Expedient Synthesis of Indolo[2,3-b ]quinolines, Chromeno[2,3-b ]indoles, and 3-Alkenyl-oxindoles from 3,3'-Diindolylmethanes and Evaluation of Their Antibiotic Activity against Methicillin-Resistant Staphylococcus aureus

ACS Omega
Chandrasekhar ChallaRavi S Lankalapalli

Abstract

Easily accessible 3,3'-diindolylmethanes (DIMs) were utilized to generate a focused library of indolo[2,3-b]quinolines (2), chromeno[2,3-b]indoles (3), and 3-alkenyl-oxindoles (4) under 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative conditions. DIMs with ortho-NHTosyl (NHTs) phenyl group afforded indolo[2,3-b]quinolines (2), whereas DIMs with ortho-hydroxy phenyl groups yielded chromeno[2,3-b]indoles (3) and 3-alkenyl-oxindoles (4). The mild conditions and excellent yields of the products make this method a good choice to access a diverse library of bioactive molecules from a common starting material. Two optimized compounds 2a and 2n displayed excellent activity against clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA). Compound 2a showed the minimum inhibitory concentration values in the concentration between 1 and 4 μg/mL, whereas compound 2n revealed the values of 1-2 μg/mL. Furthermore, both the compounds were highly bactericidal and capable to kill the MRSA completely within 360 min. Collectively, the results suggested that both compounds 2a and 2n possess enormous potential to be developed as anti-MRSA agents.

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Citations

Feb 7, 2019·Organic & Biomolecular Chemistry·Sandip KundalUmasish Jana
Feb 13, 2019·Chemistry : a European Journal·Yu-Chen HsuRai-Shung Liu
Apr 25, 2019·Chemistry, an Asian Journal·Satoru Hiroto
Nov 18, 2018·Acta Crystallographica. Section E, Crystallographic Communications·Suhaila SapariSiti Aishah Hasbullah
Oct 31, 2019·The Journal of Organic Chemistry·Onnicha KhaikateChutima Kuhakarn

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Methods Mentioned

BETA
NMR
X-ray
column chromatography

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