Cardiac-slowing amidines containing the 3-thioindole group. Potential antianginal agents

MJ Zelesko, DF McComsey, WE Hageman…

Index: Zelesko, Michael J.; McComsey, David F.; Hageman, William E.; Nortey, Samuel O.; Baker, Carol A.; Maryanoff, Bruce E. Journal of Medicinal Chemistry, 1983 , vol. 26, # 2 p. 230 - 237

Full Text: HTML

Citation Number: 10

Abstract

Scheme I. Indole I was reacted with thiourea and Iz/KI, and the thiouronium intermediate product was immediately hydrolyzed with aqueous NaOH to give sodium 3-indolylthiolate I1 in situ.'l The thiolate was alkylated with chloroacetonitrile to give nitrile 111. If desired, N- alkylation could be conducted at this point by reaction of nitrile I11 with an alkyl halide and aqueous NaOH, giving alkylated nitriles IV. Reduction of I11 or IV with BH3. THFlZ or ...