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 |
|---|---|
| Pages (from-to) | 77-90 |
| Number of pages | 14 |
| Journal | Journal of Labelled Compounds and Radiopharmaceuticals |
| Volume | 43 |
| Issue number | 1 |
| DOIs | |
| State | Published - 2000 |
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All Science Journal Classification (ASJC) codes
- Clinical Biochemistry
- Molecular Medicine
- Analytical Chemistry
- Organic Chemistry
- Drug Discovery
- Pharmacology
Cite this
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, 2000, p. 77-90.Research output: Contribution to journal › Article
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TY - JOUR
T1 - 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
AU - Malone, Justin A.
AU - Reidelberger, Roger D.
AU - Hulce, Martin
PY - 2000
Y1 - 2000
N2 - 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.
AB - 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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U2 - 10.1002/(SICI)1099-1344(200001)43:1<77::AID-JLCR292>3.0.CO;2-V
DO - 10.1002/(SICI)1099-1344(200001)43:1<77::AID-JLCR292>3.0.CO;2-V
M3 - Article
AN - SCOPUS:0033966323
VL - 43
SP - 77
EP - 90
JO - Journal of Labelled Compounds and Radiopharmaceuticals
JF - Journal of Labelled Compounds and Radiopharmaceuticals
SN - 0362-4803
IS - 1
ER -