Diethylcarbamazine is a derivative of piperazine. The mechanism of its action is not completely understood. However, it is highly likely that it causes a reduction in muscular activity, and even paralysis in helminthes. It quickly gets rid of the parasites Brugia malayi, Loa loa, and Wuchereria bancrofti, and it is also used for diseases caused by Onchocerca volvulus and Mansonella strptocerca. Synonyms of this drug are hetrazan, notezine, banoside, and others.
Praziquantel: Praziquantel, 2-(cyclcohexylcarbonyl)-1,2,3,6,7,11b-hexahydro-4H-pyrazino [2,1a]isoquinolin-4-one (38.1.15), is a derivative of pyrazinoquinoline that is made in two ways [17-19]. According to one of them, 1-aminomethyl-1,2,3,4-tetrahydroiso-quinoline is alkylated with chloroacetic acid, and then the resulting amine is acylated with cyclohexanecarbonyl chloride to make 1-(N-carboxymethyl-N-cyclohexylcarbonyl-aminomethyl)-1,2,3,4-tetra-hydroisoquinoline (38.1.14), which is heated at 150°C to give the desired praziquantel.
Another way of synthesizing this drug begins with isoquinoline, which is reacted with a mixture of cyclohexanecarbonyl chloride / potassium cyanide to make a dihydro derivative of isoquinoline (38.1.16). This is reduced by hydrogen over Raney nickel to give the reduction-reamidation product—the amide l-(N-cyclohexylcarbonylaminomethyl)-1,2,3,4-tetrahydroisoquinoline (38.1.17). Acylating this with chloracetic acid chloride gives a chlroacetyl derivative (38.1.18), which when heated in the presence of diethylamine results in an intramolecular alkylation, giving the desired product—prazi-quantel.
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