Sunday, May 02, 2010

The Synaptic Leap Experiments on Reaction Attempts

Andrew Lang and I recently reported on the first edition of the Reaction Attempts book and database. Part of the motivation for this was to structure the experiments from the UsefulChem project in both a machine readable format and one that could be browsed as a physical copy. However, we also had in mind the easy integration of other open experiments, especially those labeled as "failed", since these are unlikely to be found by searching conventional reaction archives.

As a demonstration, we have added a series of experiments from The Synaptic Leap, which Michael Wolfle (working as a post-doc with Mat Todd) has posted. All of these reactions involve intermediates in the synthesis of praziquantel, which is a major focus of the Todd group. One group of these reactions involved the attempted synthesis of praziquanamine via a Pictet-Spengler cyclization. Most of these are failed attempts and one successful one.

Adding these experiments to Reaction Attempts was very simple - since the minimum information required is the ChemSpiderIDs (CSIDs) of all the reactants and the product, which a hyperlink to more details. We also added a few more details provided by Michael - such as the solvent, reaction conditions and outcome.

Andy has provided a simple mechanism to pull up all Reaction Attempts for a given reactant with the following url structure:
The number at the end is the CSID for the reactant. Multiple reactants can be pulled from the database by adding more CSIDs separated by commas.

Successful runs in Reaction Attempts are identified with a green check mark:

Again the main idea here is not to exhaustively abstract all pertinent information for an experiment. Rather it is to connect up researchers who are working on similar reactions. Since it requires so little effort to come up with the minimum required information we are hoping to get contributions from other sources.

We will focus next on coming up with more sophisticated ways to retrieve information - such as substructure searching or by reaction type, solvent, etc. We will also periodically publish hard copies of future Reaction Attempts editions.

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