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content appropriate for schistosomiosis research

29 Jan

Racemic synthesis of rac-PZQ via the Reissert route

Published by Michael Wolfle

 
The first large scale synthesis of rac-PZQ was developed by the Merck KG and Bayer AG (Merck process).[1,2]  Isoquinoline as a cheap starting material was transformed by the Reissert reaction with cyanide and cyclohexanoyl chloride 2 to the cyano amide 3.
 

 

21 Jan

Sulfur melt data smogasbord

Published by RyanPakula

I've been working on the sulfur melt reaction, trying to optimize the reaction yield of the singly dehydrogenated product (DHP below).  Many studies have been conducted, and here I'll discuss some of what I've found out.
 

NMR Spectroscopy of PZQ

Published by MatTodd on 18 January 2010 - 4:30am

Proton NMR assignment for PZQ has been carried out twice in the literature. Once in a review article: Analytical Profiles of Drug Substances and Excipients, 1998, 25, 463, and once in Arch. Pharm. (Weinheim), 1989, 322, 795-799. Of interest are the large differences in chemical shift between the diastereotopic protons on positions 1 and 6. Need image capture from the pdfs posted below...
 
 
Ryan has posted NMR data in a separate post.
 

Pictet-Spengler route to rac-PZQ

Published by Michael Wolfle on 15 January 2010 - 4:35am

Subject 

Request for Help

 
The synthesis of rac-PZQ via the Pictet-Spengler route was developed by the Korean Shin Poong Pharmaceutical Company and obtains very low production costs of US¢7 per 600 mg tablet of the drug.

A Summary of What is Needed Right Now

Published by MatTodd on 5 January 2010 - 8:42am

Subject 

Request for Help

Project A: Development of a low-cost enantioselective synthesis of PZQ. It's an open project, like everything on TSL.
Meaning?: contributors can change anything they wish on these pages.
If you wish to contribute: please don't leave comments here. Instead, edit the pages below directly or leave comments.

Starting Materials for the Synthesis of rac-PZQ

Published by Michael Wolfle on 5 January 2010 - 8:27am

Subject 

Request for Help

 
For an inexpensive route to rac-PZQ (and potentially the enantioenriched material), the relevant starting materials (below) are required. While prices may be obtained for these from commercial catalogues, we require realistic prices of these materials on a large (ton) scale to assess whether this approach to PZQ is economically viable. The starting materials are:
 

Reissert Approach to rac-PZQ

Published by Michael Wolfle on 5 January 2010 - 8:25am

Subject 

Request for Help

The most obvious, and known, approach to rac-PZQ is using Reissert chemistry.
 
 
This approach has been used in the following publications:
 [1]    Organic Sonochemistry. Synthesis and Use of Reissert compounds under PTC-Ultrasound, J. Ezquerra and J. Alvarez-Builla, J. Heterocyclic Chem. 1988, 25, 917-925.

Racemic Syntheses of PZQ

Published by MatTodd on 5 January 2010 - 5:48am

This page details the various approaches to rac-PZQ

26 Nov

Developing a GC assay

Published by RyanPakula

Recent work has been towards developing a GC assay to quickly monitor the sulfur melt reactions.
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