Studies in the design of x-ray contrast agents. Synthesis, hydrophobicity, and solubility of some iodoresorcyl bis(beta-glucosides).
Two diiodo- and two triiodoresorcyl bis(beta-glucosides) were prepared and their hydrophobicity (log P octano) and water solubility were compared to a triiodophenyl beta-glucoside and several experimental nonionic, water-soluble, x-ray contrast agents. The data indicate steric overlap of the halogen substituents by the bulky hydrophilic O-beta-glucosyl substituents; high water solubility is attained only at observed log P octanol approximately 1.5 or lower. Of the new compounds, only 2,4,-6-triiodo-5-N-methylcarboxamidorescorcy bis(beta-glucoside) (6) was highly water soluble. At the physiological pHin dog's plasmia in vitro, compound 6 rapidly hydrolyzed. Poorly water-soluble but more stable compounds of this series were not appreciably absorbed from dog's duodenum.
D000818:Animals; D003287:Contrast Media / Q000138:chemical synthesis*; D004285:Dogs; D005960:Glucosides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis*; D006868:Hydrolysis; D066298:In Vitro Techniques; D007408:Intestinal Absorption; D007700:Kinetics; D012995:Solubility; D013329:Structure-Activity Relationship
D003287:Contrast Media; D005960:Glucosides; D006027:Glycosides