123761-13-7Relevant academic research and scientific papers
EIF4E INHIBITORS AND USES THEREOF
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, (2021/09/11)
The present invention provides compounds inhibiting elF4E activity and compositions and methods of using thereof.
Chemical assembly systems: Layered control for divergent, continuous, multistep syntheses of active pharmaceutical ingredients
Ghislieri, Diego,Gilmore, Kerry,Seeberger, Peter H.
supporting information, p. 678 - 682 (2015/03/04)
While continuous chemical processes have attracted both academic and industrial interest, virtually all active pharmaceutical ingredients (APIs) are still produced by using multiple distinct batch processes. To date, methods for the divergent multistep continuous production of customizable small molecules are not available. A chemical assembly system was developed, in which flow-reaction modules are linked together in an interchangeable fashion to give access to a wide breadth of chemical space. Control at three different levels - choice of starting material, reagent, or order of reaction modules - enables the synthesis of five APIs that represent three different structural classes (γ-amino acids, γ-lactams, β-amino acids), including the blockbuster drugs Lyrica and Gabapentin, in good overall yields (49-75%).
Aminomethylation of enals through carbene and acid cooperative catalysis: Concise access to β2-amino acids
Xu, Jianfeng,Chen, Xingkuan,Wang, Ming,Zheng, Pengcheng,Song, Bao-An,Chi, Yonggui Robin
, p. 5161 - 5165 (2015/04/27)
A convergent, organocatalytic asymmetric aminomethylation of α,β-unsaturated aldehydes by N-heterocyclic carbene (NHC) and (in situ generated) Bronsted acid cooperative catalysis is disclosed. The catalytically generated conjugated acid from the base plays dual roles in promoting the formation of azolium enolate intermediate, formaldehyde-derived iminium ion (as an electrophilic reactant), and methanol (as a nucleophilic reactant). This redox-neutral strategy is suitable for the scalable synthesis of enantiomerically enriched β2-amino acids bearing various substituents. Harmonious cooperation: An N-heterocyclic carbene (NHC) and (in situ generated) Bronsted acid cooperatively catalyze the aminomethylation of α,β-unsaturated aldehydes. This cooperative catalytic reaction provides a redox neutral strategy for quick access to β2-amino esters in an enantioselective manner.
Synthesis of chiral β2-amino acids by asymmetric hydrogenation
Luehr, Susan,Holz, Jens,Zayas, Odalys,Wendisch, Volkmar,Boerner, Armin
, p. 1301 - 1319 (2012/11/07)
The synthesis of chiral β2-amino acids by homogeneous asymmetric hydrogenation is discussed. Prochiral β-aryl- or β-hetaryl-α-N-benzyl/N-acetyl/N-Boc substituted α- aminomethylacrylates used as substrates were prepared by a Baylis-Hillman react
Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones
Peukert, Stefan,Sun, Yingchuan,Zhang, Rui,Hurley, Brian,Sabio, Mike,Shen, Xiaoyu,Gray, Christen,Dzink-Fox, JoAnn,Tao, Jianshi,Cebula, Regina,Wattanasin, Sompong
, p. 1840 - 1844 (2008/09/19)
Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one-3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. S
Asymmetric synthesis of β2-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives
Beddow, James E.,Davies, Stephen G.,Ling, Kenneth B.,Roberts, Paul M.,Russell, Angela J.,Smith, Andrew D.,Thomson, James E.
, p. 2812 - 2825 (2008/03/12)
Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4- isopropyl-5,5-dimethyloxazolidin-2-one (derived from l-valine) and alkylation of the resultant lithium β-amino enolate provides, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yield and high ee. Alternatively, via a complementary pathway, conjugate addition of a range of secondary lithium amides to (S)-N(3)-(2′-alkylacryloyl)-4-isopropyl-5,5- dimethyloxazolidin-2-ones, diastereoselective protonation with 2-pyridone, and subsequent deprotection furnishes a range of (R)-2-alkyl- and (R)-2-aryl-3-aminopropanoic acids in good yield and high ee. Additionally, the boron-mediated aldol reaction of β-amino N-acyl oxazolidinones is a highly diastereoselective method for the synthesis of a range of β-amino- β′-hydroxy N-acyl oxazolidinones. The Royal Society of Chemistry.
Efficient synthesis of β2-amino acid by homologation of α-amino acids involving the reformatsky reaction and Mannich-type imminium electrophile
Moumne, Roba,Lavielle, Solange,Karoyan, Philippe
, p. 3332 - 3334 (2007/10/03)
Development of new methods for the synthesis of β-amino acids is important as polymers of these compounds are promising peptidomimetic candidates in medicinal chemistry. We report here our findings on a new and highly efficient general strategy for the synthesis of β2-amino acids by homologation of α-amino acids, involving the Reformatsky reaction and Mannich-type imminium electrophile.
A New Approach to Enantiomerically Pure β-Lactams from α-Amino Acids by Applying the Isonitrile-Nitrile Rearrangement
Haaf, Klaus,Ruechardt, Christoph
, p. 635 - 638 (2007/10/02)
(S)-Phenylalanine (1) was converted into (S)-3-benzyl-2-azetidinone (8b) by a multistep reaction sequence.The key step of this approach is a stereospecific isonitrile-nitrile rearrangement ( 3 -> 4) by flash pyrolysis, which may be performed in 20-g batch
