150652-96-3Relevant articles and documents
Efficient synthesis of novel glutamate homologues and investigation of their affinity and selectivity profile at ionotropic glutamate receptors
Pinto, Andrea,Tamborini, Lucia,Mastronardi, Federica,Ettari, Roberta,Romano, Diego,Nielsen, Birgitte,De Micheli, Carlo,Conti, Paola
supporting information, p. 1980 - 1982 (2014/04/17)
A convenient synthesis of four new enantiomerically pure acidic amino acids is reported and their affinity at ionotropic glutamate receptors was determined. The new compounds are higher homologues of glutamic acid in which the molecular complexity has bee
Synthesis and self-assembly of NCN-pincer Pd-complex-bound norvalines
Ogata, Kazuki,Sasano, Daisuke,Yokoi, Tomoya,Isozaki, Katsuhiro,Yoshida, Ryota,Takenaka, Toshio,Seike, Hirofumi,Ogawa, Tetsuya,Kurata, Hiroki,Yasuda, Nobuhiro,Takaya, Hikaru,Nakamura, Masaharu
, p. 12356 - 12375 (2013/09/23)
The NCN-pincer Pd-complex-bound norvalines Boc-D/L-[PdCl(dpb)]Nva-OMe (1) were synthesized in multigram quantities. The molecular structure and absolute configuration of 1 were unequivocally determined by single-crystal X-ray structure analysis. The robustness of 1 under acidic/basic conditions provides a wide range of N-/C-terminus convertibility based on the related synthetic transformations. Installation of a variety of functional groups into the N-/C-terminus of 1 was readily carried out through N-Boc- or C-methyl ester deprotection and subsequent condensations with carboxylic acids, R 1COOH, or amines, R2NH2, to give the corresponding N-/C-functionalized norvalines R1-D/L-[PdCl(dpb)]Nva- R2 2-9. The dipeptide bearing two Pd units 10 was successfully synthesized through the condensation of C-free 1 with N-free 1. The robustness of these Pd-bound norvalines was adequately demonstrated by the preservation of the optical purity and Pd unit during the synthetic transformations. The lipophilic Pd-bound norvalines L-2, Boc-L-[PdCl(dpb)]Nva-NH-n-C 11H23, and L-4, n-C4H9CO-L- [PdCl(dpb)]Nva-NH-n-C11H23, self-assembled in aromatic solvents to afford supramolecular gels. The assembled structures in a thermodynamically stable single crystal of L-2 and kinetically stable supramolecular aggregates of L-2 were precisely elucidated by cryo-TEM, WAX, SAXS, UV/Vis, IR analyses, and single-crystal X-ray crystallography. An antiparallel β-sheet-type aggregate consisting of an infinite one-dimensional hydrogen-bonding network of amide groups and π-stacking of PdCl(dpb) moieties was observed in the supramolecular gel fiber of L-2, even though discrete dimers are assembled through hydrogen bonding in the thermodynamically stable single crystal of L-2. The disparate DSC profiles of the single crystal and xerogel of L-2 indicate different thermodynamics of the molecular assembly process. Metalated amino acids: A series of NCN-pincer Pd-complex-bound norvaline derivatives was successfully synthesized without loss of the optical purity and Pd unit. Efficient self-assembly properties of these Pd-norvalines were found to afford well-regulated Pd arrays both in the single crystal and in the supramolecular gel. A solvent-dependent configuration control of the Pd array was corroborated by means of single-crystal X-ray crystallography and cryo-TEM analysis. Copyright
NOVEL COMPOUNDS FOR MODULATION OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORγ GAMMA, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASE
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, (2011/10/03)
The invention provides modulators for the orphan nuclear receptor RORγ and methods for treating RORγ mediated diseases by administrating these novel RORγ modulators to a human or a mammal in need thereof. Specifically, the present invention provides compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof.
Exploring Leishmania major Inositol Phosphorylceramide Synthase (LmjIPCS): Insights into the ceramide binding domain
Mina, John G.,Mosely, Jackie A.,Ali, Hayder Z.,Denny, Paul W.,Steel, Patrick G.
supporting information; experimental part, p. 1823 - 1830 (2011/04/26)
The synthesis of set of ceramide analogues exploring hydrophobicity in the acyl chains and the degree and nature of hydroxylation is described. These have been assayed against the parasitic protozoan enzyme LmjIPCS. These studies showed that whilst the C-3 hydroxyl group was not essential for turnover it provided enhanced affinity. Reflecting the membrane bound nature of the enzyme a long (C13) hydrocarbon ceramide tail was necessary for both high affinity and turnover. Whilst the N-acyl chain also contributed to affinity, analogues lacking the amide linkage functioned as competitive inhibitors in both enzyme and cell-based assays. A model that accounts for this observation is proposed.
SPIRO (PIPERIDINE-4, 2 ' -PYRROLIDINE) -1- (3, 5- TRIFLUOROMETHYL PHENYL) METHYLCARBOXAMIDES AS NK1 TACHIKYNIN RECEPTOR ANTAGONISTS
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Page/Page column 86, (2009/12/05)
Compounds of formula (I) or a pharmaceutically acceptable salt thereof wherein R is hydrogen or C 1-4 alkyl; R1 is hydrogen, C 1-4 alkyl, C(O)OH, C(O)NH2 or (C 1-4 alkylene)R10; R2 and R3 are independently hydrogen, C 1-4 alkyl or R2 together with R3 and together with the carbon atom to which they are attached form a C3-8 cycloalkyl group; R4 is C 1-4 alkyl, C 1-4 alkoxy or halogen; R5 and R7 are independently hydrogen, hydroxy, halogen, C(O)NH2, C(O)OH or (C 1-4 alkylene) R10; R6 and R8 are independently hydrogen or halogen; R9 is hydrogen, (C 1-4 alkylene)R10, C(O)NH2, C(O)OH or R9 together with R form a 6 membered heterocyclic ring optionally containing a further heteroatom selected from oxygen, sulphur or nitrogen; R10 is hydrogen, halogen, hydroxy, C(O)NH2, C(O)NH(C 1-4 alkyl), C(O)N(C 1-4 alkyl)2 or C(O)OH; n is O, 1 or 2. processes for their preparation, to compositions containing them and to their use in the treatment of diseases and conditions for which antagonism of NK1 is beneficial.
Synthesis of a protected enantiomerically pure 2-deoxystreptamine derivative from D-allylglycine
Busscher, Guuske F.,Rutjes, Floris P.J.T.,Van Delft, Floris L.
, p. 3629 - 3632 (2007/10/03)
A diastereoselective synthetic route from D-allylglycine to the enantiopure (protected) 2-deoxystreptamine derivative 14 is presented. Key steps involve two consecutive chain extensions - with crucial stereodirective roles for the amino protective groups, ring closure by olefin metathesis, face selective dihydroxylation, cyclic sulfate formation and finally opening with azide. The resulting 2-deoxystreptamine derivative is ideally protected for the preparation of 4,5- or 4,6-linked aminoglycoside antibiotics.
Catalytic asymmetric phase-transfer reactions using tartrate-derived asymmetric two-center organocatalysts
Ohshima, Takashi,Shibuguchi, Tomoyuki,Fukuta, Yuhei,Shibasaki, Masakatsu
, p. 7743 - 7754 (2007/10/03)
A new highly versatile asymmetric two-center catalyst, tartrate-derived diammonium salt (TaDiAS), was designed and a catalyst library containing more than 70 new two-center catalysts was constructed. A variety of (S,S)- and (R,R)-TaDiAS were easily synthesized from diethyl L- and D-tartrate, respectively, using common and inexpensive reagents under operationally simple reaction conditions. TaDiAS was used in phase-transfer alkylations and Michael additions to afford various optically active α-amino acid equivalents in up to 93% yield. Moreover, dramatic counter anion effects were observed in phase-transfer catalysis (PTC) for the first time, making it possible to further improve reactivity and selectivity. These findings validate the usefulness of three-dimensional fine-tuning of the catalyst (acetal, Ar, and counter anion) for optimization. Recovery and reuse of the catalyst was also possible using simple procedures. The present asymmetric PTC was successfully applied to enantioselective syntheses of serine protease inhibitor aeruginosin 298-A and its analogues.
Ring opening of homochiral bicyclic oxazolidinones: Synthesis of allylglycinol derivatives
Kim, Sung-Gon,Ahn, Kyo Han
, p. 1387 - 1397 (2007/10/03)
(4R,6aS)-2-Oxo-4-phenyl-2,4,5,6a,7-hexahydrooxazolo[3,2-c]oxazole and its 4-methyl analog were synthesized using (R)-phenylglycinol and (S)- alaninol as the chiral source, respectively. The ring opening reaction of the bicyclic oxazolidinones by an allylt
Chiral electrophilic 'glycinal' equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones
Matsunaga, Hirofumi,Ishizuka, Tadao,Kunieda, Takehisa
, p. 1275 - 1294 (2007/10/03)
The thermal reaction of 3-[(1S)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as α-aminoaldehyde templates useful for the synthesis of a wide variety of optically active α-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones.
Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization
Kitagawa, Osamu,Hanano, Tokushi,Kikuchi, Norihiko,Taguchi, Takeo
, p. 2165 - 2168 (2007/10/02)
The α-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl) pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I2 and s-collidine. The chiral iodides 2 thus obtained were converted to the α-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.
