Synthesis of a radoilabeled type A cholecystokinin receptor antagonist, (R)-N-pentyl-N-(4,5-di[3H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide

Justin A. Malone; Roger D. Reidelberger; Martin Hulce

doi:10.1002/(SICI)1099-1344(200001)43:1<77::AID-JLCR292>3.0.CO;2-V

Synthesis of a radoilabeled type A cholecystokinin receptor antagonist, (R)-N-pentyl-N-(4,5-di[³H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide

Justin A. Malone, Roger D. Reidelberger, Martin Hulce

Department of Chemistry

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

3 Scopus citations

Abstract

A method for the preparation of a radiolabeled CCK(A)-specific antagonist, (R)-N-pentyl-N-(4,5-di[³H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide, [³H]-A-65186, is described. (R)-γ-Benzyl-N-BOC-glutamic acid was coupled with N-(4-pentenyl)-N-pentylamine using BOPCl and TEA in dichloromethane to provide the corresponding amide. Deprotection of the α-amino moiety followed by coupling with 3-quinolinecarboxylic acid in the presence of EDCI, TEA, and HOBt in dichloromethane resulted in (R)-N-(4-pentenyl)-N-pentyl γ-benzyl-N(α)-(3-quinolinoyl)glutamic acid amide. Tritiation with concomitant hydrogenolysis of the benzyl ester proceeds smoothly to provide [³H]-A-65186.

Original language	English (US)
Pages (from-to)	77-90
Number of pages	14
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	43
Issue number	1
DOIs	https://doi.org/10.1002/(SICI)1099-1344(200001)43:1<77::AID-JLCR292>3.0.CO;2-V
State	Published - Jan 1 2000

All Science Journal Classification (ASJC) codes

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

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Synthesis of a radoilabeled type A cholecystokinin receptor antagonist, (R)-N-pentyl-N-(4,5-di[³H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide. / Malone, Justin A.; Reidelberger, Roger D.; Hulce, Martin.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 43, No. 1, 01.01.2000, p. 77-90.

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

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abstract = "A method for the preparation of a radiolabeled CCK(A)-specific antagonist, (R)-N-pentyl-N-(4,5-di[3H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide, [3H]-A-65186, is described. (R)-γ-Benzyl-N-BOC-glutamic acid was coupled with N-(4-pentenyl)-N-pentylamine using BOPCl and TEA in dichloromethane to provide the corresponding amide. Deprotection of the α-amino moiety followed by coupling with 3-quinolinecarboxylic acid in the presence of EDCI, TEA, and HOBt in dichloromethane resulted in (R)-N-(4-pentenyl)-N-pentyl γ-benzyl-N(α)-(3-quinolinoyl)glutamic acid amide. Tritiation with concomitant hydrogenolysis of the benzyl ester proceeds smoothly to provide [3H]-A-65186.",

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