Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives
Publication type: Journal Article
Publication date: 2002-02-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Starting with the proteinogenic amino acid ( S )-glutamate ( 3 ) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxopiperazin-2-yl)propionates 6 , 11 , and 14 is presented. Key intermediates in the synthesis of N 1 -benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N -monobenzylglutamate 8 and the chloroacetamide 12 , which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for σ 1 -receptors ( K i =66.1 nM).
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Metrics
25
Total citations:
25
Citations from 2024:
2
(8%)
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MLA
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GOST
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Weigl M., Wünsch B. Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives // Tetrahedron. 2002. Vol. 58. No. 6. pp. 1173-1183.
GOST all authors (up to 50)
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Weigl M., Wünsch B. Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives // Tetrahedron. 2002. Vol. 58. No. 6. pp. 1173-1183.
Cite this
RIS
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TY - JOUR
DO - 10.1016/s0040-4020(01)01212-1
UR - https://doi.org/10.1016/s0040-4020(01)01212-1
TI - Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives
T2 - Tetrahedron
AU - Weigl, Manuela
AU - Wünsch, Bernhard
PY - 2002
DA - 2002/02/01
PB - Elsevier
SP - 1173-1183
IS - 6
VL - 58
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2002_Weigl,
author = {Manuela Weigl and Bernhard Wünsch},
title = {Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives},
journal = {Tetrahedron},
year = {2002},
volume = {58},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/s0040-4020(01)01212-1},
number = {6},
pages = {1173--1183},
doi = {10.1016/s0040-4020(01)01212-1}
}
Cite this
MLA
Copy
Weigl, Manuela, and Bernhard Wünsch. “Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives.” Tetrahedron, vol. 58, no. 6, Feb. 2002, pp. 1173-1183. https://doi.org/10.1016/s0040-4020(01)01212-1.