181517-88-4Relevant academic research and scientific papers
Enantiopure 3-Amino-Substituted 1-Indanones, 1-Tetralones, and 1-Benzosuberones via Friedel-Crafts Cyclisation of ω-Aryl-β-benzamido Acids
Davies, Stephen G.,Goddard, Euan C.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
, p. 1541 - 1544 (2015/06/30)
Conjugate addition of enantiopure lithium (R)-N-benzyl-N-(α-methylbenzyl)amide to a range of ω-aryl-α,β-unsaturated esters gives the corresponding ω-aryl-β-amino esters as single diastereoisomers in high yields. Friedel-Crafts cyclisation of the pendant c
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
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.
Asymmetric michael addition of a recyclable chiral amine: Inversion of stereoselectivity caused by the difference of ethereal solvents
Node, Manabu,Hashimoto, Daisuke,Katoh, Takahiro,Ochi, Shunsuke,Ozeki, Minoru,Watanabe, Tsunefumi,Kajimoto, Tetsuya
supporting information; experimental part, p. 2653 - 2656 (2009/05/27)
(Chemical Equation Presented) The Michael addition of a chiral amine [(-)-6] to α,β-unsaturated esters (4) was attained and the stereoselectivity was inverted by changing the solvent from diethyl ether to tetrahydrofuran when α,β-unsaturated esters having an aromatic ring at the β-position were employed. In addition, the chiral auxiliary in the Michael adducts (9A) was facilely removed with N-iodosuccinimide to afford β-amino esters (10A) and 2-methoxy-d-bornylaldehyde (11), which can be reclaimed to the chiral amine (6) by reductive amination.
Parallel synthesis of homochiral β-amino acids
Davies, Stephen G.,Mulvaney, Andrew W.,Russell, Angela J.,Smith, Andrew D.
, p. 1554 - 1566 (2008/02/09)
The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol.
Homochiral lithium amides for the asymmetric synthesis of β-amino acids
Davies, Stephen G.,Garrido, Narciso M.,Kruchinin, Dennis,Ichihara, Osamu,Kotchie, Luke J.,Price, Paul D.,Mortimer, Anne J. Price,Russell, Angela J.,Smith, Andrew D.
, p. 1793 - 1811 (2007/10/03)
Secondary homochiral lithium amides derived from α-methylbenzylamine undergo highly diastereoselective conjugate additions to a range of α,β-unsaturated esters. The corresponding β-amino acids are readily liberated by successive N-debenzylation and ester hydrolysis, furnishing (R)-β-amino butyric acid, (R)-β-amino pentanoic acid, (S)-β-leucine, (R)-β-amino octanoic acid, (S)-β-phenylalanine, (S)-β-tyrosine methyl ether, (S)-β-tyrosine hydrochloride and (S)-β-(2-methoxyphenyl)-β-amino propanoic acid in high yields and high ee. The application of this procedure to the synthesis of the natural products (R)-β-DOPA and (R)-β-lysine is demonstrated. The development of a simplified one-pot reaction protocol applicable to the multi-gram scale synthesis of homochiral β-amino esters is also delineated.
