Prostaglandins and congeners. IX. The synthesis of 15-deoxy-16-, 17-, or 20-hydroxyprostaglandins and 15-deoxy-15-hydroxymethylprostaglandin E2.
Prostaglandin congeners wherein the 15-hydroxy group is moved to the C16, C17, or C20 position or is replaced by a hydroxymethyl group were prepared via the 1, 4-addition of a lithium trialkyl-trans-alkenyl alanate to an appropriate cyclopentenone. Several of the 16-hydroxy derivatives showed significant activity as constrictors of the isolated gerbil colon and in bronchodilator and anti-secretory assays.
D000818:Animals; D001980:Bronchi / Q000187:drug effects; D003106:Colon / Q000187:drug effects; D005750:Gastric Juice / Q000378:metabolism; D005849:Gerbillinae; D006168:Guinea Pigs; D008968:Molecular Conformation; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D011453:Prostaglandins / Q000138:chemical synthesis* / Q000494:pharmacology; D011458:Prostaglandins E / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats; D012636:Secretory Rate / Q000187:drug effects
D011453:Prostaglandins; D011458:Prostaglandins E