Molecular design, synthesis and bioactivity of glycosyl hydrazine and hydrazone derivatives: notable effects of the sugar moiety

Bioorg Med Chem Lett. 2011 Dec 1;21(23):7193-6. doi: 10.1016/j.bmcl.2011.09.068. Epub 2011 Sep 22.

Abstract

Assuming that the water solubility of our previous hydrazone derivatives would improve after modification with sugars while keeping or modulating their notable biological activities, we designed and synthesized some glycosyl hydrazine and hydrazone derivatives. Bioassay results indicated that the antitumor activity of our previously prepared hydrazones reduced or disappeared after modification with sugars. On the contrary, some glycosyl derivatives displayed much better antifungal activity against selected fungi. Obviously, a small sugar can change the biological activity of hydrazones significantly.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Carbohydrates* / chemical synthesis
  • Carbohydrates* / chemistry
  • Carbohydrates* / pharmacology
  • Drug Design*
  • Fungi / drug effects*
  • Glycosylation
  • Hydrazines / chemical synthesis
  • Hydrazines / chemistry*
  • Hydrazines / pharmacology
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry*
  • Hydrazones / pharmacology
  • Molecular Structure
  • Solubility
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Antineoplastic Agents
  • Carbohydrates
  • Hydrazines
  • Hydrazones