53624-77-4Relevant academic research and scientific papers
General Access to Modified α-Amino Acids by Bioinspired Stereoselective γ-C?H Bond Lactonization
Vicens, Laia,Bietti, Massimo,Costas, Miquel
supporting information, p. 4740 - 4746 (2020/12/25)
α-Amino acids represent a valuable class of natural products employed as building blocks in biological and chemical synthesis. Because of the limited number of natural amino acids available, and of their widespread application in proteomics, diagnosis, drug delivery and catalysis, there is an increasing demand for the development of procedures for the preparation of modified analogues. Herein, we show that the use of bioinspired manganese catalysts and H2O2 under mild conditions, provides access to modified α-amino acids via γ-C?H bond lactonization. The system can efficiently target 1°, 2° and 3° γ-C?H bonds of α-substituted and achiral α,α-disubstituted α-amino acids with outstanding site-selectivity, good to excellent diastereoselectivity and (where applicable) enantioselectivity. This methodology may be considered alternative to well-established organometallic procedures.
Rhodium(II)-catalyzed intramolecular carbonyl ylide formation of α-diazo-β-ketoesters derived from N-phthaloyl-α-amino acids
Enssle, Marc,Buck, Stefan,Werz, Roland,Maas, Gerhard
, p. 149 - 171 (2013/09/24)
Starting from L-alanine, L-phenylalanine, L-leucine, L -norleucine, or L-isoleucine, 2-diazo-3-oxo-4-phthalimido-alkanoates 8 were prepared in three steps. Considerable racemization occurred at the stage of the 3-oxo-4-phthalimido-alkanoates 7. Dirhodium tetraacetate effectively catalyzed the intramolecular formation of carbonyl ylides 9, which in the absence of a trapping reagent underwent a [3+3] cycloaddition reaction to form the dimers 10. Carbonyl ylides 9 underwent [3+2] cycloaddition reactions with several electron-deficient alkenes and alkynes to give oxygen and nitrogen containing multicyclic systems 12-16. The keto group of the αoxy-β-ketoester moiety of cycloadducts 2 and 12 is easily hydrated to give the gem-diol. ARKAT-USA, Inc.
THE 1-BUTYL-2-HYDROXYARALKYL PIPERAZINE DERIVATIVES AND THE USES AS ANTI-DEPRESSION MEDICINE THEREOF
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Page/Page column 14, (2011/08/06)
The invention discloses 1-butyl-2-hydroxyl aralkyl piperazine derivatives and their use as antidepressants. The derivatives of the present invention have triple inhibition effect on the reuptake of 5-HT, NA and DA, and can be administrated to the patients in need thereof in form of composition by route of oral administration, injection and the like. Compared with clinically currently used dual targets antidepressants (such as venlafaxine), said derivatives may have stronger antidepression effect, broader indications, faster onset and lower neurotoxicity and side reaction; and said derivatives have stronger antidepression activity, lower toxicity, higher bioavailability, longer half life and better druggablity, compared with aryl alkanol piperazine derivatives and optical isomers thereof disclosed in prior art. The 1-butyl-2-hydroxyl aralkyl piperazine derivative is the free alkali or its salt of a compound of formula below:
THE 1-BUTYL-2-HYDROXYARALKYL PIPERAZINE DERIVATIVES AND THE USES AS ANTI-DEPRESSION MEDICINE THEREOF
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Page/Page column 18, (2011/08/08)
The invention discloses 1-butyl-2-hydroxyl aralkyl piperazine derivatives and their use as antidepressants. The derivatives of the present invention have triple inhibition effect on the reuptake of 5-HT, NA and DA, and can be administrated to the patients in need thereof in form of composition by route of oral administration, injection and the like. Compared with clinically currently used dual targets antidepressants (such as venlafaxine), said derivatives may have stronger antidepression effect, broader indications, faster onset and lower neurotoxicity and side reaction; and said derivatives have stronger antidepression activity, lower toxicity, higher bioavailability, longer half life and better druggablity, compared with aryl alkanol piperazine derivatives and optical isomers thereof disclosed in prior art. The 1-butyl-2-hydroxyl aralkyl piperazine derivative is the free alkali or its salt of a compound of formula below:
