Synthesis and Biological Evaluation of Novel Indole-Derived Thioureas

Molecules. 2018 Oct 7;23(10):2554. doi: 10.3390/molecules23102554.


A series of 2-(1H-indol-3-yl)ethylthiourea derivatives were prepared by condensation of 2-(1H-indol-3-yl)ethanamine with appropriate aryl/alkylisothiocyanates in anhydrous media. The structures of the newly synthesized compounds were confirmed by spectroscopic analysis and the molecular structures of 8 and 28 were confirmed by X-ray crystallography. All obtained compounds were tested for antimicrobial activity against Gram-positive cocci, Gram-negative rods and for antifungal activity. Microbiological evaluation was carried out over 20 standard strains and 30 hospital strains. Compound 6 showed significant inhibition against Gram-positive cocci and had inhibitory effect on the S. aureus topoisomerase IV decatenation activity and S. aureus DNA gyrase supercoiling activity. Compounds were tested for cytotoxicity and antiviral activity against a large panel of DNA and RNA viruses, including HIV-1 and other several important human pathogens. Interestingly, derivative 8 showed potent activity against HIV-1 wild type and variants bearing clinically relevant mutations. Newly synthesized tryptamine derivatives showed also a wide spectrum activity, proving to be active against positive- and negative-sense RNA viruses.

Keywords: anti-HIV activity; antibacterial activity; antiviral activity; thiourea derivatives of indole; topoisomerase.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Crystallography, X-Ray
  • DNA Gyrase / drug effects
  • DNA Topoisomerase IV / antagonists & inhibitors
  • Humans
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / enzymology
  • Staphylococcus aureus / pathogenicity
  • Thiourea / chemical synthesis*
  • Thiourea / chemistry
  • Thiourea / pharmacology
  • Topoisomerase II Inhibitors / chemical synthesis*
  • Topoisomerase II Inhibitors / chemistry
  • Topoisomerase II Inhibitors / pharmacology


  • Anti-Bacterial Agents
  • Indoles
  • Topoisomerase II Inhibitors
  • DNA Topoisomerase IV
  • DNA Gyrase
  • Thiourea