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Related Concept Videos

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Basicity of Heterocyclic Aromatic Amines01:25

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 Overview01:07

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.
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...
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.
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.

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Related Experiment Video

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Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
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Structure-Activity Relationships for Some Diamine, Triamine and Schiff Base Derivatives and Their Copper(II)

C A Bolos1, G S Nikolov, L Ekateriniadou

  • 1Laboratory of Inorganic Chemistry Dept. of Chemistry Aristotle University of Thessaloniki 54006 Greece.

Metal-Based Drugs
|May 14, 2008
PubMed
Summary

Copper complexes with polyamines like diethylenetriamine (dien) and dipropylenetriamine (dpta) show potent antibacterial and antiproliferative activities. The Cu(dptaSS)(NO3)2 complex demonstrated significant antibiotic properties against various bacteria.

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Area of Science:

  • Coordination Chemistry
  • Antimicrobial Agents
  • Anticancer Agents

Background:

  • Polyamines and their metal complexes are investigated for biological applications.
  • Schiff bases derived from polyamines can exhibit unique chemical and biological properties.
  • Copper complexes are known for their diverse biological activities.

Purpose of the Study:

  • To synthesize and characterize novel copper(II) complexes with various polyamines and their Schiff bases.
  • To evaluate the antibacterial activity of these compounds against a panel of pathogenic bacteria.
  • To assess the antiproliferative effects of the copper complexes on selected cancer and normal cell lines.

Main Methods:

  • Synthesis and characterization of ethylenediamine, putrescine, diethylenetriamine (dien), dipropylenetriamine (dpta), and spermidine complexes.
  • Preparation of Schiff bases from dien and dpta with 2-furaldehyde, 2-thiophenecarboxaldehyde, and pyrrole-2-carboxaldehyde.
  • Antibacterial screening against Bacillus subtilis, Bacillus cereus, Staphylococcus aureus, Escherichia coli, Proteus vulgaris, and Xanthomonas campestris.
  • Antiproliferative assays using T(47)D, L(929), and BHK(21/c13) cell lines.
  • Electronic structure calculations to determine charge distribution.

Main Results:

  • The copper complex Cu(dptaSS)(NO3)2 exhibited the highest antibacterial activity, acting as an effective antibiotic.
  • Cu(dptaSS)2+ and Cu(dienSS)2+ showed the best antiproliferative results against the tested cell lines.
  • Electronic structure calculations indicated higher negative charges on nitrogen atoms in dptaSS and dienSS.
  • Counter-ions (Br-, NO3-, SO4(2-)) influenced antibacterial selectivity (Gram-positive vs. Gram-negative) but not antiproliferative activity.

Conclusions:

  • Novel copper(II) complexes with polyamines and their Schiff bases possess significant antibacterial and antiproliferative potential.
  • The specific structure of the ligand and the nature of the counter-ion are crucial for modulating biological activity.
  • Cu(dptaSS)(NO3)2 represents a promising lead compound for developing new antibiotics.
  • Further research into these copper complexes could lead to novel therapeutic agents.