24461-61-8Relevant articles and documents
Enantioselective ammonolysis of phenylglycine methyl ester with lipase-pluronic nanoconjugate in tertiary butanol
Wu, Xiaoling,Wang, Rui,Zhang, Yifei,Ge, Jun,Liu, Zheng
, p. 1407 - 1410 (2014)
Asymmetrical ammonolysis of (R)- and (S)-phenylglycine methyl ester was carried out by using a lipase (CALB)-polymer (Pluronic) nanoconjugate as the catalyst, displaying a 11-fold increased catalytic rate compared to the free CALB in tertiary butanol. Graphical Abstract: The asymmetrical ammonolysis of (R)- and (S)-phenylglycine methyl ester was accomplished using a lipase-Pluronic nanoconjugate, displaying a 11-fold higher catalytic rate compared to the free lipase.[Figure not available: see fulltext.]
Dynamic kinetic resolution of phenylglycine esters via lipase-catalysed ammonolysis
Wegman,Hacking,Rops,Pereira,Van Rantwijk,Sheldon
, p. 1739 - 1750 (1999)
Ammonolysis of D,L-phenylglycine methyl ester catalysed by Novozym 435 at 40°C in tert-butyl alcohol gave D-phenylglycine amide in 78% ee at 46% conversion, corresponding to an enantiomeric ratio (E) of 16. Lowering the temperature improved the enantioselectivity (E = 52 at -20°C). Combination of ammonolysis with pyridoxal-catalysed in situ racemisation of the unconverted ester (dynamic kinetic resolution), at -20°C, gave D- phenylglycine amide with 88% ee at 85% conversion. The amide racemised much slower than the ester at this low temperature.
Rubrosides A-H, new bioactive tetramic acid glycosides from the marine sponge Siliquariaspongia japonica
Sata,Wada,Matsunaga,Watabe,Van Soest,Fusetani
, p. 2331 - 2339 (1999)
Eight new tetramic acid glycosides named rubrosides A-H have been isolated from the marine sponge Siliquariaspongia japonica. Their structures were elucidated on the basis of spectral data as tetramic acid glycosides containing polyenes terminating in a 4-chloro-2-methyltetrahydrofuran ring. The absolute stereochemistry of the furan functionality in the two major metabolites, rubrosides D and F, was determined by the NMR method using chiral anisotropic reagents for tetrahydro-2-furoic acid derived by RuO4 oxidation. The absolute stereochemistry of tetramic acid and of the sugar moieties in all rubrosides was deduced by chiral GC analysis of chemical degradation products. The rubrosides induced numerous large intracellular vacuoles in 3Y1 rat fibroblasts at concentrations of 0.5-1.0 μg/mL, and rubrosides A, C, D, and E were cytotoxic against P388 murine leukemia cells with IC50 values of 0.046-0.21 μg/mL. Most rubrosides show antifungal activity against Aspergillus fumigatus and Candida albicans.
Direct reductive amination of ketones with ammonium salt catalysed by Cp*Ir(iii) complexes bearing an amidato ligand
Dai, Zengjin,Pan, Ying-Min,Wang, Shou-Guo,Yin, Qin,Zhang, Xumu
supporting information, p. 8934 - 8939 (2021/11/04)
A series of half-sandwich Ir(iii) complexes1-6bearing an amidato bidentate ligand were conveniently synthesized and applied to the catalytic Leuckart-Wallach reaction to produce racemic α-chiral primary amines. With 0.1 mol% of complex1, a broad range of ketones, including aryl ketones, dialkyl ketones, cyclic ketones, α-keto acids, α-keto esters and diketones, could be transformed to their corresponding primary amines with moderate to excellent yields (40%-95%). Asymmetric transformation was also attempted with chiral Ir complexes3-6, and 16% ee of the desired primary amine was obtained. Despite the unsatisfactory enantio-control achieved so far, the current exploration might stimulate more efforts towards the discovery of better chiral catalysts for this challenging but important transformation.
Development of potent dual PDK1/AurA kinase inhibitors for cancer therapy: Lead-optimization, structural insights, and ADME-Tox profile
Bacci, Andrea,Chiarugi, Sara,Gado, Francesca,Garau, Gianpiero,Gul, Sheraz,Huguet, Samuel,Manera, Clementina,Margheritis, Eleonora,Rapposelli, Simona,Rezai, Keyvan,Riveiro, Maria E.,Runfola, Massimiliano,Sestito, Simona,Vazquez, Ramiro
supporting information, (2021/10/08)
We report the synthesis of novel first-in-class 2-oxindole-based derivatives as dual PDK1-AurA kinase inhibitors as a novel strategy to treat Ewing sarcoma. The most potent compound 12 is suitable for progression to in vivo studies. The specific attributes of 12 included nanomolar inhibitory potency against both phosphoinositide-dependent kinase-1 (PDK1) and Aurora A (AurA) kinase, with acceptable in vitro ADME-Tox properties (cytotoxicity in 2 healthy and 14 hematological and solid cancer cell-lines; inhibition of PDE4C1, SIRT7, HDAC4, HDAC6, HDAC8, HDAC9, AurB, CYP1A2, CYP2C9, CYP2C19, CYP2D6, and hERG). X-ray crystallography and docking studies led to the identification of the key AurA and PDK1/12 interactions. Finally, in vitro drug-intake kinetics and in vivo PK appear to indicate that these compounds are attractive lead-structures for the design and synthesis of PDK1/AurA dual-target molecules to further investigate the in vivo efficacy against Ewing Sarcoma.
