97807-25-5

Usage

InChI:InChI=1/C13H11IN2O.HI/c1-16-8-2-3-10(9-16)13(17)15-12-6-4-11(14)5-7-12;/h2-9H,1H3;1H

Upstream product

• 97807-17-5 N-succinimidyl (1-methyl-3-pyridinio)formate iodide 
• 540-37-4 p-aminoiodobenzene 
• 6283-24-5 4-aminophenylmercuric acetate 

Downstream Products

• 97807-27-7 1-methyl-3-[N-(p-iodophenyl)carbamoyl]-1,4-dihydropyridine 

Relevant academic research and scientific papers

Precursors to radiopharmaceutical agents for tissue imaging

A class of radiolabeled compounds to be used in tissue imaging that exhibits rapid brain uptake, good brain:blood radioactivity ratios, and long retention times. The imaging agents are more specifically radioiodinated aromatic amines attached to dihydropyridine carriers, that exhibit heart as well as brain specificity. In addition to the radiolabeled compounds, classes of compounds are also described that are used as precursors and intermediates in the preparation of the imaging agents.

Evaluation of the brain-specific delivery of radioiodinated (iodophenyl)alkyl-substituted amines coupled to a dihydropyridine carrier

To evaluate the potential usefulness of radioiodinated phenylamines attached to dihydropyridine carriers as a means of brain-specific delivery of radiopharmaceuticals, 1-methyl-3-[N-[β-(4-[125I]iodophenyl)ethyl]carbamoyl]-1,4-dihydropyridine ([125I]-9) and 1-methyl-3-[N-(4-[125I]iodophenyl)carbamoyl[-1,4-dihydropyridine ([125I]-13) have been prepared by dithionite reduction of the corresponding pyridinium precursors, [125I]-8 and [125I]-12, respectively. Formation of 8 involved coupling of (p-aminophenyl)ethylamine with N-succinimidyl (1-methyl-3-pyridinio)formate iodide (4) followed by transformation to the corresponding N-piperidinyl- or (diethylamino)- triazines that were converted to 8 by treatment with HI. Alternatively, 12 was prepared by initial conversion of (4-aminophenyl)mercuric acetate to 4-iodoaniline by treatment with I2 and then coupling with 4. The radioiodinated quaternary products, 8 and 12, showed low brain uptake and low brain to blood ratios, whereas the dihydropyridine analogues. 9 and 13, showed comparatively good brain uptake and good brain to blood ratios in rats. These data demonstrate that dihydropyridine-coupled radiopharmaceuticals can cross the blood-brain barrier and the technique may be useful for the measurement of cerebral blood perfusion.