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Synthesis of nitrofuran amide analogues as potential trypanocidal drugs

Synthesis of nitrofuran amide analogues as potential trypanocidal drugs

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An essay for the 2012 Undergraduate Awards (International Programme) Competition by Gavin Stewart. Originally submitted for Chemistry at University of St. Andrews, with lecturer tks1@st-andrews.ac.uk in the category of Mathematical & Physical Sciences
An essay for the 2012 Undergraduate Awards (International Programme) Competition by Gavin Stewart. Originally submitted for Chemistry at University of St. Andrews, with lecturer tks1@st-andrews.ac.uk in the category of Mathematical & Physical Sciences

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Published by: Undergraduate Awards on Aug 31, 2012
Copyright:Attribution Non-commercial

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10/27/2013

 
 Synthesis of nitrofuran amideanalogues as potential trypanocidal drugs
 
 - 2 -
Table of Contents
 _______________________________________________________
 
 I.
 
 Abstract 4 II.
 
 Introduction 5
i.
 
 Human African Trypanosomiasis 5ii.
 
 Aims and Objectives iii.
 
Synthetic Outline 8iv.
 
Structure-Activity Relationship 9v.
 
 Biological Assays 11
 III.
 
 Experimental Methods 12
i.
 
Chemical Synthesis 12ii.
 
 Biological Assays 22
 IV.
 
 Results 24
i.
 
 First Round Compounds 24ii.
 
Second Round Compounds 26 iii.
 
Third Round Compounds 27 
V.
 
 Discussion 29
i.
 
Chemical Synthesis 29ii.
 
 Biological Assays 31iii.
 
Conclusions 34iv.
 
 Future Work 34
VI.
 
 Bibliography 35
 
 - 3 -
 Abbreviations
 ________________________________________________________ 
HAT human African trypanosomiasis
T.b gambiense trypanosoma brucei gambienseT.b. rhodesiense trypanosoma brucei rhodesiense
HIV human immunodeficiency virusAIDS acquired immune deficiency syndromeWHO world health organisationALDH2 aldehyde dehydrogenase 2SAR structure acrivity relationshipED
50
effective dose (50% population)
 
DCM dichloromethane NTR 1 nitroreductase 1 NAD+ nicotinamide adenine dinucleotide NADH nicotinamide adenine dinucleotide hydrideTLC thin layer chromatographyHMI-9 Hirumi's modified Iscove's mediumFCS foetal calf serumDMEM Dulbecco's modified Eagle mediumDMSO dimethyl sulfoxideDCC
 N,N′
-dicyclohexylcarbodiimideDIC
 N,N′
-Diisopropylcarbodiimide

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