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Basicity of Heterocyclic Aromatic Amines

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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.

Amines to Sulfonamides: The Hinsberg Test

Amines to Sulfonamides: The Hinsberg Test

The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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.

Acid Halides to Amides: Aminolysis

Acid Halides to Amides: Aminolysis

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.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...

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Updated: Jun 5, 2026

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

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

Published on: November 23, 2016

New furin inhibitors based on weakly basic amidinohydrazones.

Frank Sielaff¹, Manuel E Than, Dorian Bevec

¹Department of Pharmaceutical Chemistry, Philipps University Marburg, Marbacher Weg 6, D-35032 Marburg, Germany.

Bioorganic & Medicinal Chemistry Letters

|December 21, 2010

Summary

Novel amidinohydrazone compounds were synthesized as potent furin inhibitors. The most effective compounds, 17 and 21, show strong inhibition, with compound 21 featuring modified basic groups for potential therapeutic applications.

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Area of Science:

Medicinal Chemistry
Biochemistry
Drug Discovery

Background:

Furin is a key proprotein convertase involved in various biological processes, including viral entry and disease pathogenesis.
Inhibiting furin activity presents a therapeutic strategy for diseases driven by its proteolytic function.

Purpose of the Study:

To design and synthesize a novel series of amidinohydrazone-derived compounds as potential furin inhibitors.
To evaluate the inhibitory potency of these novel compounds against furin.

Main Methods:

Chemical synthesis of amidinohydrazone derivatives.
Biochemical assays to determine inhibition constants (K(i)) against furin.

Main Results:

A series of amidinohydrazone-derived furin inhibitors were successfully prepared.
Compounds 17 and 21 demonstrated potent furin inhibition with K(i) values of 0.46 μM and 0.59 μM, respectively.
Compound 21, unlike inhibitor 17, lacks a guanidino residue and possesses only weakly basic amidinohydrazone groups.

Conclusions:

Novel amidinohydrazone derivatives are effective inhibitors of furin.
The structural modifications in compound 21, specifically the weakly basic amidinohydrazone groups, offer a distinct chemical profile compared to guanidino-containing inhibitors.
These findings support the potential of amidinohydrazone scaffolds for developing targeted furin inhibitors.