Bioorganic and Medicinal Chemistry Letters p. 2253 - 2258 (1998)
Update date:2022-08-03
Topics:
Goulet, Mark T.
McAlpine, Shelli R.
Staruch, Mary Jo
Koprak, Samuel
Dumont, Francis J.
Cryan, John G.
Wiederrecht, Gregory J.
Rosa, Raymond
Wilusz, Mary Beth
Peterson, Laurence B.
Wyvratt, Matthew J.
Parsons, William H.
A series of C32-O-aralkyl ether derivatives of the FK-506 related macrolide ascomycin have been prepared based on an earlier reported C32-O- cinnamyl ether design. In the present study, the nature of the aryl tethering group was varied in an attempt to improve oral activity. An imidazol-2-yl- methyl tether was found to be superior among those investigated and has resulted in an ascomycin analog, L-733,725, with in vivo immunosuppressive activity comparable to FK-506 but with an improved therapeutic index.
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