Synthesis, bioactivity, molecular docking and POM analyses of novel substituted thieno[2,3-b]thiophenes and related congeners

Molecules. 2015 Jan 23;20(2):1824-41. doi: 10.3390/molecules20021824.

Abstract

Several series of novel substituted thienothiophene derivatives were synthesized by reacting the synthone 1 with different reagents. The newly synthesized compounds were characterized by means of different spectroscopic methods such as IR, NMR, mass spectrometry and by elemental analyses. The new compounds displayed significant activity against both Gram-positive and Gram negative bacteria, in addition to fungi. Molecular docking and POM analyses show the crucial role and impact of substituents on bioactivity and indicate the unfavorable structural parameters in actual drug design: more substitution doesn't guaranty more efficiency in bioactivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology
  • Aspergillus fumigatus / drug effects
  • Bacillus subtilis / drug effects
  • Bacterial Proteins / chemistry
  • Candida albicans / drug effects
  • Disk Diffusion Antimicrobial Tests
  • Escherichia coli / drug effects
  • Hydrogen Bonding
  • Molecular Docking Simulation
  • Protein Conformation
  • Pseudomonas aeruginosa / drug effects
  • Streptococcus pneumoniae / drug effects
  • Thiophenes / chemical synthesis*
  • Thiophenes / pharmacology

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Bacterial Proteins
  • Thiophenes