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Synthesis of 5-[125I]-iodo-zacopride, a new probe for 5-HT3 receptor binding sites

✍ Scribed by M. Ponchant; T. Koscielniak; M. Hamon; H. Gozlan

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
386 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

In an attempt to develop a specific probe of serotonin 5‐HT~3~ receptors, various methods have been investigated to synthesize a radioiodinated derivative of the potent 5‐HT~3~ antagonist zacopride. The direct iodination of 5‐dechloro‐zacopride 2 was performed using NaI in the presence of either chloramine T or iodo‐beads. Irreproducible results or/and low yields were obtained by these methods. A third approach using a less oxidative medium allowed the synthesis of iodo‐zacopride 4 from 2 with N‐iodo‐succinimide or with NaI and N‐chlorosuccinimide. Using this third condition, high yield was obtained (49%). However, the radioiodinated compound was contaminated by some “cold” zacopride also formed during the reaction. A two step synthesis was successful to eliminate “cold” zacopride but in lower yield (2‐10%). Thus, 4‐amino‐2‐methoxy‐benzoate 5 was iodinated and then coupled with 3‐aminoquinuclidine 8 to give 5‐iodo‐zacopride 4. Radioactive synthesis was carried out in the same condition to give 5‐[^125^1]‐iodo‐zacopride 1 with a yield of 98%. The two enantiomers R‐and S‐5‐[^125^1]‐iodo‐zacopride were synthesized by direct iodination.

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