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 ChemistryDrexel University

UsefulChem Project:UsefulChem Project: Open Primary Open Primary Research in Drug Design using Web2.0 Research in Drug Design using Web2.0

toolstools

Docking

Synthesis

Testing

Rajarshi GuhaIndiana U

JC BradleyDrexel U

Phil RosenthalUCSF

(malaria)

Dan ZaharevitzNCI

(tumors)

Tsu-Soo TanNanyang Inst.

Malaria Target: falcipain-2 involved in hemoglobin metabolism

Dana.org

The Ugi Reaction

Outcome of Guha-Bradley-Outcome of Guha-Bradley-Rosenthal collaborationRosenthal 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 Semi-Automated Measurement of solubility via Measurement of solubility via

web service analysis of web service analysis of JCAMP-DX files JCAMP-DX files

(Andy Lang)(Andy Lang)

Raw Data As Images

Splatter?

Some liquid

YouTube for demonstrating experimental YouTube for demonstrating experimental set-upset-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

Khalid Mirza and Marshall Moritz

Top results on a Google search