2-Carbaborane-3-phenyl-1H-indoles—Synthesis via McMurry Reaction and Cyclooxygenase (COX) Inhibition Activity
2-Carbaborane-3-phenyl-1H-indoles—Synthesis via McMurry Reaction and Cyclooxygenase (COX) Inhibition Activity
Laube, M.; Neumann, W.; Scholz, M.; Lönnecke, P.; Crews, B.; Marnett, L. J.; Pietzsch, J.; Kniess, T.; Hey-Hawkins, E.
Cyclooxygenase-2 (COX-2) inhibitors have been in the focus of medicinal chemistry for years and many compounds exhibiting high selectivity and affinity were developed. As carbaboranes represent interesting pharmacophores as phenyl mimetics in drug development, this paper presents the synthesis of carbaboranyl derivatives of COX-2-selective 2,3-disubstituted indoles. Despite the lability of carbaboranes under reducing conditions, 2-carbaborane-3-phenyl-1H-indoles could be synthesized by McMurry cyclization of the corresponding amides. While the meta-carbaboranyl-substituted derivatives (3a-c) lacked COX inhibition activity, the orthocarbaboranyl analog (3d) was active but showed a selectivity shift towards COX-1.
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ChemMedChem 8(2013)2, 329-335
DOI: 10.1002/cmdc.201200455
Cited 24 times in Scopus
Permalink: https://www.hzdr.de/publications/Publ-17851
Publ.-Id: 17851