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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).
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Piperine: bioactivities and structural modifications.

Huan Qu, Min Lv, Hui Xu1

  • 1Research Institute of Pesticidal Design & Synthesis, College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, P.R. China. orgxuhui@nwsuaf.edu.cn.

Mini Reviews in Medicinal Chemistry
|January 2, 2015
PubMed
Summary
This summary is machine-generated.

Piperine, derived from black pepper, and its modified versions show diverse biological activities. This review focuses on structural changes and their impact on piperine

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Area of Science:

  • * Medicinal Chemistry
  • * Natural Product Chemistry
  • * Pharmacology

Background:

  • * Piperine is a key alkaloid from Piper nigrum seeds.
  • * It possesses broad biological properties including antitumor, antioxidant, and anti-inflammatory effects.
  • * Previous reviews primarily focused on biological effects, necessitating a review on structural modifications.

Purpose of the Study:

  • * To review structural modifications of piperine, focusing on the aliphatic chain and amide moiety.
  • * To describe the biological activities of piperine derivatives.
  • * To analyze the structure-activity relationships (SAR) of these modified piperines.

Main Methods:

  • * Literature review of studies on piperine structural modifications.
  • * Analysis of reported biological activities of synthesized piperine derivatives.
  • * Correlation of structural changes with observed biological effects.

Main Results:

  • * Structural modifications on piperine's aliphatic chain and amide moiety yield derivatives with diverse biological activities.
  • * Specific modifications can enhance or alter activities like antitumor, antioxidant, and anti-inflammatory properties.
  • * Structure-activity relationship studies provide insights into optimizing piperine derivatives for therapeutic potential.

Conclusions:

  • * Structural modification is a viable strategy to develop novel piperine derivatives with tailored biological activities.
  • * Understanding the SAR of piperine derivatives is crucial for drug discovery and development.
  • * Further research into piperine analogs holds promise for new therapeutic agents.