Synthesis of a radioiodinated analogue of the serotonin 5-HT(2A) receptor ligand RP 62203

John R. Lever; Suzanne M. Johnson

doi:10.1002/(SICI)1099-1344(199802)41:2<143::AID-JLCR63>3.0.CO;2-P

Synthesis of a radioiodinated analogue of the serotonin 5-HT(2A) receptor ligand RP 62203

John R. Lever, Suzanne M. Johnson

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

An analogue of RP 62203 having radioiodine in the 4-position of the 1,8-naphthosultam ring system has been prepared for evaluation as a ligand for the serotonin 5-HT(2A) receptor. Non-radioactive 4-iodo-RP 62203 was synthesized in three steps (20% overall yield) by iodination of 1,8-naphthosultam with iodine monochloride followed by N-alkylation with 1-bromo-3-chloropropane and coupling with 1-(4-fluorophenyl)piperazine. The precursor for radiolabeling was prepared in 83% yield from 4-iodo-RP 62203 and hexamethylditin by palladium-mediated trimethylstannylation. Electrophilic radioiododestannylation gave 4-[¹²⁵I]-Rp 62203 in good isolated yield (80-86%), with high purity (≤ 99.6%) and specific radioactivity (1200-2066 mCi/CLmol).

Original language	English (US)
Pages (from-to)	143-150
Number of pages	8
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	41
Issue number	2
DOIs	https://doi.org/10.1002/(SICI)1099-1344(199802)41:2<143::AID-JLCR63>3.0.CO;2-P
State	Published - Feb 1998
Externally published	Yes

Keywords

RP 62203
Radioiodine
Serotonin receptor

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Radiology Nuclear Medicine and imaging
Drug Discovery
Spectroscopy
Organic Chemistry

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10.1002/(SICI)1099-1344(199802)41:2<143::AID-JLCR63>3.0.CO;2-P

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title = "Synthesis of a radioiodinated analogue of the serotonin 5-HT(2A) receptor ligand RP 62203",

abstract = "An analogue of RP 62203 having radioiodine in the 4-position of the 1,8-naphthosultam ring system has been prepared for evaluation as a ligand for the serotonin 5-HT(2A) receptor. Non-radioactive 4-iodo-RP 62203 was synthesized in three steps (20% overall yield) by iodination of 1,8-naphthosultam with iodine monochloride followed by N-alkylation with 1-bromo-3-chloropropane and coupling with 1-(4-fluorophenyl)piperazine. The precursor for radiolabeling was prepared in 83% yield from 4-iodo-RP 62203 and hexamethylditin by palladium-mediated trimethylstannylation. Electrophilic radioiododestannylation gave 4-[125I]-Rp 62203 in good isolated yield (80-86%), with high purity (≤ 99.6%) and specific radioactivity (1200-2066 mCi/CLmol).",

keywords = "RP 62203, Radioiodine, Serotonin receptor",

author = "Lever, {John R.} and Johnson, {Suzanne M.}",

year = "1998",

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T1 - Synthesis of a radioiodinated analogue of the serotonin 5-HT(2A) receptor ligand RP 62203

AU - Lever, John R.

AU - Johnson, Suzanne M.

PY - 1998/2

Y1 - 1998/2

N2 - An analogue of RP 62203 having radioiodine in the 4-position of the 1,8-naphthosultam ring system has been prepared for evaluation as a ligand for the serotonin 5-HT(2A) receptor. Non-radioactive 4-iodo-RP 62203 was synthesized in three steps (20% overall yield) by iodination of 1,8-naphthosultam with iodine monochloride followed by N-alkylation with 1-bromo-3-chloropropane and coupling with 1-(4-fluorophenyl)piperazine. The precursor for radiolabeling was prepared in 83% yield from 4-iodo-RP 62203 and hexamethylditin by palladium-mediated trimethylstannylation. Electrophilic radioiododestannylation gave 4-[125I]-Rp 62203 in good isolated yield (80-86%), with high purity (≤ 99.6%) and specific radioactivity (1200-2066 mCi/CLmol).

AB - An analogue of RP 62203 having radioiodine in the 4-position of the 1,8-naphthosultam ring system has been prepared for evaluation as a ligand for the serotonin 5-HT(2A) receptor. Non-radioactive 4-iodo-RP 62203 was synthesized in three steps (20% overall yield) by iodination of 1,8-naphthosultam with iodine monochloride followed by N-alkylation with 1-bromo-3-chloropropane and coupling with 1-(4-fluorophenyl)piperazine. The precursor for radiolabeling was prepared in 83% yield from 4-iodo-RP 62203 and hexamethylditin by palladium-mediated trimethylstannylation. Electrophilic radioiododestannylation gave 4-[125I]-Rp 62203 in good isolated yield (80-86%), with high purity (≤ 99.6%) and specific radioactivity (1200-2066 mCi/CLmol).

KW - RP 62203

KW - Radioiodine

KW - Serotonin receptor

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ER -

Synthesis of a radioiodinated analogue of the serotonin 5-HT(2A) receptor ligand RP 62203

Abstract

Keywords

ASJC Scopus subject areas

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