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Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8'-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents

Academic Article
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Overview

related to degree

  • Totokotsopoulos, Sotirios, Ph.D. in Chemistry, Scripps Research 2009 - 2014
  • Sarlah, David, Ph.D. in Chemistry, Scripps Research 2006 - 2011

authors

  • Nicolaou, K.C.
  • Lu, M.
  • Totokotsopoulos, Sotirios
  • Heretsch, P.
  • Giguere, D.
  • Sun, Y. P.
  • Sarlah, David
  • Nguyen, T. H.
  • Wolf, I. C.
  • Smee, D. F.
  • Day, C. W.
  • Bopp, S.
  • Winzeler, Elizabeth

publication date

  • October 2012

journal

  • Journal of the American Chemical Society  Journal

abstract

  • An improved sulfenylation method for the preparation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines from diketopiperazines has been developed. Employing NaHMDS and related bases and elemental sulfur or bis[bis(trimethylsilyl)amino]trisulfide (23) in THF, the developed method was applied to the synthesis of a series of natural and designed molecules, including epicoccin G (1), 8,8'-epi-ent-rostratin B (2), gliotoxin (3), gliotoxin G (4), emethallicin E (5), and haematocin (6). Biological screening of selected synthesized compounds led to the discovery of a number of nanomolar antipoliovirus agents (i.e., 46, 2,2'-epi-46, and 61) and several low-micromolar anti- Plasmodium falciparum lead compounds (i.e., 46, 2,2'-epi-46, 58, 61, and 1).

subject areas

  • Antimalarials
  • Antiviral Agents
  • Diketopiperazines
  • Dose-Response Relationship, Drug
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Parasitic Sensitivity Tests
  • Plasmodium falciparum
  • Poliovirus
  • Stereoisomerism
  • Structure-Activity Relationship
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Identity

PubMed Central ID

  • PMC3490634

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja308429f

PubMed ID

  • 22978674
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Additional Document Info

start page

  • 17320

end page

  • 17332

volume

  • 134

issue

  • 41

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