Efficient Synthesis and Anti-Tubercular Activity of a Series of Spirocycles: An Exercise in Open Science

PLoS One. 2014 Dec 10;9(12):e111782. doi: 10.1371/journal.pone.0111782. eCollection 2014.

Abstract

Tuberculosis afflicts an estimated 2 billion people worldwide and causes 1.3 million deaths annually. Chemotherapeutic solutions rely on drugs developed many years ago, with only one new therapeutic having been approved in the last 40 years. Given the rise of drug-resistant strains, there is an urgent need for the development of a more robust drug development pipeline. GlaxoSmithKline recently placed the structures and activities of 177 novel anti-tubercular leads in the public domain, as well as the results of ongoing optimisation of some of the series. Since many of the compounds arose from screening campaigns, their provenance was unclear and synthetic routes were in many cases not reported. Here we present the efficient synthesis of several novel analogues of one family of the GSK compounds-termed "Spiros"-using an oxa-Pictet-Spengler reaction. The new compounds are attractive from a medicinal chemistry standpoint and some were potent against the virulent strain, suggesting this class is worthy of further study. The research was carried out using open source methodology, providing the community with full access to all raw experimental data in real time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Access to Information
  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Antitubercular Agents / toxicity
  • Cell Line
  • Cell Survival / drug effects
  • Chemistry, Pharmaceutical
  • Chromatography
  • Drug Industry
  • Humans
  • Internet
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Mycobacterium tuberculosis / growth & development
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Antitubercular Agents

Grants and funding

This work was supported by the University of Sydney (KAB, MHT) and the National Health and Medical Research Council Centre of Research Excellence on Tuberculosis Control (APP1043225)(JAT). The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.