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. 2011 Aug 15;21(16):4720-3.
doi: 10.1016/j.bmcl.2011.06.081. Epub 2011 Jun 25.

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

Seth Daly  1 , Kathryn Hayden, Indranil Malik, Nikki Porch, Hong Tang, Snezna Rogelj, Liliya V Frolova, Katrina Lepthien, Alexander Kornienko, Igor V Magedov
Affiliations

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

Seth Daly et al. Bioorg Med Chem Lett. .

Abstract

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.

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Figures

Figure 1
Figure 1
The originally assigned erroneous and corrected structures for compound A.
Scheme 1
Scheme 1
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Scheme 6
See this image and copyright information in PMC

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