Solid phase organic synthesis (SPOS): a novel route to diketopiperazines and diketomorpholines.
The solid phase synthesis of libraries containing a 1,3,4,6-tetrasubstituted-2,5-diketo-1,4-piperazine scaffold (DKP) or a 3,4,6-trisubstituted-2,5-diketo-1,4-morpholine scaffold (DKM) from alpha-bromocarboxylic acids and amines is described. Using a design strategy which we refer to as divergent library design, both templates were prepared from a common intermediate. The general utility of this synthetic route in creating novel, non-peptidyl chemical libraries is discussed.
Scott
B O
BO
Chiron Corporation, Emeryville, CA 94806, USA.
Siegmund
A C
AC
Marlowe
C K
CK
Pei
Y
Y
Spear
K L
KL
D002625:Chemistry, Organic; D002851:Chromatography, High Pressure Liquid; D019020:Directed Molecular Evolution / Q000379:methods*; D015195:Drug Design; D008722:Methods; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D055601:Organic Chemistry Phenomena; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D012117:Resins, Synthetic
D009025:Morpholines; D010879:Piperazines; D012117:Resins, Synthetic