Design and Synthesis of 7-hydroxy-2-(2-phenylethyl)chromones as Non-Nitrogenous 5-HT2 Receptor Ligands
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Authors
Chang, Rachel S.
Issue Date
2017
Type
Thesis
Language
en_US
Keywords
Alternative Title
Abstract
7-hydroxy-2-(2-phenylethyl)chromones are a class of non-amine, natural products
that have demonstrated a broad range of pharmacological activities such as antiinflammatory
activity. Following previous research conducted on 5-HPEC, 7-HPEC
appears to be an attractive potential ligand candidate for serotonin 2 receptors (5-HT2).
Studies have shown that 7-HPEC displayed similar inhibition towards all three 5-HT2
receptors. However, the transfer of the hydroxyl group on the phenyl ethyl substituent
seemed to have significant effects on the binding of 7-HPEC ligand to the 5-HT2
receptors. In the present study, 7-HPEC analogues were synthesized to later investigate
the structural activity relationships for this class of compounds. All starting material,
including sixteen esters, was synthesized to give high yields, with the exception of one
ester. Twenty-seven 7-HPEC analogues were synthesized via Claisen condensation
followed by the acid-catalyzed cyclization of the condensation to give a wide range of
percent yields. In regards to the yields, there were observed trends that can be explained
by the purification method and solvents used for the trituration. Once purified, twentyfive
of the compounds were sent to a Psychoactive Drug Screening program to be tested
for inhibition on 5-HT2 receptors. Future studies will be to analyze the inhibition data to
provide further insight as to how this natural class of compounds can be used to target
various diseases.
Description
viii, 34 p.
Citation
Publisher
Kalamazoo College
License
U.S. copyright laws protect this material. Commercial use or distribution of this material is not permitted without prior written permission of the copyright holder. All rights reserved.