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Related Concept Videos

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 para position.
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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, or cyano...
Antiviral Nucleoside Inhibitors01:22

Antiviral Nucleoside Inhibitors

Antiviral Nucleoside InhibitorsAntiviral nucleoside inhibitors are structural analogs of natural nucleosides that interfere with viral DNA or RNA synthesis. These compounds selectively target viral polymerases due to their resemblance to host nucleosides, thereby disrupting viral genome replication.Mechanism of Acyclovir ActionAcyclovir is a guanosine analog with a three-carbon acyclic side chain. It selectively targets herpes simplex virus type 1 (HSV-1), herpes simplex virus type 2 (HSV-2),...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

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...

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Synthesis of dicationic diaryltriazines nucleic acid binding agents.

J Spychala1, Dw Boykin, Wd Wilson

  • 1Department of Chemistry, Georgia State University, Atlanta, GA 30303.

European Journal of Medicinal Chemistry
|May 11, 2011
PubMed
Summary

New triazine compounds were synthesized and tested for DNA/RNA binding and enzyme inhibition. Compounds 6b and 9b strongly bind DNA and inhibit microbial topoisomerase II, showing potential therapeutic applications.

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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

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Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
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Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
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Published on: July 6, 2016

Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Molecular Biology

Background:

  • 1,3,5-triazine derivatives are known for diverse biological activities.
  • Targeting DNA and essential enzymes like topoisomerase II is a key strategy in drug discovery.
  • Developing novel compounds with specific nucleic acid binding properties is crucial for therapeutic advancement.

Purpose of the Study:

  • To synthesize novel 1,3,5-triazine derivatives containing imidazole and tetrahydropyrimidine moieties.
  • To investigate the DNA and RNA binding affinities of these synthesized compounds.
  • To evaluate the inhibitory effects of the compounds on microbial topoisomerase II.

Main Methods:

  • Multi-step organic synthesis was employed to prepare triazine compounds 6a, 6b, 9a, and 9b.
  • Nucleic acid model sequences were used to assess DNA and RNA binding interactions.
  • Enzyme inhibition assays were performed using topoisomerase II isolated from two microbial sources.

Main Results:

  • Compounds 6b and 9b demonstrated strong binding to DNA model sequences.
  • Compounds 6b and 9b exhibited significant inhibition of microbial topoisomerase II.
  • Compounds 6a and 9a bound to both DNA and RNA, while 6b and 9b showed minimal RNA binding.

Conclusions:

  • The synthesized triazine derivatives, particularly 6b and 9b, possess potent DNA-binding and topoisomerase II inhibitory activities.
  • The distinct binding profiles suggest potential for selective targeting of DNA over RNA.
  • These findings highlight the therapeutic potential of these novel compounds as antimicrobial or anticancer agents.