Design, Synthesis and Evaluation of Maleimide- Tryptamine Hybrids as Potential Antibacterial Agents
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Authors
Gough, Mya D.
Issue Date
2020-01-01
Type
Thesis
Language
en_US
Keywords
Alternative Title
Abstract
Antibacterial resistance is developing into a significant health challenge of the 21st century. Presently, there are a finite number of molecular scaffolds displaying antibacterial activity that are FDA approved. This limited structural diversity restricts the number of bactericidal mechanisms available to target. This study used molecular hybridization as a design strategy to develop a novel molecular scaffold with a potentially unique bactericidal mechanism of action. Specifically, maleimides, a class of nitrogen containing heterocycles, were hybridized with tryptamine, the biochemical precursor of tryptophan. Both maleimides and tryptamines have shown antimicrobial activity through mechanisms of action previously not exploited. In this study, 11 maleimides, 4 of which are novel, were synthesized over three steps in yields ranging from 39-93%. Additionally, 22 novel maleimide-tryptamine hybrids were synthesized over a similar three step process in yields from 14-74%. The synthesized compounds were screened against four different strains of Proteus vulgaris via Kirby Bauer Disk Assays. Results indicated that the maleimide-tryptamine hybrids possess greater antibacterial activity than the maleimide controls. Furthermore, several hybrids showed activity against an ampicillin resistant strain of Proteus vulgaris.
Description
viii, 42 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.