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2‐Carbaborane‐3‐phenyl‐1 H ‐indoles—Synthesis via McMurry Reaction and Cyclooxygenase (COX) Inhibition Activity
Author(s) -
Laube Markus,
Neumann Wilma,
Scholz Matthias,
Lönnecke Peter,
Crews Brenda,
Marnett Lawrence J.,
Pietzsch Jens,
Kniess Torsten,
HeyHawkins Evamarie
Publication year - 2013
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201200455
Subject(s) - pharmacophore , selectivity , chemistry , cyclooxygenase , stereochemistry , combinatorial chemistry , enzyme , catalysis , organic chemistry
Cyclooxygenase‐2 (COX‐2) inhibitors have been the focus of medicinal chemistry efforts for years, and many compounds that exhibit high selectivity and affinity have been 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‐1 H ‐indoles could be synthesized by McMurry cyclization of the corresponding amides. Whereas the meta ‐carbaboranyl‐substituted derivatives lacked COX inhibitory activity, an ortho ‐carbaboranyl analogue was active, but showed a selectivity shift toward COX‐1.