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Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

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Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
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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.
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Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
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Proteins are polymers of amino acids linked together by peptide bonds. Proteins and polypeptides are interchangeably used to refer to long chains of amino acids. However, polypeptides have a molecular weight of fewer than 10,000 daltons, while proteins have greater molecular weight.  Polypeptides with less than 20 amino acids are called oligopeptides or simply peptides. Interactions among the constituent amino acid side chains of proteins help them fold into a stable 3-dimensional...
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Binding sites linkages can regulate a protein's function.  For example, enzyme activity is often regulated through a feedback mechanism where the end product of the biochemical process serves as an inhibitor.
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Polyamines and α-Carbonic Anhydrases.

Andrea Scozzafava1, Claudiu T Supuran2, Fabrizio Carta3

  • 1Laboratorio di Chimica Bioinorganica, Università degli Studi di Firenze, Rm. 188, Via della Lastruccia 3, 50019 Sesto Fiorentino, Florence, Italy. andrea.scozzafava@unifi.it.

Molecules (Basel, Switzerland)
|December 17, 2016
PubMed
Summary

Natural products like polyamines are promising inhibitors of carbonic anhydrases (CAs), enzymes crucial for treating diseases like glaucoma and infections. This review explores natural and synthetic polyamines as potential CA modulators.

Keywords:
CA inhibitorspolyaminesspermine

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Area of Science:

  • Biochemistry
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Natural products offer diverse chemical structures for biomedical applications.
  • Carbonic anhydrases (CAs) are key targets for treating glaucoma, tumors, CNS disorders, and infectious diseases.
  • Polyamines and coumarins are emerging as novel CA inhibitors.

Purpose of the Study:

  • To review the current state of knowledge on natural polyamines and their synthetic derivatives.
  • To highlight their potential as inhibitors of human carbonic anhydrases.
  • To explore their therapeutic applications in various diseases.

Main Methods:

  • Literature review of natural product chemistry and enzyme inhibition studies.
  • Analysis of structure-activity relationships for polyamine-based CA inhibitors.
  • Discussion of pharmacological relevance and therapeutic potential.

Main Results:

  • Polyamines, both natural and synthetic, exhibit inhibitory activity against human CAs.
  • These compounds represent atypical chemotypes for CA inhibition.
  • Potential for developing selective CA modulators for various diseases.

Conclusions:

  • Natural products, particularly polyamines, are valuable sources for novel CA inhibitors.
  • Polyamines offer a promising avenue for developing new therapeutics against CA-associated pathologies.
  • Further research into polyamine derivatives could yield selective and effective drugs.