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Synthetic studies on a novel celastrol- fluo-rescent probe for in vivo imaging and novel amination methodologies
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This dissertation was divided into two parts:
Part 1
A novel methodology of aminomethylation of alkenes and alkynes was studied. The methodology developed involved the use of TFA to promote iminium formation from tetramethyldiaminomethane, which in turn reacts with a nucleophilic double bond to deliver an amine. A very well-rounded scope was accomplished with examples that range from aliphatic, cyclic and aromatic alkenes. Functional group tolerance was also pursuit with the method showing a great tolerance towards commonly used groups such as halides and esters. A total number of 25 boc-protected amines were synthesized using alkenes with yields up 82 %.
Part 2
The second part consisted on the development of a fluorescence probe using a fla-vylium ion for in vivo imaging. In order to develop a fluorescent system that could be used in in vivo imaging for detection cancer cells, the prepared flavilyum was coupled with the theraupeutical relevant Celastrol. A new flavilyum ion was synthesized via condensation of a 7-diethylaminophenol with acetophenone possessing an halogenated alkylic linker at the 4’ position. Different pathways were investigated in order to reach and optimize the synthesis of a C4 functionalized flavylium salt that was prepared in three steps. Attempts were performed to couple the prepared flavylium to Celastrol.
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Aminomethylation Amine synthesis Unactivated Alkenes Flavylium coumpounds synthesis of fluorescent compounds celastrol