Synthesis and binding affinities of fluoroalkylated raloxifenes

…, JH Lee, KH Chung, JA Katzenellenbogen…

Index: Lee, Kyo Chul; Moon, Byung Seok; Lee, Jae Hak; Chung, Kyoo-Hyun; Katzenellenbogen, John A.; Chi, Dae Yoon Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 17 p. 3649 - 3658

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Citation Number: 38

Abstract

Three fluoroalkylated derivatives (1–3) of the selective estrogen receptor modulator (SERM), raloxifene, have been synthesized. The key step in the synthesis is the C–C bond formation of benzo [b] thiophene and a substituted phenyl group (ring C) using a Stille reaction. The in vitro binding affinities of the substituted raloxifenes 1–3 are 45, 60, 89%, respectively, relative to the affinity of estradiol, which is higher than the affinity of raloxifene itself (25%). ...