Scripps VIVO scripps research logo

  • Index
  • Log in
  • Home
  • People
  • Organizations
  • Research
  • Events
Search form

Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents

Academic Article
uri icon
  • Overview
  • Identity
  • Additional Document Info
  • View All
scroll to property group menus

Overview

related to degree

  • Soenen, Danielle, Ph.D. in Chemistry, Scripps Research 1998 - 2003
  • Boyce, Christopher William, Ph.D. in Organic Chemistry, Medicinal Chemistry, Scripps Research 1994 - 1999

authors

  • Boger, Dale
  • Soenen, Danielle
  • Boyce, Christopher William
  • Hedrick, M. P.
  • Jin, Q.

publication date

  • 2000

journal

  • Journal of Organic Chemistry  Journal

abstract

  • A concise, efficient approach to the total synthesis of ningalin B (1) based on a heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine-->1,2,-diazine-->pyrrole) ideally suited for construction of the densely functionalized pyrrole core found in the natural product is detailed. Examination of the natural product and a number of synthetic intermediates revealed that while lacking inherent cytotoxic activity, many reverse the multidrug-resistant (MDR) phenotype, resensitizing a human colon cancer cell line (HCT116/VM46) to vinblastine and doxorubicin at lower doses than the prototypical agent verapamil.

subject areas

  • Animals
  • Antibiotics, Antineoplastic
  • Antineoplastic Agents
  • Cell Survival
  • Doxorubicin
  • Drug Resistance, Multiple
  • Drug Resistance, Neoplasm
  • Heterocyclic Compounds, 3-Ring
  • Humans
  • Mice
  • Tumor Cells, Cultured
  • Urochordata
scroll to property group menus

Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo9916535

PubMed ID

  • 10789460
scroll to property group menus

Additional Document Info

start page

  • 2479

end page

  • 2483

volume

  • 65

issue

  • 8

©2019 The Scripps Research Institute | Terms of Use | Powered by VIVO

  • About
  • Contact Us
  • Support