The Route Development Towards Dicytoquinazol A Analogs to Investigate Neuroprotective Activity Against Glutamate Excitotoxicity
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Authors
Klemm, Lena
Issue Date
2023-03-01
Type
Thesis
Language
en_US
Keywords
Alternative Title
Abstract
Multiple Sclerosis (MS) is a chronic neurological disease that impacts millions every year and cases continue to grow. A hypothesized mechanism that contributes to MS is glutamate excitotoxicity. A natural product shown to exhibit neuroprotective activity against glutamate excitotoxicity is Dictyoquinazol A. A route was developed to investigate the structural versatility of Dictyoquinazol A. The route consists of three key steps: an amide coupling reaction, a nitro group reduction, and an acid-catalyzed cyclization. The amide coupling reaction proved to be difficult. However, thionyl chloride (SOCl2) revealed to be a successful activating reagent for the synthesis of N-o-(Hydroxymethyl)phenyl5-methoxy-2-nitrobenzamide. However, SOCl2 left sulfur impurities in the nitrobenzamide that prevented the reduction of the nitro group. To avoid the problems presented by SOCl2, oxalyl chloride (CO2Cl2) served as another activating reagent that produced the nitrobenzamide. The successful synthesis can lead to the completion of the nitro group reduction and acid-catalyzed cyclization. The completion of the proposed route enables a model system for the synthesis of Dictyoquinazol A analogs. The synthesis of the analogs will promote the investigation of their structure and neuroprotective activity pertaining to glutamate excitotoxcity.
Description
viii, 20 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.