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.

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.

• Authors: Andrew J McCarroll, Tracey D Bradshaw, Andrew D Westwell, Charles S Matthews, Malcolm F G Stevens
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 50 Issue 7 Pg. 1707-10 (Apr 05 2007) ISSN: 0022-2623 [Print] United States
• PMID: 17343370 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Cyclohexenes
• Indoles
• Sulfones

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Colonic Neoplasms
• Cyclohexenes (chemical synthesis, chemistry, pharmacology)
• Drug Screening Assays, Antitumor
• Humans
• Indoles (chemical synthesis, chemistry, pharmacology)
• Kidney Neoplasms
• Structure-Activity Relationship
• Sulfones (chemical synthesis, chemistry, pharmacology)