Synthesis and antitumor activities of sinomenine derivatives on rings A and C

J Asian Nat Prod Res. 2018 Mar;20(3):277-291. doi: 10.1080/10286020.2017.1386659. Epub 2017 Nov 1.

Abstract

A series of new sinomenine derivatives were designed, synthesized, and evaluated in tumor inhibitory activity, such as human triple negative breast cancer cell line (MDA-MB-231), glioma cell line (A172), human lung cancer cell line (A549), human colon cancer cell line (HCT-8). The modifications were carried out on rings A and C of the sinomenine by esterificating on phenolic hydroxyl with good yields. The highlight of this work was that the synthetic procedures were concise and sinomenine derivatives demonstrated promising antitumor activities.

Keywords: Sinomenine; antitumor; derivatives; esterification; modification.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Morphinans / chemical synthesis*
  • Morphinans / chemistry
  • Morphinans / pharmacology*
  • Nuclear Magnetic Resonance, Biomolecular
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Morphinans
  • sinomenine