Design, synthesis, and biofunctional evaluation of novel pentacyclic triterpenes bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety as antiproliferative agents

  • Bioorg Med Chem Lett. 2015 Oct 15;25(20):4500-4. doi: 10.1016/j.bmcl.2015.08.076.
Chun-Hui Zhao  1 ,  Cui-Li Zhang  2 ,  Jin-Jie Shi  1 ,  Xi-Yan Hou  3 ,  Bin Feng  4 ,  Long-Xuan Zhao  5
Affiliations
  • 1. Liaoning Normal University, School of Life Sciences, Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Dalian 116029, China.
  • 2. Dalian Medical University, Department of Biotechnology, Dalian 116044, China.
  • 3. Dalian Nationalities University, College of Life Science, Dalian 116600, China.
  • 4. Dalian Medical University, Department of Biotechnology, Dalian 116044, China. Electronic address: [email protected].
  • 5. Liaoning Normal University, School of Life Sciences, Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Dalian 116029, China; Liaoning Normal University, School of Chemistry and Chemical Engineering, Dalian 116029, China. Electronic address: [email protected].
PMID: 26343825 DOI: 10.1016/j.bmcl.2015.08.076
Abstract

A series of Pentacyclic Triterpenoids derivatives bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety has been synthesized and investigated for their potential antiproliferative activities. Pentacyclic Triterpenoids derivative compounds were synthesized by a four or six step synthetic procedure. The activity studies were evaluated using Cell Counting Kit-8 method, and Western blotting analysis on A549 cells, MCF-7 cells and Hela cells. Compounds methyl 3-O-[4-(1-piperazinyl)-4-oxo-butyryl]olean-12-ene-28-oate (OA-4) and compound 2-O-[4-(1-piperazinyl)-4-oxo-butyryl]-3,23-dihydroxyurs-12-ene-28-oate (AA-5) were found to be promising antiproliferative agents. These compounds show potentiality for further optimization as antitumor drugs.

Keywords
Antiproliferative agent; Apoptosis; Cell cycle; Pentacyclic triterpenoid.