The synthesis of chiral 3-oxo-6-[(phenylmethoxy)-carbonyl]-2-piperazineacetic acid esters designed for the presentation of an aspartic acid side chain. A subsequent novel Friedel Crafts reaction

doi:10.1016/S0040-4039(00)60843-2

Paper

DOI: 10.1016/S0040-4039(00)60843-2

The synthesis of chiral 3-oxo-6-[(phenylmethoxy)-carbonyl]-2-piperazineacetic acid esters designed for the presentation of an aspartic acid side chain. A subsequent novel Friedel Crafts reaction

Published Nov 17, 1992 · T. Kogan, T. Rawson

Tetrahedron Letters

Q3 SJR score

Citations

Influential Citations

Full textSemantic Scholar

Abstract

Abstract hidden due to publisher request; this does not indicate any issues with the research. Click the full text link above to read the abstract and view the original source.

Study Snapshot

This study presents a novel Friedel Crafts reaction for synthesizing chiral 3-oxo-6-[(phenylmethoxy)carbonyl]-2-piperazineacetic acid esters with an aspartic acid side chain, resulting in unexpected tricyclic products.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Full text analysis coming soon...

References

DOI: 10.1016/0040-4039(92)88173-3

3,6-dioxoperhydropyrrolo[1,2-a]pyrazines. A new approach to conformationally restricted tripeptides

Catalytic hydrogenation of 4-ketodiesters from Z-Xaa-Gly halomethyl ketones and dimethyl malonate leads to highly stereocontrolled Xaa-Gly-Phe restricted tripeptides.

1992·9citations·M. Martín-Martínez et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.1016/S0040-4020(01)88534-3

Synthesis of cyclic ketomethylene dipeptide derivatives

Cyclic ketomethylene dipeptide derivatives, derived from L-Phe and L-Trp, have been synthesized, with 3-substituted analogues containing Phe, Asp, and Ala side chains.

1992·4citations·M. Domínguez et al.·Tetrahedron

Tetrahedron

DOI: 10.1021/JO00009A016

Conformationally restricted arginine analogs

Conformationally constrained protected arginine analogues can be useful as stable replacements for bioactive peptides and probes for understanding protein-peptide interactions.

1991·51citations·T. Webb et al.·Journal of Organic Chemistry

Journal of Organic Chemistry

DOI: 10.1002/JPS.2600790519

Synthesis and biological activity of a series of aspartate transcarbamoylase inhibitors: N-substituted diethyl aspartates and N-substituted-3-oxo-1,4-piperazine-2-acetic acid esters.

N-substituted diethyl aspartates and 3-oxo-1,4-piperazine-2-acetic acid esters show potential as aspartate transcarbamoylase inhibitors, with some showing antimicrobial activity and specificity against tumor cells.

1990·9citations·P. Dutta et al.·Journal of pharmaceutical sciences

Journal of pharmaceutical sciences

DOI: 10.1021/JM00119A019

Design and synthesis of somatostatin analogues with topographical properties that lead to highly potent and specific mu opioid receptor antagonists with greatly reduced binding at somatostatin receptors.

Our somatostatin analogues show high affinity and selectivity for mu opioid receptors, with minimal or no somatostatin-like activity.

1988·113citations·W. Kazmierski et al.·Journal of medicinal chemistry

Journal of medicinal chemistry

DOI: 10.1002/HLCA.19850680322

The Structure of Pyroergotamine

Pyroergotamine's molecular structure reveals that its puzzling spectroscopic and chemical properties are due to crowding within the molecule.

1985·9citations·Roberata O. Day et al.·Helvetica Chimica Acta

Helvetica Chimica Acta

DOI: 10.1021/JM00243A011

Studies in potential filaricides. 6. Synthesis of 3,8-disubstituted 1,3,8-triazabicyclo(4.4.0)decan-2-ones and -thiones.

Some 1,3,8-triazabicyclo[4.4.0]decan-2-ones and -thiones show moderate microfilaricidal activity against Litomosoides carinii in cotton rats.

1975·18citations·S. Sharma et al.·Journal of medicinal chemistry

Journal of medicinal chemistry

Citations

DOI: 10.1002/psc.2968

Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides

This study demonstrates that multigram quantities of Fmoc azido amino acids can be prepared within a week or two at user-friendly costs, enabling the synthesis of azidopeptides at a lower cost.

2017·16citations·J. Pícha et al.·Journal of Peptide Science

Journal of Peptide Science

DOI: 10.1007/s00726-011-1145-2

Stable triazolylphosphonate analogues of phosphohistidine

This study presents the design and synthesis of stable triazolylphosphonate analogues of N1- and N3-phosphohistidine, suitable for bioconjugation, to improve the study of potential drug targets in cell signaling pathways.

2011·23citations·S. Mukai et al.·Amino Acids

Amino Acids

DOI: 10.1039/b908548c

Facile synthesis of structurally diverse 5-oxopiperazine-2-carboxylates as dipeptide mimics and templates.

This study presents a facile method for synthesis of diverse 5-oxopiperazine-2-carboxylates as dipeptide mimics and templates in 39-99% yields, with a preference for trans-configured 6-phenyl-5-oxopiperazine-2-carboxylates.

2009·10citations·Michael Limbach et al.·Organic & biomolecular chemistry

Organic & biomolecular chemistry

DOI: 10.1016/J.TETLET.2007.07.078

An efficient synthesis of optically pure α-alkyl-β-azido- and α-alkyl-β-aminoalanines via ring opening of 3-amino-3-alkyl-2-oxetanones

This study presents an efficient synthesis of optically pure -alkyl--azido- and -alkyl--aminoalanines via ring opening of 3-amino-3-alkyl-2-oxetanones, suitable for direct incorporation

2007·8citations·A. Kudaj et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.1016/J.TETLET.2006.10.044

Highly diastereoselective Staudinger reaction on 5,6-dihydropyrazin-2-(1H)-ones. Synthesis of enantiopure fused oxopiperazino-β-lactams

The Staudinger reaction effectively synthesizes enantiopure fused oxopiperazino--lactams with no epimerization, producing 2-oxopiperazine-3-acetic acid derivatives in good yields.

2006·13citations·A. Viso et al.·Tetrahedron Letters

Tetrahedron Letters