Synthesis of biphenylyltetrazole derivatives of 1-aminopyrroles as angiotensin II antagonists.
Based on preliminary molecular modelling study, the synthesis of two different classes of biphenylyltetrazole derivatives of 1-aminopyrroles, as potentially active non-peptide angiotensin II (AII) antagonists, is reported. Some NH-Boc protected l-aminopyrroles were deprotected, N-acylated, N-alkylated with 5-[4'-bromomethyl-1,1'-biphenyl-2-yl]-1-triphenylmethyl-1H-tetrazo le, and then detritylated to give the first class of title compounds. Other 1-NH-Boc protected 1,2-diaminopyrroles were regioselectively subjected to the 1-alkylation with 5-[4'-bromomethyl-1,1'-biphenyl-2-yl]-1-triphenylmethyl-1H-tetrazo le, to the acylation of the amino group at 2-position of the pyrrole ring, and then to the detritylation process to yield the second class of title compounds.
D000302:Adrenal Cortex / Q000187:drug effects / Q000378:metabolism; D000804:Angiotensin II / Q000037:antagonists & inhibitors* / Q000378:metabolism; D057911:Angiotensin Receptor Antagonists; D000818:Animals; D066298:In Vitro Techniques; D008958:Models, Molecular; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology; D011869:Radioligand Assay; D051381:Rats; D044140:Receptor, Angiotensin, Type 1; D044139:Receptor, Angiotensin, Type 2