis, highlighting their potential as new anticancer drug candidates.

Keywords:

antitumoral cancer drimanamides natural products sclareol

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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

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Last Updated: Jul 17, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay

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Published on: February 9, 2021

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

Area of Science:

Natural product chemistry
Medicinal chemistry
Cancer biology

Background:

Natural products are crucial for anticancer drug discovery.
Sclareolide (SC) serves as a starting point for novel anticancer agents.

Purpose of the Study:

To synthesize and evaluate sclareolide-derived drimanamides for cytotoxicity.
To identify potent anticancer compounds and understand their structure-activity relationships.

Main Methods:

Synthesis of 25 drimanamide derivatives from sclareolide.
Cytotoxicity assessment using the SRB assay against five cancer cell lines (A375, HT29, MCF-7, A2780, HeLa).
Apoptosis and cell cycle analysis using Annexin V/PI and flow cytometry.

Main Results:

Aryl or triazolyl substitutions enhanced cytotoxicity compared to sclareolide.
Compounds 1 and 4 displayed significant cytotoxic profiles (EC50 values as low as 9.2 µM).
Compounds 1 and 4 induced apoptosis in MCF-7 cells and altered cell cycle progression.

Conclusions:

Drimanamides represent a novel class of cytotoxic compounds.
The drimane nucleus is a promising scaffold for anticancer drug design.
Compounds 1 and 4 are potential candidates for further anticancer drug development.