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Violacein is a purple bacterial pigment produced by several strains of Gram-negative bacteria as a product of microbial secondary metabolism. Its antimicrobial property has shown to make it a potential therapeutic agent. The violacein core/backbone is comprised of indole, pyrrolidone, and isatin. An environmentally friendly, facile synthesis of violacein has been previously developed by our research group. This versatile methodology to synthesize violacein has enabled the convenient preparation of a variety of analogs. To study the Structure Activity Relationship (SAR) of violacein, synthesis of its derivative using benzothiophene instead of indole has been explored. The violacein scaffold is produced in a thermally driven, sequential condensation of an γ-ketoester with ammonium acetate and isatin in polyethylene glycol. This three-component, microwave-mediated cyclization has been utilized to synthesize and characterize a benzothiophene analog of violacein.
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Kim, Seoyoung, "Synthesis of Benzothiophene Analogs of Antimicrobial Pigment Violacein" (2015). Senior Projects Spring 2015. 261.
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