1. Academic Validation
  2. Quinols as novel therapeutic agents. 7.1 Synthesis of antitumor 4-[1-(arylsulfonyl-1H-indol-2-yl)]-4-hydroxycyclohexa-2,5-dien-1-ones by Sonogashira reactions

Quinols as novel therapeutic agents. 7.1 Synthesis of antitumor 4-[1-(arylsulfonyl-1H-indol-2-yl)]-4-hydroxycyclohexa-2,5-dien-1-ones by Sonogashira reactions

  • J Med Chem. 2007 Apr 5;50(7):1707-10. doi: 10.1021/jm061163m.
Andrew J McCarroll 1 Tracey D Bradshaw Andrew D Westwell Charles S Matthews Malcolm F G Stevens
Affiliations

Affiliation

  • 1 Centre for Biomolecular Sciences, School of Pharmacy, University of Nottingham, University Park, Nottingham, Nottingham, NG7 2RD, United Kingdom.
Abstract

Interaction of 2-iodoaniline or 5-fluoro-2-iodoaniline with a range of arylsulfonyl chlorides affords sulfonamides that undergo Sonogashira couplings under thermal or microwave conditions with the alkyne 4-ethynyl-4-hydroxycyclohexa-2,5-dien-1-one followed by cyclization to 4-[1-(arylsulfonyl-1H-indol-2-yl)]-4-hydroxycyclo-hexa-2,5-dien-1-ones. This method allows for incorporation of a range of substituents into the arylsulfonyl moiety, and compounds showed selective in vitro inhibition of Cancer cell lines of colon and renal origin, a feature of compounds bearing the quinol pharmacophore.

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