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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Cell Line, Tumor
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Colonic Neoplasms
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Cyclohexenes / chemical synthesis*
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Cyclohexenes / chemistry
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Cyclohexenes / pharmacology
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Drug Screening Assays, Antitumor
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Humans
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Indoles / chemical synthesis*
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Indoles / chemistry
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Indoles / pharmacology
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Kidney Neoplasms
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Structure-Activity Relationship
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Sulfones / chemical synthesis*
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Sulfones / chemistry
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Sulfones / pharmacology
Substances
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Antineoplastic Agents
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Cyclohexenes
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Indoles
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Sulfones