The UsefulChem Project:An Application of Open Source Science in Malaria Research

Jean-Claude Bradley PhD, Khalid Mirza, James Giammarco, Dave Strumfels, Lin Cheng

usefulchem.wikispaces.com usefulchem.blogspot.com

Abstract We describe the development of UsefulChem,

an open source science project using blogs and wikis to make the scientific process as transparent as possible.  Blogs are used to

provide RSS information feeds on experimental details, molecules of interest to the projects, and the thinking process behind

the design and evaluation of synthetic strategies. Visitors to the site are able to comment freely on the progress of the

experiments as well as offer solutions to any obstacles that may arise.

Application

This method was applied to a malaria project in which we are synthesizing

diketopiperazine derivatives that have been proposed as candidates for inhibition of enyol reductase, an enzyme required for the malarial

parasite to propagate.

Open science connectivity

More info on open source science here

http://usefulchem.wikispaces.com

UsefulChem Blog

UsefulChem Experiments

UsefulChem Molecules

UsefulChem Writing Partners

UsefulChem Wiki

CMLRSS feed on Bloglines

Automation in UsefulChem

Reasons for Change

The Story of DOPAL

• Unusual Rearrangement of 2-Amino-1-Substituted Phenyl-1-Alkanol to 1-Substituted phenyl-2-AlkanoneJack C. Kim*, Myoung-Do Kong, Man-Yong Yoon, Jin Il Park, Soon-Kyu Choi VOLUME 17 NO 2, 1996, 105-106

Alteration attempts to Synthesize DOPAL

The Successful Synthesis of DOPAL

• Preparation and properties of p-hydroxyphenylacetaldehyde and 3-methoxy-4-hydroxyphenylacetaldehyde Jay H. Robbins, Archives of Biochemistry and Biophysics, Vol 114 Iss 3, June 1966, 576-584

Comparison of NMR data of DOPAL

• Synthesis of a Bichemically Important Aldehyde 3,4-dihydroxy acetaldehydeLi et al, Bioorganic Chemistry, 26, 45-50 1998

3,4-Dihyroxystyrene Dimers, Inducers of Larval Metamorphosis of Ascidians from a Marine Sponge Jaspis spTsukamoto et al, Tetrahedron, Vol 50, No 48, 13583-13592, 1994

Comparison of NMR data of DOPAL

Debugging the Ugi

• Solution Phase Synthesis of Diketopiperazine Libraries Via the Ugi Reaction: Novel Application of Armstrong’s Covertable IsonitrileChristopher Hulme*, Matthew M Morrisette, Francis A Volz, and Christopher J. Burns, Tetrahedron Letters, 39 (1998), 1113-1116

Debugging the Ugi

Progress

Comments on UsefulChem Blogs

Next Steps

• Incorporate our molecules into Emolecules to enable substructure searching

• Custom CMLRSS feeds (e.g. only new commercial sources found)

• Get spectra in JCAMP format• Extend our collaboration with other

chemists (e.g. docking data)• Get our anti-malarials made and tested

References