132666-67-2Relevant academic research and scientific papers
A short diastereoselective synthesis of cis-(2S,4S) and cis-(2R,4R)-4-hydroxyprolines
Gajare, Vikas S.,Khobare, Sandip R.,Malavika,Rajana, Nagaraju,Venkateswara Rao,Syam Kumar
, p. 3743 - 3746 (2015/06/08)
A concise synthesis of (2R,4R)-4-hydroxyproline (1) and (2S,4S)-4-hydroxyproline (2) has been developed in enantiomerically pure form from commercially available starting materials with excellent diastereoselectivity. The tightly bound chelation controlled transition state formed during the 5-exo-tet ring closure reaction is assumed to be the origin of high diastereoselectivity.
Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone
Watanabe, Akiko,Kiyota, Naotoshi,Yamasaki, Tetsuo,Tanda, Kazuhiro,Miyagoe, Tatsunori,Sakamoto, Masanori,Otsuka, Masami
, p. 1132 - 1139 (2011/11/05)
Four isomers of the monomer of peptide nucleic acid (PNA) were derived from (2S,4R)-4-hydroxyproline; they had different stereochemistries at the C 2 and C4 positions in the pyrrolidine ring. These different backbone conformations corresponding to four different stereochemistries were realized through a combination of inversions at the C2 and the C4 positions in pyrrolidine ring. The obtained backbone frameworks were reacted with N-benzoyl thymine to give the corresponding PNA monomers. Spectroscopic comparison of the resultant monomers confirmed their stereochemistries.
FUSED PYRAZINE COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES
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Page/Page column 35, (2009/12/05)
Novel[1.2.4]triazolo[1,5-a]pyrazine and imidazo[1,2-a]pyrazine compounds are disclosed that have a formula represented by the following: The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, and others.
ALPHA-UNSUBSTITUTED ARYLMETHYL PIPERAZINE PYRAZOLO[1,5-A] PYRIMIDINE AMIDE DERIVATIVES
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Page/Page column 197, (2008/12/08)
Methods of preventing, treating or delaying the onset of HIV in a subject by administering to the subject novel pharmaceutically active arylmethyl pyrazolo[1,5-α ]pyrimidine amide derivatives, or pharmaceutical compositions containing the same are described. Additionally, compounds of novel pharmaceutically active arylmethyl piperazine pyrazolo[l,5-α]pyrimidine amide derivatives and their use for the manufacture of specific medicaments are described.
Design and synthesis of APTCs (aminopyrrolidinetricarboxylic acids): Identification of a new group III metabotropic glutamate receptor selective agonist
Schann, Stephan,Menet, Christel,Arvault, Paul,Mercier, Geraldine,Frauli, Melanie,Mayer, Stanislas,Hubert, Nadia,Triballeau, Nicolas,Bertrand, Hugues-Olivier,Acher, Francine,Neuville, Pascal
, p. 4856 - 4860 (2007/10/03)
A new family of mGlu receptor orthosteric ligands called APTCs was designed and synthesized using a parallel chemistry approach. Amongst 65 molecules tested on mGlu4, mGlu6 and mGlu8 subtypes, (2S,4S)-4-amino-1-[(E)-3-carboxyacryloyl]pyrrolidine-2,4-dicar
TRANS PYRROLIDINYL DERIVATIVES AND THEIR PHARMACEUTICAL USE
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Page/Page column 41; 42, (2010/02/15)
The present invention relates to the use of trans pyrrolidinyl of the formula (I) or (II) in which: R1, R2or R3 are hydrogen or a carboxy or amino protecting group; R4 to R8 represent hydrogen or an a
Conformationally-restricted analogues of efflux pump inhibitors that potentiate the activity of levofloxacin in Pseudomonas aeruginosa
Renau, Thomas E.,Leger, Roger,Filonova, Lubov,Flamme, Eric M.,Wang, Michael,Yen, Rose,Madsen, Deidre,Griffith, David,Chamberland, Suzanne,Dudley, Michael N.,Lee, Ving J.,Lomovskaya, Olga,Watkins, William J.,Ohta, Toshiharu,Nakayama, Kiyoshi,Ishida, Yohei
, p. 2755 - 2758 (2007/10/03)
Conformational restriction of the ornithine residue of the efflux pump inhibitor D-ornithine-D-homophenylalanine-3-aminoquinoline (MC-02,595, 2) furnished bioisosteric proline derivatives that were less toxic in vivo and as active as the lead in potentiat
Enantioselective synthesis of 4-hydroxy-D-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition
Merino, Pedro,Revuelta, Julia,Tejero, Tomas,Chiacchio, Ugo,Rescifina, Antonio,Piperno, Anna,Romeo, Giovanni
, p. 167 - 172 (2007/10/03)
The 1,3-dipolar cycloaddition of a chiral nitrone derived from glyoxylic acid and protected D-ribosyl hydroxylamine with the acrylamide of Oppolzer's sultam provides a perfectly stereoselective approach to protected (2R,4R)-4-hydroxy-D-pyroglutamic acid.
Synthesis of the four isomers of 4-aminopyrrolidine-2,4-dicarboxylate: Identification of a potent, highly selective, and systemically-active agonist for metabotropic glutamate receptors negatively coupled to adenylate cyclase
Monn, James A.,Valli, Matthew J.,Johnson, Bryan G.,Salhoff, Craig R.,Wright, Rebecca A.,Howe, Trevor,Bond, Ann,Lodge, David,Spangle, Larry A.,Paschal, Jonathan W.,Campbell, Jack B.,Griffey, Kelly,Tizzano, Joseph P.,Schoepp, Darryle D.
, p. 2990 - 3000 (2007/10/03)
The four isomers of 4-aminopyrrolidine-2,4-dicarboxylate (APDC) were prepared and evaluated for their effects at glutamate receptors in vitro. (2R,4R)-APDC (2a), an aza analog of the nonselective mGluR agonist (1S,3R)- 1-aminocyclopentane-1,3-dicarboxylat
Efficient asymmetric hydrogenation of α-amino ketone derivatives. A highly enantioselective synthesis of phenylephrine, levamisole, carnitine and propranolol
Sukuraba,Takahashi,Takeda,Achiwa
, p. 738 - 747 (2007/10/02)
The complexes of pyrrolidine bisphosphine ligands (CPMs) with rhodium (I) were found to be efficient catalysts for asymmetric hydrogenation of α-amino ketone hydrochloride derivatives. Utilizing this methodology, we have developed efficient asymmetric syntheses of the optically active β-amino alcohols, phenylephrine, levamisole, carnitine and propranolol.
