Photochemically activated antiviral halogenated 1,8-naphthalimides: Synthesis of N, N′-BIS-{2-[(5-bromo-2-[1-14C]hexyl-1H-benz[DE]isoquinolin-1,3(2H)-dion-6-YL)amino]ethyl}hexanediamide
✍ Scribed by Brendan A. Hayes; Surendra Gupta; Shao-Chieh Chang; Ronald E. Utecht; David E. Lewis
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- French
- Weight
- 267 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
The synthesis of N,"-bis- (2-[(5-bromo-2-[ 1-14CIhexyl-1H-benz[de]isoquinolin-1,3(2H)-dion-6-yl)amino]ethyl}hexanediamide from 1-[ l-14C]-hexylamine and 4chloro-1 &naphthalic anhydride is described. The anhydride is first converted to the 4-chloro-N-[ 1-14C]hexyl-l,8-naphthalimide (2) by condensation with 1-[ 1-14C]-hexylamine, and the chlorine is then displaced with ethylenediamine to give the 4-(2-aminoethylamino-N-[ l-14C]hexyl-l ,8-naphthalimide a. Coupling of this monomeric naphthalimide with adipoyl chloride affords the dimeric naphthalimide (a which is brominated regiospecifically with elemental bromine in carbon tetrachloride to afford the title compound a.