alexa Rapid Synthesis of Phenazine-1-Carboxylic Acid Derived
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Research & Reviews: Journal of Medicinal & Organic Chemistry
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Research Article

Rapid Synthesis of Phenazine-1-Carboxylic Acid Derived Small Molecules from Diverse Anilines: Privileged Structures for Discovery

Nicholas G Paciaroni1, Nicholas V Borrero1, James R Rocca1,2 and Robert W Huigens III1*

1Department of Medicinal Chemistry, University of Florida, 1600 SW Archer Rd, Gainesville, FL, 32610, USA

2McKnight Brain Institute, University of Florida, Gainesville, FL, 32610, USA

Corresponding Author:
Robert W Huigens III
Department of Medicinal Chemistry
University of Florida
1600 SW Archer Rd, Gainesville, FL, 32610, USA
Tel: 1-352-273- 7718
E-mail: [email protected]

Received date: 11/09/2015; Accepted date: 18/10/2015; Published date: 25/10/2015

 

Abstract

The development of rapid approaches for the synthesis of privileged scaffold inspired chemical libraries is a driving force in drug discovery. Phenazines demonstrate a diverse array of biological activities (e.g. anticancer, antibacterial, antifungal, etc.) thus we consider the phenazine heterocycle to be a privileged scaffold of importance to drug discovery. Here, we have developed a synthetic approach that allows for the rapid preparation of four diverse derivatives of phenazine-1-carboxylic acid (PCA) in 3 to 4 linear synthetic steps from a single, commercially available aniline. This step-economy focused approach takes advantage of the Jourdan-Ullmann/sodium borohydride ring-closure pathway to synthesize a diverse set of PCA small molecules, followed by the rapid diversification using Curtius rearrangements and a series of amidation reactions to generate a library of 35 diverse phenazines.

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