Synthesis and antiproliferative activity of peracetylated 2-amino-1,2-dideoxy-1-nitro-d-glycero-l-manno and d-glycero-d-talo heptitols

Bioorg Chem. 2016 Dec:69:71-76. doi: 10.1016/j.bioorg.2016.09.009. Epub 2016 Sep 23.

Abstract

Michael additions between carbohydrate derived nitroalkenes and several aliphatic and aromatic amines proceeded in a stereoselective way, leading to peracetylated 2-amino-1,2-dideoxy-1-nitro-heptitols. In addition, the antiproliferative activity of some of the new adducts has been studied. The results allowed to identify lead compounds which show GI50 values in the range 1.7-19μM.

Keywords: Amines; Antiproliferative activity; Carbohydrates; Michael reactions; Nitroalkenes; Stereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship
  • Sugar Acids / chemical synthesis
  • Sugar Acids / chemistry
  • Sugar Acids / pharmacology*

Substances

  • Antineoplastic Agents
  • D-glycero-D-talo heptitol
  • Sugar Acids