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Related Concept Videos

Physical Properties of Amines01:26

Physical Properties of Amines

3.6K
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.
3.6K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.0K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.1K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.1K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.1K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.1K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.2K
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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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.3K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.3K

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An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity
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An Efficient Method for the Synthesis of Peptoids with Mixed Lysine-type/Arginine-type Monomers and Evaluation of Their Anti-leishmanial Activity

Published on: November 2, 2016

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Heterocyclic Diamines with Leishmanicidal Activity.

Álvaro Martín-Montes1, María Paz Clares2, Rubén Martín-Escolano1,3

  • 1Departamento de Parasitología, Facultad de Ciencias, Universidad de Granada, C/Severo Ochoa s/n, 18071 Granada, Spain.

ACS Infectious Diseases
|November 4, 2021
PubMed
Summary

New compounds targeting leishmaniasis show high efficacy against parasite forms. Three derivatives demonstrate superior activity and lower infectivity rates compared to current treatments, offering potential for chemotherapy.

Keywords:
Fe-SODLeishmaniadiamine derivativesmolecular dynamics

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A Parasite Rescue and Transformation Assay for Antileishmanial Screening Against Intracellular Leishmania donovani Amastigotes in THP1 Human Acute Monocytic Leukemia Cell Line
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Area of Science:

  • Medicinal Chemistry
  • Parasitology
  • Drug Discovery

Background:

  • Leishmaniasis is a neglected tropical disease affecting 12 million people globally.
  • Current treatments are hampered by outdated drugs, and no effective vaccines exist.
  • Developing novel therapeutic agents for leishmaniasis is a critical research objective.

Purpose of the Study:

  • To synthesize and evaluate novel compounds for leishmaniasis treatment.
  • To assess the in vitro and in vivo efficacy of new chemical entities against Leishmania species.
  • To investigate the mechanism of action and selectivity of promising drug candidates.

Main Methods:

  • Synthesis of ten novel compounds linking alkylated ethylenediamine units to pyridine or quinoline heterocycles.
  • In vitro and in vivo testing against promastigote and amastigote forms of *Leishmania infantum*, *Leishmania donovani*, and *Leishmania braziliensis*.
  • Determination of selectivity index, assessment of parasite infectivity rates, and investigation of effects on glucose catabolism and enzyme inhibition.

Main Results:

  • Three compounds (2, 4, and 5) exhibited significantly higher selectivity indices in the amastigote form than glucantime.
  • These compounds reduced parasite infectivity rates more effectively than glucantime at IC25 dose.
  • The novel derivatives demonstrated superior activity against all tested *Leishmania* species compared to glucantime.

Conclusions:

  • The synthesized compounds show promising efficacy as potential leishmaniasis chemotherapeutics.
  • Compounds 2, 4, and 5 are effective against multiple *Leishmania* species and exhibit favorable selectivity.
  • The compounds' mechanism involves altering glucose metabolism and inhibiting iron superoxide dismutase, supporting their potential for leishmaniasis treatment.