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2005
Organo-phosphorus compounds
S 0080
Microwave-Assisted "Libraries from Libraries" Approach Toward the Synthesis
Allyl- and C-Cyclopropylalkylamides. — An intermediate 20-member library of
32- 163 of
allylic phosphinoyl amides of type (III) (7 derivatives) and cyclopropylalkylamides of
type (VII) and (X) (13 derivatives) is prepared by cascade reactions of alkynes, zirconocene hydrochloride, Me2Zn, and phosphinoyl imines under microwave irradiation
(MW). The MW greatly accelerates these conversions reducing the reaction times from
hours to minutes. The first-generation library is subsequently expanded to a 100-membered library by a series of N-functionalizations, exemplified by amides (V) and (VIII).
The antiestrogenic activity of seventy library members is screened, revealing three
potent lead compounds of a new structural type. — (WIPF*, P.; COLEMAN, C. M.;
JANJIC, J. M.; IYER, P. S.; FODOR, M. D.; SHAFER, Y. A.; STEPHENSON, C. R.
J.; KENDALL, C.; DAY, B. W.; J. Comb. Chem. 7 (2005) 2, 322-330; Dep. Chem.,
Univ. Pittsburgh, Pittsburgh, PA 15260, USA; Eng.) — Klein
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