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Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity
Journal article   Peer reviewed

Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity

Seth Daly, Kathryn Hayden, Indranil Malik, Nikki Porch, Hong Tang, Snezna Rogelj, Liliya V. Frolova, Katrina Lepthien, Alexander Kornienko and Igor V. Magedov
Bioorganic and Medicinal Chemistry Letters, Vol.21(16)
2011
DOI: https://doi.org/10.1016/j.bmcl.2011.06.081

Abstract

Anti-Bacterial Agents Antifungal Agents Bacteria Diazonium Compounds Fungi Indoles Microbial Sensitivity Tests Molecular Structure Salts Stereoisomerism Structure-Activity Relationship methicillin resistant Staphylococcus aureus diazonium compound indole derivative oxygen penicillin G sulfur vancomycin antibacterial activity antifungal activity antineoplastic activity article arylation chemical reaction drug metabolism drug potentiation drug synthesis human human cell minimum inhibitory concentration structure activity relation
A novel reaction of indole with aryldiazonium salts leading to the formation of 2-aryl-3-(arylazo)indoles was discovered. The products were found to possess potent anti-MRSA and anti-LLVRE activities. The SAR studies indicate that the potentially metabolically labile azo functionality can be replaced with ether oxygen and thioether sulfur atoms without any loss of activity. © 2011 Elsevier Ltd. All rights reserved.

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