64927-38-4Relevant academic research and scientific papers
Preparation method for pyrrolidine-2-carboxylic acid derivatives
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Paragraph 0138; 0139, (2016/06/09)
The present invention relates to the field of medical synthesis, in particular to a preparation method for pyrrolidine-2-carboxylic acid derivatives. The present invention adopts the following technical solution: providing a compound having a structure of formula (E), wherein R is R1 or R2, R1 is C1-C6 an alkyl, benzyl, p-methoxybenzyl, or p-nitrobenzyl group, and R2 is hydrogen; R3 is a protecting group of the carboxyl group; and P1 is a protecting group on nitrogen.
An enantioselective route to pyrrolidines: Removal of the chiral template from homochiral pyrroloimidazoles
Jones, Raymond C.F.,Howard, Kevin J.,Snaith, John S.,Blake, Alexander J.,Li, Wang-Shei,Steel, Peter J.
experimental part, p. 8925 - 8936 (2011/12/02)
Two-step reductive removal of the chiral template from optically active pyrroloimidazoles, available from 1,3-dipolar cycloaddition of homochiral 4,5-dihydroimidazolium ylides, gives optically active substituted pyrrolidines. Selective manipulation of the substituents affords, e.g., naturally occurring and other optically active proline derivatives, and optically active pyrrolizidines and indolizidines.
Stereospecific synthesis of cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5-piperidinedicarboxylic acid
Arakawa, Yasushi,Yasuda, Mika,Ohnishi, Masafumi,Yoshifuji, Shigeyuki
, p. 255 - 259 (2007/10/03)
Lactams derived from hetero Diels-Alder adducts were stereospecifically converted into cis-2,4-pyrrolidinedicarboxylic acid and cis-2,5- piperidinedicarboxylic acid by ruthenium tetroxide oxidation. Optically active (2S,4S)-(-)-2,4-pyrrolidinedicarboxylic acid and (2R,4R)-(+)-2,4- pyrrolidinedicarboxylic acid were synthesized from (1S,4R)-(+)-2- azabicyclo[2.2.1]hept-5-en-3-one and (1R,4S)-(-)-2-azabicyclo[2.2.1]hept-5- en-3-one, respectively.
Conformationally Defined Neurotransmitter Analogues. Selective Inhibition of Glutamate Uptake by One Pyrrolidine-2,4-dicarboxylate Diastereomer
Bridges, Richard J.,Stanley, Mark S.,Anderson, Michael W.,Cotman, Carl W.,Chamberlin, A. Richard
, p. 717 - 725 (2007/10/02)
In order to determine the conformational requirements for binding of L-glutamate to the proteins involved in the process of neurotransmission, rigid analogues containing an embedded glutamate moiety have been prepared.These "conformer mimics", the pyrrolidine-2,4-dicarboxylates 4, 7, 11, and 14, were synthesized from commercially available trans-4-hydroxy-L-proline and cis-4-hydroxy-D-proline, and then were tested for their ability to inhibit the high-affinity transport of -L-glutamate into synaptosomes and to block the binding of radioligands to the NMDA (N-methyl-D-aspartate), KA (kainate), and QA (quisqualate) glutamate neurotransmitter receptor sites.While none of the four analogues binds effectively to the excitatory receptors, the L-trans-isomer 7 is a potent and selective competitive inhibitor of L-glutamate transport.These results delineate a specific structural/conformational preference for binding to the uptake system that is distinct from that required for binding to the NMDA, KA, and QA receptors.
Synthesis of two cyclic analogs of glutamic acid: cis- and trans-pyrrolidine-2,4-dicarboxylic acids
Trigalo, Franois,Molliex, Christophe,Champion, Brigitte,Azerad, Robert
, p. 3049 - 3050 (2007/10/19)
The tosyl ester 2 of tetraethyl 1-acetamido-4-hydroxybutane- 1,1,3,3-tetracarboxylate gave 4-methylene glutammic acid in 90% yield by refluxing with concentrated HC1. Treatment of 2 with NaOEt, then with refluxing concentrated HC1 gave a 54% yield of cis
