Synthesis and structure-activity relationship of C5-substituted analogs of (.+-.)-10, 11-dihydro-5H-dibenzo [a, d] cyclohepten-5, 10-imine [(.+-.)-desmethyl-MK801]: …

…, A Thurkauf, MV Mattson, AE Jacobson…

Index: Monn; Thurkauf; Mattson; Jacobson; Rice Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1069 - 1076

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Citation Number: 19

Abstract

A series of eight C5-substituted analogues of (*)-lO, ll-dihydro-5Hdibenzo [a, d] cyclohepten- 5, lO-imine (1) have been prepared by the directed lithiation-alkylation (and acylation) of its (*)-N-tert-butylformamidinyl derivative 2 followed by formamidine solvolysis. An additional 10 analogues were prepared by elaboration of the C5-ethyl ester derivative. Analogues possessing large (eg propyl and larger) lipophilic substituents displace [3H]-1-(1- ...