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08 Nov

Summary November 8th 2010

Published by MatTodd

We now have two resolutions of PZQ! (or, more correctly, PZQ precursors) The previously-posted resolution (A, see scheme below) involves taking PZQ itself, removing the cyclohexanoyl group to give PZQamine, resolving this amine with a derivative of tartaric acid, then re-introducing the cyclohexanoyl group.

08 Nov

Alternative Approach to the Diamine Precursor

Published by CreativeChemistry

Subject 

Miscellaneous

 We have looked at an alternative process to generate the diamine precursor to PZQ, whose resolution is documented. The process involves reduction of the cyano-imine derived from the published reaction of THIQ with peroxide/tungstate/cyanide. Having been able to reduce 1-cyanoisoquinoline very cleanly using Pd/C we anticipated that it would be possible to do the same here. It would be important, however, to maintain acidic conditions to prevent the retro-addition of the cyanide (well documented for the 1-cyano and 1-(nitromethyl)isoquinolines with a free N-H).
 

Case for characterisation of PZQAmine (or any other resolved intermediate)

Published by ndt228 on 7 November 2010 - 7:38pm

Subject 

Miscellaneous

Now that both racemic and single enantiomer PZQAmine are available, it is possible to determine phase diagrams - either binary, based on MPt, or ternary based upon solubility.  But why do this ?

20 Oct

Praziquantel Update October 20th 2010

Published by MatTodd

A lot has been happening here in the last few weeks, so I ought to summarise:

Aromatic replacements for cyclohexane moiety

Published by MatTodd on 12 September 2010 - 12:47pm


(2-benzoyl-2,3,6,7-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4(11bH)-one)
InChI=1S/C19H18N2O2/c22-18-13-20(19(23)15-7-2-1-3-8-15)12-17-16-9-5-4-6-14(16)10-11-21(17)18/h1-9,17H,10-13H2
SMILES O=C1CN(C(C2=CC=CC=C2)=O)CC3N1CCC4=C3C=CC=C4

PZQ Analogs

Published by MatTodd on 12 September 2010 - 12:45pm

Page dedicated to possible PZQ analogs. Either add below, or create child pages.

Characterization of PZQ-enamide

Published by Ahamed on 25 August 2010 - 5:32am

The PZQ-enamide is shown below. This is an intermediate in the stereoablative route to enantiopure PZQ.

HPLC trace for PZQ-enamide (using ChiralcelOD-H, solvents: Hex:IPA:TEA 60:40:0.1, Flow Rate: 0.7 mL/min) gives retention time: 15.772 mins. Original HPLC trace attached below.
 
(Note comparison HPLC trace for PZQ itself is here.)
 

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