Application of spin labeling to drug assays. III. [15N, 2H13]2,2,5,5-tetramethylpyrroline-1-oxyl-3-carboxylic acid coupled to phenytoin

✍ Scribed by Yul Yost; Carl F. Polnaszek; Jordan L. Holtzman

• Publisher: John Wiley and Sons
• Year: 1983
• Tongue: French
• Weight: 475 KB
• Volume: 20
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580200605

✦ Synopsis

Phorone and [2H14]phorone w e r e c y c l i z e d w i t h 15NH3 o r t o [ l5N]-o r [ 15N,2B17]-4-oxo-2,2,6,6-tetramethyl-15N2H3 p i p e r i d i n e which w e r e t h e n brominated a t C-3 and C-5. Ring c o n t r a c t i o n t h e n gave 2,2,5,5-tetramethyl~~rroline -3carboxamide, which w i t h H 2 0 2 gave t h e corresponding n i t r o xi d e . H y d r o l y s i s i n b a s e of t h e doubly l a b e l e d n i t r o x i d e t h e n gave [ 5N,2H] 2,2,5,5-tetramethylpyrroline-l-oxyl-3c a r b o x y l i c a c i d . The l a t t e r , when coupled t o phenytoin, a f f o r d e d a s p i n -l a b e l e d drug of h i g h s e n s i t i v i t y f o r d e t e ct i o n by ESR technique.

I f t h e s y n t h e s i s w a s s t a r t e d w i t h [ 2 H 1 ~] p h o r o n e , n e g l i g i b l e l o s s of deuterium w a s noted i n t h e f i n a l product even when p r o t i a t e d r e a g e n t s w e r e used.