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

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