Design and synthesis of potent and selective inhibitors of integrin VLA-4

S Wattanasin, B Weidmann, D Roche, S Myers…

Index: Wattanasin, Sompong; Weidmann, Beat; Roche, Didier; Myers, Stewart; Xing, Amy; Guo, Qin; Sabio, Michael; Von Matt, Peter; Hugo, Ronald; Maida, Susan; Lake, Philip; Weetall, Marla Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 22 p. 2955 - 2958

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Citation Number: 11

Abstract

... Other analogues were prepared as outlined in Scheme 4. Michael reaction of phenethylamine with ethyl acrylate in methanol at room temperature for 4 h cleanly gave 22, which was coupled with N-t-BOC-l-leucine hydroxysuccinate ester to give 23, after removal of the t-BOC group. Acylation of 23 with bromoacetyl bromide and reaction with isoamylamine gave 24. Acylation of 23 and 24 with 18 followed by ester hydrolysis gave 12 and 13, respectively. ...