1197335-24-2Relevant academic research and scientific papers
Conformationally rigid pyrazoloquinazoline α-amino acids: One- And two-photon induced fluorescence
Bell, Jonathan D.,Harkiss, Alexander H.,Nobis, David,Malcolm, Eilidh,Knuhtsen, Astrid,Wellaway, Christopher R.,Jamieson, Andrew G.,Magennis, Steven W.,Sutherland, Andrew
, p. 1887 - 1890 (2020)
The synthesis and photophysical properties of a new class of α-amino acid bearing a rigid pyrazoloquinazoline chromophore are described. Confromational constraint of the amino acid side-chains resulted in high emission quantum yields, while the demonstration of two-photon-induced fluorescence via near-IR excitation signifies their potential for sensitive bioimaging applications.
Synthesis and Fluorescent Properties of β-Pyridyl α-Amino Acids
Harkiss, Alexander H.,Bell, Jonathan D.,Knuhtsen, Astrid,Jamieson, Andrew G.,Sutherland, Andrew
, p. 2879 - 2890 (2019/03/07)
The preparation of a new class of β-pyridyl α-amino acid is described using a highly regioselective, ytterbium-catalyzed hetero-Diels-Alder reaction of enones with vinyl ethers followed by a modified Knoevenagel-Stobbe reaction as the key heterocycle form
Compound and application thereof
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Paragraph 0757, (2016/10/09)
The invention discloses a compound and application thereof. The compound is the compound shown in the formula (I) or a stereoisomer or a pharmaceutical acceptable salt or solvate or a prodrug of the compound shown in the formula (I). The compound can restrain tumor cell proliferation through the effect RRM2, and restrain tumor stem cell regeneration, thereby being effectively used for preparing medicine for preventing or treating proliferative diseases and particularly anti-cancer medicine.
Switching the stereochemical outcome of 6- endo - Trig cyclizations; Synthesis of 2,6- cis -6-substituted 4-oxopipecolic acids
Daly, Mark,Cant, Alastair A.,Fowler, Lindsay S.,Simpson, Graham L.,Senn, Hans Martin,Sutherland, Andrew
, p. 10001 - 10009 (2013/01/15)
A base-mediated 6-endo-trig cyclization of readily accessible enone-derived α-amino acids has been developed for the direct synthesis of novel 2,6-cis-6-substituted-4-oxo-l-pipecolic acids. A range of aliphatic and aryl side chains were tolerated by this mild procedure to give the target compounds in good overall yields. Molecular modeling of the 6-endo-trig cyclization allowed some insight as to how these compounds were formed, with the enolate intermediate generated via an equilibrium process, followed by irreversible tautomerization/neutralization providing the driving force for product formation. Stereoselective reduction and deprotection of the resulting 2,6-cis-6-substituted 4-oxo-l-pipecolic acids to the corresponding 4-hydroxy-l-pipecolic acids was also performed.
A one-pot, reductive amination/6-endo-trig cyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids
Fowler, Lindsay S.,Thomas, Lynne H.,Ellis, David,Sutherland, Andrew
, p. 6569 - 6571 (2011/06/26)
The first stereoselective synthesis of 2,6-trans-6-substituted-4-oxo-l- pipecolic acids using a tandem reductive amination/6-endo-trig cyclisation process is described. The sequential reduction and cyclisation mediated by sodium cyanoborohydride allowed the preparation of a series of highly functionalised 6-alkyl and 6-aryl analogues.
Synthesis of fluorescent enone derived α-amino acids
Fowler, Lindsay S.,Ellis, David,Sutherland, Andrew
supporting information; experimental part, p. 4309 - 4316 (2009/12/06)
The development of a facile and general method for the preparation of enone derived α-amino acids is described. The key step involves a Horner-Wadsworth-Emmons reaction between an aspartic acid derived β-keto phosphonate ester and a range of aldehydes resulting in the formation of highly functionalised α-amino acids in good yields. An efficient two-stage deprotection process using mild conditions was developed to give the parent α-amino acids. Application of this methodology has produced a novel fluorescent α-amino acid that has potential as a biological marker.
