122442-02-8Relevant articles and documents
Enantioselective Three-Step Synthesis of Homo-β-proline: A Donor-Acceptor Cyclopropane as Key Intermediate
Pilsl, Ludwig K. A.,Ertl, Thomas,Reiser, Oliver
, p. 2754 - 2757 (2017)
An enantioselective three-step synthesis of the GABA uptake inhibitor (S)-(+)-homo-β-proline was developed. The basis for the synthesis was the enantioselective CuI-catalyzed cyclopropanation of N-Boc-pyrrole, a substrate that persistently has proved to be challenging in such transformations. The cyclopropanation can be performed on a 150 mmol scale, and the two subsequent steps (i.e., hydrogenation and in situ cyclopropane-opening/double-deprotection) toward the target molecule proceed smoothly in quantitative yield without loss of enantiopurity.
Piperazine ureido derivative, preparation method thereof and application of piperazine ureido derivative in medicine
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Paragraph 0238; 0240; 0241; 0242; 0243, (2021/05/12)
The invention relates to piperazine ureido derivatives, a preparation method thereof and an application of the piperazine ureido derivatives in medicine. In particular, the invention relates to piperazine ureido derivatives as shown in a general formula (I), a preparation method thereof, pharmaceutical compositions containing the derivatives, and uses thereof as capsid protein inhibitors, especially in prevention and/or treatment of hepatitis B, influenza, herpes, AIDS and other diseases. Wherein the definition of each group in the general formula (I) is the same as that in the specification.
Chiral bicyclic guanidine as a versatile bronsted base catalyst for the enantioselective michael reactions of dithiomalonates and β-keto thioesters
Ye, Weiping,Jiang, Zhiyong,Zhao, Yujun,Goh, Serena Li Min,Leow, Dasheng,Soh, Ying-Teck,Tan, Choon-Hong
, p. 2454 - 2458 (2008/09/19)
A chiral bicyclic guanidine was developed as a versatile Bronsted base catalyst for the enantioselective Michael reactions of dithiomalonates and β-keto thioesters using a range of acceptors including maleimides, cyclic enones, furanone and acyclic 1,4-di
A convenient chemoenzymatic synthesis of (R)-(-) and (S)-(+)-homo-β- proline
Felluga, Fulvia,Gombac, Valentina,Pitacco, Giuliana,Valentin, Ennio
, p. 3323 - 3327 (2007/10/03)
Both enantiomers of the heterocyclic GABA analogue homo-β-proline (3-pyrrolidineacetic acid) were synthesized by a chemoenzymatic method involving the use of two enantiocomplementary enzymes in the disymmetric hydrolyses of 3-nitromethylglutaric acid diethyl ester.
Conformationally constrained no synthase inhibitors: Rigid analogs of L- N-iminoethylornithine
Eustache, Jacques,Grob, Alfred,Lam, Charles,Sellier, Odile,Schulz, Gerhard
, p. 2961 - 2966 (2007/10/03)
The synthesis of eight rigid analogs of L-N-iminoethylomithine (L-NIO) is described. The compounds have been evaluated for their inhibition of inducible nitric oxide synthase. Preliminary structure-activity relationships are discussed.
A practical ex-chiral-pool synthesis of β-proline and homo-β-proline
Thomas, Christoph,Orecher, Florian,Gmeiner, Peter
, p. 1491 - 1496 (2007/10/03)
Starting from aspartic acid an efficient synthesis of enantiomerically pure β-proline and homo-β-proline is described. The key step of the synthesis includes formation of the 1,4-biselectrophile 6, followed by rearrangement via the aziridinium intermediate 7 and ring closure to give the pyrrolidinium salt 9a which can serve as a common precursor for both target compounds.
Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid
Galeazzi, Roberta,Geremia, Silvano,Mobbili, Giovanna,Orena, Mario
, p. 79 - 88 (2007/10/03)
By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers wa
A convenient approach to diastereomerically pure 1,3,4-trisubstituted pyrrolidin-2-ones by intramolecular cyclisation of N-(2-alken-1-yl)amides mediated by Mn(III). An entry to both (R)- and (S)-3-pyrrolidineacetic acid
Galeazzi, Roberta,Mobbili, Giovanna,Orena, Mario
, p. 1069 - 1084 (2007/10/03)
The oxidative cyclisation of a series of either (S)-N-(2-alken-1-yl)-N-(1-phenyleth-1-yl)-acetoacetamides 5a-d and methoxycarbonylacetamides 6a-b, performed by using Mn(OAc)3 · 2H2O and Cu(OAc)2 · H2O in acetic
GABA Agonists and Uptake Inhibitors. Synthesis, Absolute Stereochemistry, and Enantioselectivity of (R)-(-)- and (S)-(+)-Homo-β-proline
Nielsen, Lone,Brehm, Lotte,Krogsgaard-Larsen, Povl
, p. 71 - 77 (2007/10/02)
The cyclic analogue of 4-aminobutyric acid (GABA), 3-pyrrolidineacetic acid (homo-β-proline), is a potent agonist at GABAA receptors, it interacts effectively with GABA-uptake mechanisms, and it is a moderately potent inhibitor of GABAB/s