Optimized synthesis of Praziquanamine alkyl derivatives via Microwave Reductive Amination.
Faculty Sponsor
Trisha A Russell trisharussell@whitworth.edu
Session Type
Poster Presentation
Research Project Abstract
A method was developed to synthesize alkyl derivatives through a reductive amination of a ketone with an amine utilizing microwave technology. Praziqaunamine and piperidine were the amines used because of their potential pharmaceutical application in a small molecule therapy of the disease Maroteaux-Lamy Syndrome. The molar ratios and duration of reaction were studied to increase the product yield. For acetone the optimized reaction involved a mole ratio of 15:1 prazaquanamine to acetone and a reaction time of 60 minutes. Cyclopentanone was optimized at a mole ratio of 7.5:1 prazaquanamine to cyclopentanone for a reaction time of 60 minutes. For benzaldehyde and piperidine the mole ratio was 1.5:1 of benzaldehyde to piperidine for a duration of 20 minutes. The reactions were optimized to yield a pure sample of all products. The cyclopentyl derivative of praziquanamine was tested in an aryl sulfatase B enzyme assay and reported a 208% +/- 15 % activation of the enzyme at a pH of 6.5.
Session Number
PS3
Location
HUB Multipurpose Room
Abstract Number
PS3-v
Optimized synthesis of Praziquanamine alkyl derivatives via Microwave Reductive Amination.
HUB Multipurpose Room
A method was developed to synthesize alkyl derivatives through a reductive amination of a ketone with an amine utilizing microwave technology. Praziqaunamine and piperidine were the amines used because of their potential pharmaceutical application in a small molecule therapy of the disease Maroteaux-Lamy Syndrome. The molar ratios and duration of reaction were studied to increase the product yield. For acetone the optimized reaction involved a mole ratio of 15:1 prazaquanamine to acetone and a reaction time of 60 minutes. Cyclopentanone was optimized at a mole ratio of 7.5:1 prazaquanamine to cyclopentanone for a reaction time of 60 minutes. For benzaldehyde and piperidine the mole ratio was 1.5:1 of benzaldehyde to piperidine for a duration of 20 minutes. The reactions were optimized to yield a pure sample of all products. The cyclopentyl derivative of praziquanamine was tested in an aryl sulfatase B enzyme assay and reported a 208% +/- 15 % activation of the enzyme at a pH of 6.5.
