Structure activity studies leading to a tissue-selective hypotensive prostaglandin analog,...

During our systematic search for prostaglandins with improved tissue selectivity and metabolic stability, we synthesized a series of PGE2 analogs in which the n-amyl carbinol side chain was systematically substituted by a phenyl ring, based on structural considerations incorporating the 17,18-cis-double bond of PGE1 into an aromatic ring. These compounds were evaluated for uterine stimulant, bronchodilator and hypotensive activity. Among the divergent biological profiles exhibited by these analogs, noteworthy was the tissue-selective hypotensive profile displayed by 13,14-dihydro-16-phenyl-omega-tetranor PGE2.