29588-88-3Relevant academic research and scientific papers
Synthesis of new amides based on N-Phthaloyl-α-Amino Acids
Tukhtaev,Yusupov,Vinogradova
, p. 3049 - 3058 (2021/05/28)
N-phthaloyl derivatives of aliphatic α-amino acids were synthesized using phthalanhydride under standard conditions. The optimization reaction carried out by the thermal method to obtain the amides of these N-phthaloyl amino acids resulted in transimitted rather than amidation. The target amides of N-phthaloyl-α-amino acids were obtained by acylation of the amine with the corresponding acid chloroanhydrides in dichloromethane. These results were compared with the results of a similar acylation in a non-polar solvent (benzene). The dependence of the direction of the reaction on the duration of the acylation and the amount of amine used was established. The conditions for the formation of the corresponding N-phthaloyl-α-amino acid amides and asymmetric phthalic acid diamides were found. It is noteworthy that the formation of diamides is directly proportional to the equivalent amount of amine and the duration of the reaction, which makes it possible to purposefully control the synthesis in one reactor.
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.
Chiral sensors for determining the absolute configurations of α-amino acid derivatives
Chen, Zhongxiang,Fan, Hongjun,Yang, Shiwei,Bian, Guangling,Song, Ling
, p. 6933 - 6939 (2018/10/02)
A simple strategy for configurational assignments of alpha-amino acids has been developed by comparison of the proton NMR chemical shift values of the alpha hydrogens of N-phthaloyl protected alpha-amino acids in the presence of (R)-CSA 1 and (S)-CSA 1, respectively. Highly resolved NMR spectra can be obtained directly on the mixed solution of the chiral solvating agents with N-phthaloyl protected alpha-amino acids in NMR tubes, giving well distinguishable proton signals without interference which dramatically improve the accuracy of assignment and hasten the assigning procedure. The strategy is widely applicable for varied natural and non-natural amino acids.
Chelation-Assisted Palladium-Catalyzed γ-Arylation of Aliphatic Carboxylic Acid Derivatives
Dey, Aniruddha,Pimparkar, Sandeep,Deb, Arghya,Guin, Srimanta,Maiti, Debabrata
supporting information, p. 1301 - 1307 (2017/04/18)
A palladium(II)-catalyzed protocol for the highly regioselective remote γ-C–H arylation of aliphatic carboxylic acid has been disclosed. The 8-aminoquinoline moiety as an intramolecular bidentate chelator was found to be suitable for this γ-C–H arylation. Various aryl iodides successfully produced the regioselectively mono-arylated products with negligible diarylation. Functional group tolerance and easy-to-handle reaction conditions make this method attractive. (Figure presented.).
Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary
Vincent, Adrien,Deschamps, Damien,Martzel, Thomas,Lohier, Jean-Fran?ois,Richards, Christopher J.,Gaumont, Annie-Claude,Perrio, Stéphane
, p. 3961 - 3966 (2016/05/24)
Acyl chloride of N-phthaloyl-(S)-isoleucine is an efficient chiral auxiliary for the resolution of (±)-[2.2]paracyclophane-4-thiol. A preparative protocol, based on the conversion into diastereoisomeric thiolesters and separation by two fractional crystallizations and column chromatography, was developed. Deprotection with LiAlH4 allowed isolation of the individual thiol enantiomers in good yield (～40%) and high enantiomeric purity (ee >93%). The absolute configurations were determined by comparison of the optical rotation value of the products with literature data and were confirmed by X-ray crystallography.
Phthaloyl amino acids as anti-inflammatory and immunomodulatory prototypes
Leite, Ana Cristina Lima,Barbosa, Fabio Fernandes,Cardoso, Marcos Verissimo De Oliveira,Moreira, Diogo R. M.,Coelho, Lucas Cunha D.,Da Silva, Elany Barbosa,Filho, Gevanio Bezerra De Oliveira,De Souza, Valdenia Maria Oliveira,Pereira, Valeria Rego A.,Reis, Luiza De C.,Ferreira, Paulo Michel Pinheiro,Pessoa, Claudia,Wanderley, Almir Goncalves,Mota, Fernanda Virginia B.,Da Silva, Teresinha G.
, p. 1701 - 1708 (2014/05/06)
A series of phthalimide analogs were synthesized by derivatization of phthalic anhydride, a highly toxic substance, using a "one pot" condensation reaction to α-amino acids. All phthaloyl amino acid derivatives presented anti-oral inflammatory activity, but compounds 2e and 2g were found to possess the best activities comparable to thalidomide.Most of the compounds effectively suppressed nitric oxide production inmurine cells stimulatedwith lipopolysaccharide. N-phthaloyl amino acids did not exhibit any significant cytotoxicity in vitro when tested against tumor cells as well as a spleen cell culture of BALB/c mice. Compounds 2a, 2g, and 2h were able to inhibit TNF-α and IL-1β production by macrophages. At the same concentration, thalidomide did not exhibit significant inhibitory activity. Springer Science+Business Media 2013.
Unexpected stereoselective synthesis of (Z)-β-alkenyl substituted β-amino phosphonates through β,γ-dihydrogen shift reaction catalyzed by a copper(I) complex and iodine [Cu(MeCN)4]PF 6/I2
Cai, Yan,Lyu, Hairong,Yu, Chengbin,Miao, Zhiwei
supporting information, p. 596 - 602 (2014/05/20)
A series of dialkyl a-diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN) 4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl a-diazophosphonates gave a mixture of β,γ-dihydrogen shift and 1,2-hydride migration products and afforded β-alk- enyl-substituted β-amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.
Novel phthalimide derivatives with TNF-α and IL-1β expression inhibitory and apoptotic inducing properties
Coêlho, Lucas Cunha Duarte,De Oliveira Cardoso, Marcos Veríssimo,Moreira, Diogo Rodrigo Magalh?es,De Moraes Gomes, Paulo André Teixeira,Cavalcanti, Suellen Melo Tibúrcio,Oliveira, Arsenio Rodrigues,De Oliveira Filho, Gevanio Bezerra,Pessoa De Siqueira, Lucianna Rabelo,De Oliveira Barbosa, Miria,De Oliveira Borba, Elizabeth Fernanda,Da Silva, Teresinha Gon?alves,Kaskow, Belinda,Karimi, Mahdad,Abraham, Lawrence J.,Leite, Ana Cristina Lima
, p. 758 - 765 (2014/06/10)
Modulation of the immune system is an emerging concept in the control of tumor growth. Bearing in mind the pharmacological properties of thalidomide and its phthalimide derivatives, we describe here the structural design, synthesis and pharmacological evaluation of N-acylhydrazones derived from phthalimide. The ability of these N-acylhydrazones in inhibiting the secretion of TNF-α in stimulated cells as well as in inhibiting the transcription of the TNF-α gene was evaluated. We identified N-acylhydrazones 6b and 9c, which substantially impaired TNF-α secretion, expression and reduced IL-1β production similar to thalidomide or Revlimid. N-Acylhydrazone 9c was also able to induce apoptosis in Jurkat cells, however it does not have either antiproliferative properties or cytotoxicity for mouse splenocytes. Beyond that, we have assayed the ability of these compounds to induce cell death and a number of them are able to induce apoptosis.
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.
Diastereoselective synthesis of γ-phthalimido-β-hydroxy esters and n-protected 4-amino-1,3-diols starting from natural α-amino acids
Essersi, Amel,Touati, Ridha,Hassine, Bechir Ben
scheme or table, p. 69 - 72 (2010/08/05)
An efficient diastereoselective synthes.is of γ-phthalimido-β- hydroxy esters and N-protected 4-amino-1,3- diols, starting from natural amino acids is described. The key synthetic strategies involve diastereoselective reduction of γ-phthalimido-β-keto esters with NaBH4 as hydride reducing. The diastereoselective reduction has been found to be highly selective if carried out in methanol at -78°C. Furthermore, the resulting diastereomeric mixture of the reduced products was successfully and cleanly separated by column chromatography.
