- A short diastereoselective synthesis of cis-(2S,4S) and cis-(2R,4R)-4-hydroxyprolines
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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.
- Gajare, Vikas S.,Khobare, Sandip R.,Malavika,Rajana, Nagaraju,Venkateswara Rao,Syam Kumar
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p. 3743 - 3746
(2015/06/08)
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- Design and stereoselective synthesis of four peptide nucleic acid monomers with cyclic structures in backbone
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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.
- Watanabe, Akiko,Kiyota, Naotoshi,Yamasaki, Tetsuo,Tanda, Kazuhiro,Miyagoe, Tatsunori,Sakamoto, Masanori,Otsuka, Masami
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p. 1132 - 1139
(2011/11/05)
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- FUSED PYRAZINE COMPOUNDS USEFUL FOR THE TREATMENT OF DEGENERATIVE AND INFLAMMATORY DISEASES
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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.
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Page/Page column 35
(2009/12/05)
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- ALPHA-UNSUBSTITUTED ARYLMETHYL PIPERAZINE PYRAZOLO[1,5-A] PYRIMIDINE AMIDE DERIVATIVES
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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.
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Page/Page column 197
(2008/12/08)
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- Design and synthesis of APTCs (aminopyrrolidinetricarboxylic acids): Identification of a new group III metabotropic glutamate receptor selective agonist
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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
- Schann, Stephan,Menet, Christel,Arvault, Paul,Mercier, Geraldine,Frauli, Melanie,Mayer, Stanislas,Hubert, Nadia,Triballeau, Nicolas,Bertrand, Hugues-Olivier,Acher, Francine,Neuville, Pascal
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p. 4856 - 4860
(2007/10/03)
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- TRANS PYRROLIDINYL DERIVATIVES AND THEIR PHARMACEUTICAL USE
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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
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Page/Page column 41; 42
(2010/02/15)
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- Conformationally-restricted analogues of efflux pump inhibitors that potentiate the activity of levofloxacin in Pseudomonas aeruginosa
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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
- 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
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p. 2755 - 2758
(2007/10/03)
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- Enantioselective synthesis of 4-hydroxy-D-pyroglutamic acid derivatives by an asymmetric 1,3-dipolar cycloaddition
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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.
- Merino, Pedro,Revuelta, Julia,Tejero, Tomas,Chiacchio, Ugo,Rescifina, Antonio,Piperno, Anna,Romeo, Giovanni
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p. 167 - 172
(2007/10/03)
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- 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
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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
- 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.
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p. 2990 - 3000
(2007/10/03)
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- Efficient asymmetric hydrogenation of α-amino ketone derivatives. A highly enantioselective synthesis of phenylephrine, levamisole, carnitine and propranolol
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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.
- Sukuraba,Takahashi,Takeda,Achiwa
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p. 738 - 747
(2007/10/02)
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