Synthesis of biphenylyltetrazole derivatives of 1-aminopyrroles as angiotensin II antagonists

Based on preliminary molecular modelling study, the synthesis of two differ ent classes of biphenylyltetrazole derivatives of 1-aminopyrroles, as poten tially active non-peptide angiotensin II (AII) antagonists, is reported. So me NH-Boc protected 1-aminopyrroles were deprotected, N-acylated, N-alkylat ed with 5-[4'-bromomethyl-1,1'-biphenyl-2-yl]-1-triphenylmethyl-1H-tetrazol e, and then detritylated to give the first class of title compounds. Other 1-NH-Boc protected 1,2-diaminopyrroles were regioselectively subjected to t he l-alkylation with 5-[4'-bromomethyl-1,1'-biphenyl-2-yl]-1-triphenylmethy l-1H-tetrazole, to the acylation of the amino group at 2-position of the py rrole ring, and then to the detritylation process to yield the second class of title compounds. (C) 1999 Elsevier Science S.A. All rights reserved.