Publications [#330256] of Michael J. Therien

Papers Published

1. Gauthier, JY; Jones, T; Champion, E; Charette, L; Dehaven, R; Ford-Hutchinson, AW; Hoogsteen, K; Lord, A; Masson, P; Piechuta, H, Stereospecific synthesis, assignment of absolute configuration, and biological activity of the enantiomers of 3-[[[3-[2-(7-chloroquinolin-2-yl)-(E)-ethenyl]phenyl] [[3-(dimethylamino)-3-oxopropyl]thio]methyl]thio]propionic acid, a potent and specific leukotriene D4 receptor antagonist., Journal of medicinal chemistry, vol. 33 no. 10 (October, 1990), pp. 2841-2845 [doi]
   (last updated on 2026/01/15)

   Abstract:
   The enantiomers of the leukotriene D4 antagonist 3-[[[3-[2-(7-chloroquinolin-2-yl)-(E)-ethenyl]phenyl] [[3-(dimethylamino)-3-oxopropyl]thio]methyl]thio]propionic acid (L-660,711)(MK-571) have been prepared, their absolute stereochemistry has been assigned as S for (+)-1 and R for (-)-1 by X-ray analysis of a synthetic intermediate (5), and the biological activity of the enantiomers has been explored. Unexpectedly, the enantiomers are both comparably biologically active with (+)-1 slightly more intrinsically active at the LTD4 receptor in vitro.