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The synthesis of anti-malarial
compounds using the Ugi
reaction and
Collaboration using social
software
Jean-Claude Bradley
October 1, 2009
Drexel Chemistry Mini Symposium
Associate Professor of Chemistry
Drexel University
UsefulChem Project: Open Primary
Research in Drug Design using Web2.0
tools
Docking
Synthesis
Testing
Rajarshi Guha
Indiana U
JC Bradley
Drexel U
Phil Rosenthal
UCSF
(malaria)
Dan Zaharevitz
NCI
(tumors)
Tsu-Soo Tan
Nanyang Inst.
Malaria Target: falcipain-2
involved in hemoglobin metabolism
Dana.org
The Ugi Reaction
Outcome of Guha-Bradley-Rosenthal
collaboration
References to papers, blog posts,
lab notebook pages, raw data
Motivation: Faster Science, Better Science
Open Notebook Science Logos
(Andy Lang, Shirley Wu)
Sharing: how much and when
The Ugi reaction: can we predict
precipitation?
Can we predict solubility in organic solvents?
Crowdsourcing Solubility Data
ONS Challenge Judges
ONS Submeta Award Winners
Solubilities collected in a Google
Spreadsheet
Rajarshi Guha’s Live Web Query
using Google Viz API
Data provenance:
From Wikipedia to…
…the lab notebook and raw data
Interactive NMR spectra using JSpecView
and JCAMP-DX
(Andy Lang, Tony Williams)
Open Data JCAMP spectra for education
(Andy Lang, Tony Williams, Robert Lancashire)
Semi-Automated Measurement of
solubility via web service analysis
of JCAMP-DX files
(Andy Lang)
Raw Data As Images
Splatter?
Some liquid
YouTube for demonstrating experimental set-up
The importance of raw data availability
Missed in a prior
publication on solubility
for this compound
Automation and Solubility Measurement
Requests:
DoSol sheet
•Outlier Bot: flags measurements with high standard deviation to mean
ratios
•Google Analytics queries – new solvent/solute searches
•Solubility request form – researcher in Israel requesting pyrene in
acetonitrile solubility for environmental soil contamination study
•Application based models – high priority Ugi reactants
Solvent mixture and temperature:
multidimensional solubility data
Actual Data
(4-nitrobenzaldehyde)
From quadratic regression
of 5D space
Feeds DoSol Sheet the next points to measure to best cover the space
Information spreads quickly through the
blogosphere
The NaH oxidation controversy
15%
NMR
yield
Bradley Lab Research Fall 09 MiniSymposium
Khalid Mirza and Marshall Moritz
Bradley Lab Research Fall 09 MiniSymposium
Top results on a Google search

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Bradley Lab Research Fall 09 MiniSymposium