Pharmacological importance of optically active tetrahydro-β-carbolines and synthetic approaches to create the C1 stereocenter

Molecules. 2014 Jan 27;19(2):1544-67. doi: 10.3390/molecules19021544.

Abstract

1,2,3,4-Tetrahydro-β-carbolines (THβCs) are a pharmacologically important group of compounds belonging to the indole alkaloids. C1-Substituted optically active THβCs have been the target of extensive synthetic efforts due to the presence of the scaffold in numerous natural products and synthetic targets. This review briefly summarizes the methods to obtain the C1 stereocenter and concentrates on evaluating the pharmacological importance of optically active C1-substituted THβCs, including their PDE5-inhibitory, antimalarial, antiviral and antitumor activities.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Antimalarials / chemical synthesis
  • Antimalarials / chemistry
  • Antimalarials / pharmacology
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Biological Products / chemistry*
  • Biological Products / pharmacology
  • Carbolines / chemical synthesis
  • Carbolines / chemistry
  • Carbolines / pharmacology*
  • Drugs, Chinese Herbal / chemical synthesis
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / pharmacology
  • Humans
  • Indole Alkaloids / chemical synthesis
  • Indole Alkaloids / chemistry
  • Molecular Structure
  • Phosphodiesterase 5 Inhibitors / chemistry
  • Phosphodiesterase 5 Inhibitors / pharmacology
  • Stereoisomerism

Substances

  • Antimalarials
  • Antiviral Agents
  • Biological Products
  • Carbolines
  • Drugs, Chinese Herbal
  • Indole Alkaloids
  • Phosphodiesterase 5 Inhibitors
  • antitumor A
  • tryptoline