Β-aminopropionic Acid Research Articles

Synergistic integration of dihydro-artemisinin with γ-aminobutyric acid results in a more potential anti-depressant

Three hybrids of dihydro-artemisinin (DHA) with β-aminopropionic acid, γ-aminobutyric acid, and histamine have been designed and synthesized. The conjugate of DHA with GABA labelled as 5b was confirmed the most active candidate against both Cort- and SNP-induced PC12 cell impairments with EC50 value of 8.04 ± 0.35, and 9.38 ± 0.56 μM, respectively. 5b was clearly highlighted as a good modulator on protein expression of Akt, Bcl-2, and Bax, indicating its functions against programmed cell apoptosis. 5b significantly reversed the Cort-induced excessive calcium influx and release from internal organelles. It was demonstrated the ability to express increased levels of β-tubulin III and to up-regulate phosphorylation level of cAMP response element-binding protein (CREB), leading to cell differentiation. It can penetrate blood − brain barrier (BBB) with propriate stability. Altogether, these data strongly support that 5b is a potential anti-depressant.

Copper and palladium complexes with substituted pyrimidine-2-thiones and 2-thiouracils: syntheses, spectral characterization, and X-ray crystallographic study

Copper(I) and palladium(II) complexes containing 5-acetyl-6-methyl-1,2,3,4-tetrahydropyrimidine-2-thione (L1), ethyl 4,6-dimethyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (L2), cis-5-acetyl-6-ethyl-5,6-dihydro-2-thiouracil (L3), and 5,6-dihydro-2-thiouracil (L4) have been synthesized. All complexes were characterized by elemental analysis, IR, 1H, and 13C NMR spectroscopy. To assign bands in the IR spectra of L1 and L2 and complexes with Cu(I) and Pd(II), deuterium substitution of movable protons at N-atoms was used. The crystal structures of two compounds, [Cu(L2)2Cl] and [Pd(L4)2Cl2], were determined by X-ray single-crystal and powder diffraction, respectively. In [Cu(L2)2Cl], copper has a rare coordination number of three and triangular surrounding of two neutral L2 molecules, coordinated through sulfurs, and chloride. In [Pd(L4)2Cl2], palladium has a standard square-planar geometry, formed by two uracil molecules and two chlorides. A new method for the synthesis of 5,6-dihydro-2-thiouracil, starting from β-aminopropionic acid, was suggested.

Triangular prism-shaped β-peptoid helices as unique biomimetic scaffolds

β-Peptoids are peptidomimetics based on N-alkylated β-aminopropionic acid residues (or N-alkyl-β-alanines). This type of peptide mimic has previously been incorporated in biologically active ligands and has been hypothesized to be able to exhibit foldamer properties. Here we show, for the first time, that β-peptoids can be tuned to fold into stable helical structures. We provide high-resolution X-ray crystal structures of homomeric β-peptoid hexamers, which reveal right-handed helical conformations with exactly three residues per turn and a helical pitch of 9.6–9.8 Å between turns. The presence of folded conformations in solution is supported by circular dichroism spectroscopy showing length- and solvent dependency, and molecular dynamics simulations provide further support for a stabilized helical secondary structure in organic solvent. We thus outline a framework for future design of novel biomimetics that display functional groups with high accuracy in three dimensions, which has potential for development of new functional materials.

Pt(II) and Pd(II) Complexes with β‐Alanine

A sequence of stages in the syntheses of isomeric bisamino acid complexes of Pt(II) with β-aminopropionic acid (β-alanine = β-AlaH) has been studied by the 195Pt NMR spectroscopy. The techniques have been developed of the synthesis of the cis- and trans-bischelates of Pt(II) and Pd(II) with β-alanine as well as of the halide complexes of trans-[M(β-AlaH)2Cl2] (M = Pt, Pd) and trans-K2[Pt(β-Ala)2I2] types. The NMR spectroscopy and IR spectroscopy (in the nuclei of 195Pt,13C,1H) and X-ray diffraction analysis have been used to examine the structures of the synthesized compounds.

Preparation of both enantiomers of β 2-(3,4-dihydroxybenzyl)-β-alanine, higher homologues of Dopa

β 2-(3,4-Dihydroxybenzyl)-β-alanine [β 2-Homo-Dopa, 1 ] is a novel β-amino acid homologue of Dopa, the most successful therapeutic agent in the treatment of Parkinson's disease. Enantioenriched ( R)- 1 and ( S)- 1 were obtained via the diastereoselective alkylation of enantiopure pyrimidinone ( R)- and ( S)- 3 , chiral derivatives of β-alanine, with veratryl iodide. The major diastereomeric products (2 S,5 R)- 4 and (2 R,5 S)- 4 were hydrolyzed with 57% HBr, and the desired β-amino acids were purified by silica gel chromatography. Alternatively, enantioenriched ( R)- and ( S)- 1 were prepared by means of the highly diastereoselective alkylation (3,4-dimethoxybenzyl iodide) of open-chain β-aminopropionic acid derivatives ( R, R, S)- 8 and ( S, S, R)- 8 containing the chiral auxiliary α-phenylethylamine. Finally, nearly enantiopure ( R)- and ( S)- 1 were obtained by resolution of racemic N-benzyloxycarbonyl-2-(3,4-dibenzyloxybenzyl)-3-aminopropionic acid, rac- 12 , with ( R)- or ( S)-α-phenylethylamine, followed by catalytic hydrogenolysis.

Crystal structure of monohydrate and anhydrous β-alaninium tetrafluoroantimonates(III)

Novel complexes of Sb(III) fluorides with cation of β-aminopropionic acid (β-alanine), (NH3(CH2)2COOH)SbF4 ⋅ H2O (I) and (NH3(CH2)2COOH)SbF4 (II), are synthesized and their crystal structures are determined. Crystals I and II are monoclinic with a = 12.1580(5) A, b = 7.4167(4) A, c = 10.1540(5) A, β = 108.222(2)°, Z = 4, space group P21/c for (I) and a = 10.483(1) A, b = 7.5906(8) A, c = 9.4237(9) A, β = 90.548(2)°, Z = 4, space group P21/c for (II). Structures I and II are formed by β-alaninium cations (C3H8NO2)+ and complex anions [SbF4] n − with polymer chain structure. Complex I also contains crystallization water molecules. In the structures of complexes I and II, the β-alaninium cations have different conformation, the torsion angles C(1)C(2)C(3)N in these complexes are 174.5° and 77.0°C, respectively.

Reactions of -aminopropionic acid N"-acylhydrazides with carbonyl compounds

The reactions of β-aminopropionic acid N"-acylhydrazides with aromatic and heterocyclic aldehydes and acetone afford compounds that exist in solutions predominantly as mixtures of 2-substituted 3-acylaminotetrahydropyrimidin-4-ones (ATHP) and tautomeric Schiff"s bases. These compounds in the crystalline state probably have structures of ATHP. The ratio of tautomers depends on the type of substituent in the aromatic ring and solvent. The reactions of 2-aryl-3-benzamidotetrahydropyrimidin-4-ones with carboxylic or sulfonic acid chlorides afford derivatives of 1-acyl- and 1-tosyl-3-benzamidotetrahydropyrimidin-4-ones.

Enantioselective synthesis of β-amino acids. Part 11: Diastereoselective alkylation of chiral derivatives of β-aminopropionic acid containing the α-phenethyl group

Several novel, chiral derivatives of β-aminopropionic acid were studied as potentially useful precursors of enantiopure α-substituted-β-amino acids. In particular, the diastereoselectivity of alkylation of ( R, R)- 2-Li enolate showed substantial stereoinduction by the bis[α-phenylethyl]amide auxiliary, leading to 80% ds in the methylation reaction. No appreciable effect upon diastereoselectivity was observed by the presence of additives (LiCl, HMPA, DMPU) in the reaction. On the other hand, stereoinduction by the α-phenylethylamino group in the methylation of ester enolate ( S)- 3-Li was lower (65% ds) under standard conditions (THF, −78°C) but improved to 81% ds in the presence of 3 equiv. of HMPA as cosolvent. ‘Matched’ and ‘mismatched’ derivatives, ( R, R, S)- 11 and ( R, R, R)- 11, respectively, were methylated via their corresponding lithium enolates. Observed diastereoselectivities generally followed the anticipated tendencies based on double stereoinduction. Thus diastereoselectivity reached 89% ds in the methylation of the matched isomer, ( R, R, S)- 11-Li.

ChemInform Abstract: Stereoselective Alkylation of Chiral Glycine and Chiral β-Aminopropionic Acid Derivatives in the Preparation of Enantiopure α- and β-Amino Acids

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A Convenient Route to β-Amino Propionic Acid Derivatives

A general convenient procedure for the synthesis of β-amino-propionic acid derivatives from Baylis-Hillman adducts is reported.

Preparation of spiroaziridinefluorene, spiroindoxyl-fluorene, and ?-aminopropionic acid ester with a 4-azafluorene fragment

It has been established that the reaction of 9-(p-methoxyphenylimino)fluorene with dichlorocarbene (conditions of phase-transfer catalysis) proceeds in two directions — the formation of spiroaziridinefluorene and of spiroindoxylfluorene, the structure of which has been demonstrated. Opening of the aziridine ring of spiroaziridinefluorene has been accomplished. From the analagous azamethine, 4-aza-fluorene, an ester of N-substituted Β-aminopropionic acid with a 4-azafluorene fragment was obtained by alkylation of its dianion with methyl chloroacetate.

Physico-chemical investigation on the complexes of indium(III) with Mercapto-, Hydroxy-, and Amino-substituted propionic acid

Potentiometric studies have been carried out on the metal complexes of indium(111) with β-mercaptopropionic, β-hydroxypropionic, and β-aminopropionic acid. The Calvin-Bjerrum pH-titration technique, as used by Irving and Rossotti, has been applied to determine the stepwise formation constants of the complexes. The logK values have been computed by alternative methods. Thermodynamic formation constants have been obtained by extrapolation of the values at various ionic concentrations. The values of overall changes in ΔG, ΔH, and ΔS accompanying complex formation have been evaluated at three different temperatures at an ionic strength of 0.lM (NaClO4). The stability constant of the indium(111) complex decreases as the subsituted group changes from SH to OH to NH2.

Notes- N-(β-Picolyl)glycine, N-(β-Picolyl)-β-aminopropionic Acid, and Their Methyl Derivatives

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTNotes- N-(β-Picolyl)glycine, N-(β-Picolyl)-β-aminopropionic Acid, and Their Methyl DerivativesHarvey Wingfield, Jr.Cite this: J. Org. Chem. 1960, 25, 9, 1671–1672Publication Date (Print):September 1, 1960Publication History Published online18 March 2003Published inissue 1 September 1960https://doi.org/10.1021/jo01079a608RIGHTS & PERMISSIONSArticle Views118Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (258 KB) Get e-Alerts Get e-Alerts

Synthesis and characterization of ?-(?-naphthyl)-?-aminoproionic acid and of certain of its derivatives

1. The method of preparing \gb-naphthaldehyde proposed by Sultanov, Rodionov, and Shemyakin, based on the oxidation of \gb-methylnaphthalene with selenium dioxide, has been improved by the use of naphthalene as solvent. The yield of aldehyde rose from 34 to 66\2-67% of theoretical. 2. N-(\gb-Naphthal)-methylamine and methyl \gb-(\gb-naphthyl)-acrylate are described for the first time. 3. The following have been synthesized; \gb-(\gb-naphthyl)-\gb-aminopropionic acid, its methyl ester, its amide, and its benzoyl and acetyl derivatives, the amide and anilide of N-acetyl-\gb-(\gb-naphthyl)-\gb-aminopropionic acid; and N-methyl-\gb-(\gb-naphthyl)-\gb-aminopropionic acid. β-(β-Naphthyl)-β-aminopropionic acid has been prepared by the basic reaction of Rodionov and also by three variants of this method. 4. N-Methyl-\gb-(\gb-naphthyl)-\gb-aminopropionic acid has been prepared by two methods; one of them is new.

The Preparation and Properties of Some β-Aminopropionic Acid Derivatives

The Preparation and Properties of Some β-Aminopropionic Acid Derivatives