Chemistry Publications
Document Type
Article
Publication Date
9-15-2014
Journal
Canadian Journal of Chemistry
Volume
93
Issue
2
First Page
207
Last Page
217
URL with Digital Object Identifier
doi:10.1139/cjc-2014-0265
Abstract
A highly cross-linked polystyrene resin bearing a reactive chlorostannane moiety 1 has been used to generate a variety of arylstannane radiopharmaceutical precursors for no-carrier-added radioiodination. The resins were characterized for their solvent compatibility and sensitivity to acid cleavage. Resin-supported arylstannanes synthesized via their aryl lithium analogues include 3- and 4-stannylbenzaldehydes, 3- and 4-stannylbenzoic acids, and 3- and 4-N-succinimidyl benzoates. A three-step route to the resin-supported stannylbenzoic acids 12a/b was developed through resin-supported benzaldehydes 11a/b. The aldehyde to acid conversion efficiency is >90%, and acid loading capacities of 0.66–0.94 mmol/g were obtained. Resin-supported N-succinimidyl benzoates 16a/b were prepared from the acid with 78%–84% conversion efficiency. Libraries of resin-supported benzamides 19a/b prepared from amine conjugation to corresponding benzoic acids or N-succinimidyl benzoates are described. A third approach describes the preparation of resin-supported benzamides via direct conjugation of the dilithio salt of the intact benzamide to the chlorostannane resin 1. Lastly, as proof-of-principle, a radiolabeling study with iodine-131 (131I) was performed with a resin-supported benzamide to afford the corresponding radioligand in moderate yields, and high radiochemical purity.
Notes
The full text document submitted does not include the figures and tables that are included with the original paper that was published. They were included in the "supplemental"section but are part of the main manuscript.