1466-83-7Relevant academic research and scientific papers
Inclusion complexes of N-benzoyl-D-leucine and N-benzoyl-L-leucine with β-cyclodextrin by Raman spectroscopy
Spivey, Robin,Swofford, Robert L.
, p. 435 - 438 (1999)
We report what is believed to be the first detection of chiral recognition in the inclusion complexes of cyclodextrins by Raman spectroscopy. The spectra of inclusion complexes of N-benzoyl-D-leucine or N-benzoyl-L-leucine with β-cyclodextrin were recorded in the 1500-1800 and 3000-3150 cm-1 regions. These chiral molecules were chosen to provide group frequencies (NH2(+) and benzoyl C=O) near the chiral center of the guest as well as COO- and phenyl CH for probing the guest molecule without spectral interference from the vibrational bands of the cyclodextrin host. Frequency shifts and intensity decreases were observed for some Raman bands of N-benzoyl-leucines upon inclusion in the cyclodextrin cavity. In the Raman spectra of the inclusion complex, the frequency shifts were greater for N-benzoyl-D-leucine than for N-benzoyl-L-leucine.
Synthesis, characterization, and cytotoxicity of complexes of platinum(u) with 2,2'-bipyridine and N-benzoyl-L-amino acid dianion
Zhang, Jinchao,Zhang, Fangfang,Wang, Liwei,Du, Jianlong,Wang, Shuxiang,Li, Shenghui
, p. 2159 - 2169 (2012)
Four new platinum(II) complexes (1-4) with N-benzoyl-L-amino acid and bipy were synthesized and characterized by elemental analysis, IR, UV, 1H NMR, and mass spectra. The crystal structure of 1 was determined by X-ray diffraction analysis. Cytotoxicities were measured by MTT and SRB assays. Complexes 1-4 exert cytotoxicity with selectivity against HL-60, Bel-7402, BGC-823, and KB cell lines. This suggests that amino acids and acylated groups have important effects on cytotoxicity; the cytotoxicity is also related to the species of tumor cells, but the IC50 values do not show definite correlation with the variation of amino acids and acylated groups.
Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes
Chen, Jian,Zhu, Shaolin
supporting information, p. 14089 - 14096 (2021/09/13)
A nickel-catalyzed, multicomponent regio- and enantioselective coupling via sequential hydroformylation and carbonylation from readily available starting materials has been developed. This modular multicomponent hydrofunctionalization strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes to produce a wide variety of unsymmetrical dialkyl ketones bearing a functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It uses chiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization of complex molecules.
A Facile Approach to the Synthesis of Benzothiazoles from N-Protected Amino Acids
Arfan, M.,Fatima, T.,Mannan, A.,Tahira, A.
, p. 292 - 297 (2020/04/21)
Abstract: –A simple trituration method for the synthesis of 2-substituted benzothiazoles derived from N-protected amino acids and 2-aminothiophenol using molecular iodine as a mild Lewis acid catalyst has been proposed. The reaction occurs in one step for 20–25 min in solve-free conditions and provides the target products in excellent yields.
Rh(iii)-Catalyzed diastereoselective transfer hydrogenation: An efficient entry to key intermediates of HIV protease inhibitors
Chen, Gen-Qiang,Lang, Qi-Wei,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie,Wang, Fangyuan,Wu, Ting,Yin, Congcong,Zhang, Xumu,Zheng, Long-Sheng
, p. 3119 - 3122 (2020/03/23)
A highly efficient diastereoselective transfer hydrogenation of α-aminoalkyl α′-chloromethyl ketones catalyzed by a tethered rhodium complex was developed and successfully utilized in the synthesis of the key intermediates of HIV protease inhibitors. With the current Rh(iii) catalyst system, a series of chiral 3-amino-1-chloro-2-hydroxy-4-phenylbutanes were produced in excellent yields and diastereoselectivities (up to 99% yield, up to 99?:?1 dr). Both diastereomers of the desired products could be efficiently accessed by using the two enantiomers of the Rh(iii) catalyst.
GRANZYME B DIRECTED IMAGING AND THERAPY
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Page/Page column 82; 99, (2019/09/04)
Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.
Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones
Xie, Lihua,Dong, Shunxi,Zhang, Qian,Feng, Xiaoming,Liu, Xiaohua
supporting information, p. 87 - 90 (2019/01/03)
The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.
STRUCTURE AND SYNTHESIS OF HIGHLY FLUORINATED AMINO ACID DERIVATIVES
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Paragraph 0164; 0165; 0166; 0169, (2018/09/19)
Methods of synthesizing polyfluorinated amino acid derivatives are disclosed, along with polyfluorinated amino acid derivatives produced from said methods, as well as compositions containing same. The synthesis methods utilize an oxazolone and a perfluoroarene to produce the polyfluorinated amino acid derivatives.
Formation of Non-Natural α,α-Disubstituted Amino Esters via Catalytic Michael Addition
Teegardin, Kip A.,Gotcher, Lacey,Weaver, Jimmie D.
supporting information, p. 7239 - 7244 (2018/11/25)
The enolate monoanion of amino esters is explored, and the first catalytic Michael addition of α-amino esters is demonstrated. These studies indicate that the acidity of the αC-H is the primary factor determining reactivity. Thus, polyfluorophenylglycine amino esters yield novel α-amino esters in the presence of a catalytic amount of a guanidine-derived base and Michael acceptors. Reactivity requires an acidic N-H, which is accomplished using common protecting groups such as N-Bz, N-Boc, and N-Cbz. Calculations and labeling experiments provide insight into the governing principles in which a key C-to-N proton transfer occurs, resulting in an expansion of the scope to include a number of natural amino esters. The study culminates with a late-stage functionalization of peptidic γ-secretase inhibitor, DAPT.
Optimization of dipeptidic inhibitors of cathepsin L for improved Toxoplasma gondii selectivity and CNS permeability
Zwicker, Jeffery D.,Diaz, Nicolas A.,Guerra, Alfredo J.,Kirchhoff, Paul D.,Wen, Bo,Sun, Duxin,Carruthers, Vern B.,Larsen, Scott D.
supporting information, p. 1972 - 1980 (2018/04/14)
The neurotropic protozoan Toxoplasma gondii is the second leading cause of death due to foodborne illness in the US, and has been designated as one of five neglected parasitic infections by the Center for Disease Control and Prevention. Currently, no trea
