- Synthesis, molecular modeling and biological evaluations of novel pyrrolidine derivatives as potential cyclooxygenase-2 (COX-2) inhibitors
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Abstract: Toward the development of selective cyclooxygenase-2 inhibitors, a series of pyrrolidine derivatives is described. All the compounds containing sulfonamide, ester, nitrile, acid, amide and urea functionalities were computationally screened, and
- Chavan, Kamlesh H.,Kedar, Nathrao Ankushrao,Kanhed, Ashish M.,Agrahari, Vishal Kumar,Sinha, Anshuman
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Read Online
- Nazumazoles A-C, cyclic pentapeptides dimerized through a disulfide bond from the marine sponge theonella swinhoei
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A mixture of nazumazoles A-C (1-3) was purified from the extract of the marine sponge Theonella swinhoei. The mixture was eluted as an extraordinarily broad peak in the reversed-phase HPLC. The structures of nazumazoles were determined by interpretation o
- Fukuhara, Kazuya,Takada, Kentaro,Okada, Shigeru,Matsunaga, Shigeki
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supporting information
p. 2646 - 2648
(2015/06/16)
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- Synthesis and biological evaluation of selective and potent cyclin-dependent kinase inhibitors
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A new series of 2,6,9-trisubstituted purines, structurally related to the cyclin-dependent kinase (CDK) inhibitor Roscovitine, has been synthesized. These compounds mainly differ by the substituent on the C-2 position which encompasses a diol group. These
- N'Gompaza-Diarra, Joannah,Bettayeb, Karima,Gresh, Nohad,Meijer, Laurent,Oumata, Nassima
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p. 210 - 216
(2013/01/15)
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- Synthesis of enantiopure substituted piperidines via an aziridinium ring expansion
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Herein we report a novel methodology for the asymmetric synthesis of 3-substituted piperidines from readily available chiral building blocks. This method, which features a novel irreversible dihydropyrole-tetrahydropyridine ring expansion, allows the intr
- Jarvis, Scott B. D.,Charette, Andre B.
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supporting information; experimental part
p. 3830 - 3833
(2011/09/16)
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- Total synthesis of (+)-dibromophakellin and (+)-dibromophakellstatin
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A new method for the preparation of quaternary chiral aminals has been developed that employs an enamide-type Overman rearrangement process. This methodology was applied to enantioselective total syntheses of (+)-dibromophakellin and (+)-dibromophakellstatin.
- Imaoka, Takuya,Akimoto, Takafumi,Iwamoto, Osamu,Nagasawa, Kazuo
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scheme or table
p. 1810 - 1816
(2011/04/16)
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- Evidence for a stereoelectronic effect in human oxygen sensing
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How PHDs achieve specificity: trans-4-prolyl hydroxylation of the transcription factor HIF occurs with stereochemical retention. Substrate-analogue studies show how the von Hippel Lindau tumor suppressor protein (pVHL) and the oxygen-sensing hydroxylases (PHDs) achieve specificity for hydroxy prolyl/prolyl residues for the C4-exo/endo prolyl conformations, respectively.
- Loenarz, Christoph,Mecinovic, Jasmin,Chowdhury, Rasheduzzaman,McNeill, Luke A.,Flashman, Emily,Schofield, Christopher J.
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scheme or table
p. 1784 - 1787
(2009/09/07)
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- Chiral azabicyclo-N-oxyls mediated enantioselective electrooxidation of sec-alcohols
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Enantiomerically pure azabicyclo-N-oxyls were prepared from l-hydroxyproline. They mediated enantioselective electrooxidation of racemic sec-alcohols to afford optically active sec-alcohols with moderate to high s value (up to 21).
- Shiigi, Hirofumi,Mori, Hiroyuki,Tanaka, Tomoaki,Demizu, Yosuke,Onomura, Osamu
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p. 5247 - 5251
(2008/12/22)
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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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- The first asymmetric synthesis of (2S,3S,4R)-3-amino-2-hydroxymethyl-4- hydroxypyrrolidine
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The novel (2S,3S,4R)-3-amino-2-hydroxymethyl-4-hydroxypyrrolidine 5 has been produced in an efficient synthesis from trans-4-hydroxy-l-proline 8. The key step involves a tethered aminohydroxylation of the alkene 7 to introduce regio- and stereoselectively
- Curtis, Kim L.,Fawcett, John,Handa, Sandeep
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p. 5297 - 5300
(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 42
(2010/02/15)
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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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- Stereospecific coordination of L-hydroxyproline esters with triosmium clusters
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The reactions of cluster (μ-H)Os3(CO)10(μ-OH) with ethyl and isopropyl esters of L-oxyproline were studied.In the presence of Me3NO intermediate complex (μ-H)Os3(CO)9(μ-OH)L (L - isopropyl ester of L-oxyproline) is formed, which slowly converts to the more stable cluster .Cluster complexes containing chelate-bridging heterocycles were also obtained by heating (μ-H)Os3(CO)10(μ-OH) with esters of L-oxyproline.In both cases, only one of the possible diastereomeric complexes (R = Et, Pri) is formed, which indicates that the reactions are stereospecific.Based on analysis of Dreiding's models, an attempt to determine the absolute configuration of the obtained clusters was made. - Keywords: triosmium clusters, L-hydroxyproline esters, stereospecific coordination
- Maksakov, V. A.,Kirin, V. P.,Golovin, A. V.
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p. 1941 - 1945
(2007/10/03)
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- Asymmetric Hydrogenation of Prochiral Olefins Catalyzed by Rhodium Complexes with Chiral Pyrrolidinodiphosphines. Crucial Factors for the Effective Asymmetric Induction
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Remarkable effects of hydrogen pressure on the stereoselectivity were observed in the asymmetric hydrogenations of itaconic acid, α-(acylamino)acrylic acid, and their derivatives catalyzed by rhodium complexes of chiral pyrrolidinodiphosphines.Effects of added triethylamine on the pressure dependency of stereoselectivity were also studied.Marked differences in the direction of asymmetric induction were found in the asymmetric hydrogenations of the methylsuccinic acid precursors itaconic acid, citraconic acid, and mesaconic acid.This result clearly indicates that the chiral recognition by the rhodium catalyst is extremely sensitive to the stereochemistry of the prochiral olefins.Possible mechanisms are discussed on the basis of these results. 31PNMR studies on the key intermediates in asymmetric hydrogenations have revealed that the mode of the bidentate complexation of the prochiral substrates is extremely regioselective.The "induced-fit" phenomena of the chiral rhodium complex were observed.A possible mechanism for the chiral recognition of enantiofaces in the chiral coordination sphere is proposed.
- Ojima, Iwao,Kogure, Tetsuo,Yoda, Noriko
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p. 4728 - 4739
(2007/10/02)
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