Synthesis of a potential water-soluble radiographic contrast medium, 2, 4, 6-triiodo-3-acetamido-5-N-methylcarboxamidophenyl beta-D-glucopyranoside.
Starting from 3,5-dinitrobenzoic acid, the infinitely water-soluble compound, 2, 4, 6-triiodo-3-acetamido-5-N-Methylcarboxamidophenyl Beta-D-glucopyranoside (9), was synthesized in nine steps. Glucoside 9, the first example of potentially a new class of water-soluble x-ray contrast media, is rapidly excreted from dog's plasma into the urine, unchanged. It has low intravenous toxicity in mice (LD50 = 24.5 g/kg). Thin-layer chromatography of aqueous solutions of 9 revealed first appearance of aglycon 7 after 1 week at room temperature.
D000818:Animals; D003287:Contrast Media / Q000138:chemical synthesis* / Q000378:metabolism / Q000633:toxicity; D004355:Drug Stability; D005960:Glucosides / Q000138:chemical synthesis / Q000378:metabolism / Q000633:toxicity; D007668:Kidney / Q000000981:diagnostic imaging; D007928:Lethal Dose 50; D008297:Male; D051379:Mice; D011859:Radiography
D003287:Contrast Media; D005960:Glucosides