39773-44-9Relevant academic research and scientific papers
Kinetic resolution of oxazinones: Rational exploration of chemical space through the design of experiments
Renzi, Polyssena,Kronig, Christel,Carlone, Armando,Er?ksüz, Serap,Berkessel, Albrecht,Bella, Marco
supporting information, p. 11768 - 11775 (2014/10/15)
The organocatalytic kinetic resolution of 4-substituted oxazinones has been optimised (selectivity factor S up to 98, chiral oxazinone ee values up to 99.6% (1a-g) and product ee values up to 90% (3a-g)) in a rational way by applying the Design of Experiments (DoE) approach.
Synthesis, in vitro and in vivo biological evaluation, docking studies, and structure-activity relationship (SAR) discussion of dipeptidyl boronic acid proteasome inhibitors composed of β-amino acids
Zhu, Yongqiang,Zhu, Xinrong,Wu, Gang,Ma, Yuheng,Li, Yuejie,Zhao, Xin,Yuan, Yunxia,Yang, Jie,Yu, Sen,Shao, Feng,Li, Runtao,Ke, Yanrong,Lu, Aijun,Liu, Zhenming,Zhang, Liangren
supporting information; experimental part, p. 1990 - 1999 (2010/08/03)
A series of novel dipeptidyl boronic acid proteasome inhibitors composed of β-amino acids were synthesized, in vitro and in vivo biologically evaluated, and theoretically modeled for the first time. From the screened racemic compounds in enzyme, 4i was the most active. The IC50 value of its pure enantiomer 4q was 9.6 nM, 36-fold more active than its isomer 4p and as active as the marketed bortezomib in inhibiting human 20S proteasome. This candidate also showed good activities with IC50 values nearly less than 5 μM against several human solid and hematologic tumor cell lines. Safety evaluation in vivo with zebrafish and Sprague-Dawley (SD) rats showed that the candidate 4q was less toxic than bortezomib. Pharmacokinetic profiles suggested candidate 4q showed a more plasma exposure and longer half-life than bortezomib. Docking results indicated that 4q nearly interacted with 20S proteasome in a similar way as bortezomib.
Synthesis, in vitro and in vivo biological evaluation, and comprehensive understanding of structure-activity relationships of dipeptidyl boronic acid proteasome inhibitors constructed from β-amino acids
Zhu, Yongqiang,Wu, Gang,Zhu, Xinrong,Ma, Yuheng,Zhao, Xin,Li, Yuejie,Yuan, Yunxia,Yang, Jie,Yu, Sen,Shao, Feng,Lei, Meng
supporting information; experimental part, p. 8619 - 8626 (2011/03/20)
An extensive structure-activity relationship (SAR) study of 72 dipeptidyl boronic acid proteasome inhibitors constructed fromβ -amino acids is reported. SAR analysis revealed that bicyclic groups at the R1 position, 3-F substituents at the Rsu
Kinetic resolution of oxazinones: An organocatalytic approach to enantiomerically pure β-amino acids
Berkessel, Albrecht,Cleemann, Felix,Mukherjee, Santanu
, p. 7466 - 7469 (2007/10/03)
(Chemical Equation Presented) A profitable split: An organocatalytic resolution converts readily available racemic oxazinones 1 into valuable enantiomerically pure β-amino acid derivatives 2 (> 99% ee of the remaining 1 at 53% conversion; 88% ee of the ester 2). This catalytic ring-opening reaction requires as little as 1 mol% of the modular and readily accessible thiourea organocatalyst 3.
