Syntheses of conformationally constricted molecules as potential NAALADase/PSMA inhibitors

P Ding, MJ Miller, Y Chen, P Helquist, AJ Oliver…

Index: Ding, Pingyu; Miller, Marvin J.; Chen, Yi; Helquist, Paul; Oliver, A. Jayne; Wiest, Olaf Organic Letters, 2004 , vol. 6, # 11 p. 1805 - 1808

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Citation Number: 29

Abstract

Two six-membered ring targeted analogues of PSMA inhibitors (4a and 4b) were designed on the basis of a computational analysis and synthesized.(E, Z)-Diene 10 was subjected to the nitroso Diels-Alder reaction to give the 1, 4-trans six-membered ring adduct, 4a. The cis isomer 4b was derived from similar nitroso cycloaddition reactions with the correspnding (E, E)-diene and separately from cyclohexadiene. The IC50 values of 4a and 4b in a ...