A novel conformationally restricted analogue of 3-methylaspartic acid via stereoselective methylation of chiral pyrrolidin-2-ones

Crucianelli, Emanuela; Galeazzi, Roberta; Martelli, Gianluca; Orena, Mario; Rinaldi, Samuele; Sabatino, Piera

doi:10.1016/j.tet.2009.10.004

Cited by 16 publications

(5 citation statements)

References 40 publications

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“…According to the HSQC spectrum and a previous report, proton signals at δ H 6.66 (2H, d, J = 8.1 Hz), 7.23 (2H, d, J = 8.2 Hz), together with their corresponding carbon signals at δ C 114.9 and 131.8, respectively, as well as signals at δ H 6.72 (2H, d, J = 8.0 Hz) and 7.05 (2H, d, J = 8.0 Hz) with their corresponding carbon signals at δ C 115.3 and 127.7, respectively, suggested the presence of two symmetrical para -substituted aromatic protons [20]. Besides, signals at δ H 4.48 (1H, d, J = 7.8 Hz), 3.27 (1H, d, J = 9.9 Hz), and 3.98 (1H, d, J = 9.3 Hz), together with their corresponding carbon signals at δ C 40.33 and 57.0, respectively, and a carbonyl carbon signal at δ C 170.8 revealed a pyrrolidine-2-one ring [21]. Furthermore, the existence of a methyl group at δ H 2.98 (3H, s) was noticeable in the 1 H-NMR spectrum.…”

Section: Resultsmentioning

confidence: 99%

Bioactivities of a New Pyrrolidine Alkaloid from the Root Barks of Orixa japonica

et al. 2016

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Abstract:A new pyrrolidine alkaloid named (Z)-3-(4-hydroxybenzylidene)-4-(4-hydroxyphenyl)-1-methylpyrrolidin-2-one was isolated from the ethanol extract of the root barks of Orixa japonica. The structure of the new alkaloid was elucidated on the basis of NMR and MS analysis. The compound exhibited larvicidal activity against the fourth instar larvae of Aedes aegypti (LC 50 = 232.09 µg/mL), Anopheles sinensis (LC 50 = 49.91 µg/mL), and Culex pipiens pallens (LC 50 = 161.10 µg/mL). The new alkaloid also possessed nematicidal activity against Bursaphelenchus xylophilus (LC 50 = 391.50 µg/mL) and Meloidogynein congnita (LC 50 = 134.51 µg/mL). The results indicate that the crude ethanol extract of O. japonica root barks and its isolated pyrrolidine alkaloid have potential for development into natural larvicides and nematicides.

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Section: Resultsmentioning

confidence: 99%

Bioactivities of a New Pyrrolidine Alkaloid from the Root Barks of Orixa japonica

et al. 2016

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“…The same research group utilized analogous methods to prepare other pyrrolidinone-based β-amino acid stereoisomers as conformationally restricted analogs of aspartic acid and peptidomimetics for the synthesis of novel β-foldamers …”

Section: Cyclic β-Amino Acids With a Heteroatom In The Ringmentioning

confidence: 99%

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

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Introduction 1116 2. Carbocyclic β-Amino Acids 1118 2.1. Syntheses of Five-or Six-Membered Carbocyclic β-Amino Acids 1118 2.1.1. Carbocyclic β-Amino Acids from β-Keto Esters 1119 2.1.2. Carbocyclic β-Amino Acids by Metathesis 1119 2.1.3. Carbocyclic β-Amino Acids by Amino Group Conjugate Addition 1122 2.1.4. Carbocyclic β-Amino Acids by Cycloaddition 1124 2.1.5. Carbocyclic β-Amino Acids by Desymmetrization of meso-Anhydrides 1124 2.1.6. Carbocyclic β-Amino Acids from Natural Sources 1125 2.1.7. Miscellaneous 1127 2.2. Syntheses of Small-Ring Carbocyclic β-Amino Acids 1128 2.3. Syntheses of Carbocyclic β-Amino Acids with Larger Ring Systems 1129 2.4. Synthesis of Functionalized Carbocyclic β-Amino Acids 1131 2.4.1. Syntheses of Functionalized Cyclic β-Amino Acids by C−C Double Bond Functionalization 1131 2.4.2. Several Relevant Routes to Functionalized Cyclic β-Amino Acids Other Than Functionalization of the Ring C−C Double Bond 1137 3. Cyclic β-Amino Acids with a Heteroatom in the Ring 1137 3.1. Syntheses of Cyclic β-Amino Acids with a N Atom in the Ring 1138 3.1.1. Three-and Four-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.2. Five-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.3. Six-Membered N-Containing Cyclic β-Amino Acids 1145 3.1.4. N-Containing Cyclic β-Amino Acids with Larger Ring Systems 1148 3.2. Syntheses of Cyclic β-Amino Acids with an O Atom in the Ring 1148 3.2.1. Four-Membered O-Containing Cyclic β-Amino Acids 1148 3.2.2. Five-Membered O-Containing Cyclic β-Amino Acids 1149 3.2.3. Six-Membered O-Containing Cyclic β-Amino Acids 1155 3.3. Cyclic β-Amino Acids with Other Heteroatoms in the Ring 1159 4. Some Relevant Biological Properties of Cyclic β-Amino Acids 1160 4.1. Cyclic β-Amino Acids Possessing Antifungal or Antibacterial Properties 1160 4.2. Antiviral Cyclic β-Amino Acids 1162 4.3. Cyclic β-Amino Acids with Antitumoral Properties 1162 4.4. Cyclic β-Amino Acids with Cardioprotective

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“…In fact, owing to the easy removal of the 4-methoxyphenylethyl group, the N-1 of the pyrrolidin-2-one ring could be appropriately functionalised with polar chains. Thus, stereoselective alkylation of 5 b led to the corresponding derivative 6 b, the fully protected (3R,4S,1'S)-4-amino-1-(1'-(4-methoxyphenyl)ethyl)-3-methyl-5-oxopyrrolidine-3-carboxylic acid ((3R,4S,1'S)-AMMOPC; 6 a, Scheme 2), [29] and this unit was employed in an attempt to modify the foldamer conformation to intro- duce a quaternary centre in the monomer. Thus, by using standard homogeneous peptide synthesis, starting from 6 b the corresponding hexamer 7 was obtained and its conformation was first assigned by means of NMR analysis and then confirmed by MD simulations.…”

Section: Dedicated To Professor Giuliana Cardillomentioning

confidence: 99%