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dc.contributor.advisorWilliams, Douglas
dc.contributor.authorHershenson, Natalie M.
dc.date.accessioned2019-07-08T13:58:15Z
dc.date.available2019-07-08T13:58:15Z
dc.date.issued2018
dc.identifier.urihttp://hdl.handle.net/10920/37196
dc.descriptionxii, 52 p.en_US
dc.description.abstractPrevious studies have shown that natural compound 5-hydroxy-2-(2- phenylethyl)chromone (5-HPEC, 5) acts as a non-nitrogenous antagonist for the serotonin receptor 5-HT2B. Additionally, a 7-hydroxy-2-(2-phenylethyl)chromone (7-HPEC) analog (9a) has shown moderate inhibitory activity against radioligand binding at the serotonin receptor 5-HT2C. This led us to consider that the C-5 hydroxy group may be favorable for 5-HT2B receptor selectivity and that the C-4′ hydroxy group may be favorable for 5-HT2C receptor selectivity. We synthesized 6-hydroxy-2-(2-phenylethyl)chromone (6-HPEC, 10) and its analogs (18a-n) with the goal of gaining more information about the 2-(2- phenylethyl)chromone family. The synthesis of 6-HPEC derivatives was successfully carried out by a three step reaction series. The first step was synthesis of ethyl 3- phenylpropanoate analogs (14a-k) by way of the Wittig reaction followed by a hydrogenation. The second step was the synthesis of the protected acetophenone, 1-(2- hydroxy-5-(methoxymethoxy)phenyl)ethanone (16), and the third step in the synthesis of the 6-HPEC analogs was completed via Claisen condensation resulting in 15-88% yields. We deduced that the reason for a broad spectrum of yields is due to the solvent used for purification, and the allowed time of purification.en_US
dc.format.mimetypeapplication/pdf
dc.language.isoen_USen_US
dc.publisherKalamazoo Collegeen_US
dc.relation.ispartofKalamazoo College Chemistry Senior Individualized Projects Collection
dc.rightsU.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.
dc.titleSynthesis of 6-hydroxy-2-(2-phenylethyl)chromone Derivatives as Potential Serotonin Receptor Ligandsen_US
dc.typeThesisen_US


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    This collection includes Senior Individualized Projects (SIP's) completed in the Chemistry Department. Abstracts are generally available to the public, but PDF files are available only to current Kalamazoo College students, faculty, and staff.

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