67364-91-4Relevant academic research and scientific papers
11,12-Secoprostaglandins. 6. Interphenylene Analogues of Acylhydroxyalkanoic Acids and Related Compounds as Renal Vasodilators
Bicking, John B.,Robb, Charles M.,Cragoe, Edward J.,Blaine, Edward H.,Watson, L. Sherman,Dunlay, Mary C.
, p. 335 - 341 (2007/10/02)
The synthesis is described of a series of interphenylene analogues of the modified 11,12-secoprostaglandins and their sulfonamide isosteres on which we have reported previously.The new compounds are formally derived from members of earlier series by replacement of segments of the methylene chains by phenylene units.Several of these compounds displayed renal vasodilatory activity on iv stat administration to anesthetized dogs. 4-(4-Acetyl-8-hydroxytridecyl)benzoic acid tested additionally in conscious dogs orally caused a significant increase in renal blood flow at 5 mg/kg.
Interphenylene 11,12-secoprostaglandins
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, (2008/06/13)
Novel interphenylene derivatives of 11,12-secoprostaglandins are prepared by the stepwise alkylation of the ethyl ester or the t-butyl ester of acetoacetic acid. One such method involves treatment of the t-butyl ester of acetoacetic acid with a strong base to form the anion followed by treatment with ethyl p-(3-bromopropyl)benzoate to produce ethyl 4-(4-tert-butoxycarbonyl-5-oxo-hexyl)benzoate, subsequently reacting the anion of the thus-formed benzoate with 1-chloro-4-acetoxynonane to produce ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridecyl)benzoate followed by decarboxylation and alkaline hydrolysis to produce the desired product 4-(4-acetyl-8-hydroxytridecyl)benzoic acid which is useful as a pharmaceutical in the treatment of patients with renal failure and in the prevention of transplant rejection.
