- Synthesis and biological evaluation of new curcumin analogs inhibiting osteoclastogenesis
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A series of curcumin analogs (1-3) were newly designed and synthesized for the development of therapeutic agents for osteoporosis. Among the synthesized compounds, 2,5-substituted conjugated thiophene derivative (1a) and the corresponding pyrazine derivat
- Kawano, Tomikazu,Matsumoto, Naomi,Nakanishi-Matsui, Mayumi,Ogawa, Satoshi,Ohashi, Toshika,Sugawara, Aoi,Tamura, Satoru
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p. 1233 - 1247
(2020/09/18)
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- Synthesis and characterization of Co(II) and Mn(II) [M3L3] triangles
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Abstract: We report an improved method to make the ligand N,N′-(pyrazine-2,5-diylbis(methanylylidene))bis(2-(pyridin-2-yl)ethanamine) (L) and the subsequent complexation of this ligand to make the triangular metallo-macrocycles [Co3L3/sub
- Dais, Tyson N.,Brown, Michael J.,Coles, Martyn P.,Laur, Fran?ois,Price, Jason R.,Rowlands, Gareth J.,Plieger, Paul G.
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p. 175 - 182
(2019/07/16)
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- Self-Assembly of Cyclohelicate [M3L3] Triangles Over [M4L4] Squares, Despite Near-Linear Bis-terdentate L and Octahedral M
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Self-assembly of 1:1:2 MII(BF4)2 (M=Zn or Fe), pyrazine-2,5-dicarbaldehyde (1) and 2-(2-aminoethyl)pyridine gave trimetallic triangle architectures rather than the anticipated tetrametallic [2×2] squares. Options for the n
- Hogue, Ross W.,Dhers, Sébastien,Hellyer, Ryan M.,Luo, Jingwei,Hanan, Garry S.,Larsen, David S.,Garden, Anna L.,Brooker, Sally
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p. 14193 - 14199
(2017/10/07)
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- BIS-AMINES, COMPOSITIONS, AND USES RELATED TO CXCR4 INHIBITION
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This disclosure relates bis-amine compounds disclosed herein and uses related to CXCR4 inhibition. In certain embodiments, the compounds have formula (I), salts, derivatives, and prodrugs thereof wherein, A is a bridging aryl or heterocyclyl and R1 and R2 are further disclosed herein. In certain embodiments, the disclosure contemplates pharmaceutical compositions comprising compounds disclosed herein. In certain embodiments, the disclosure relates to methods of treating or preventing CXCR4 related diseases or conditions by administering an effective amount of a compound disclosed herein to a subject in need thereof.
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- Pyrazine-fused isoindigo: A new building block for polymer solar cells with high open circuit voltage
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Pyrazine-fused isoindigo (PzIIG) was designed and synthesized as a novel electron acceptor to construct two D-A conjugated polymers, PzIIG-BDT2TC8 and PzIIG-BTT2TC10. Both the polymers were successfully applied in polymer solar cells, and the PzIIG-BDT2TC8 based solar cell device exhibited a PCE of 5.26% with a high Voc over 1.0 V.
- Li, Jiu-Long,Chai, Yun-Fei,Wang, Wei Vanessa,Shi, Zi-Fa,Xu, Zhu-Guo,Zhang, Hao-Li
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p. 5882 - 5885
(2017/07/11)
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- NITROGEN-CONTAINING HETEROCYCLIC ALKENYL COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL AND ORGANIC SEMICONDUCTOR DEVICE
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PROBLEM TO BE SOLVED: To provide a compound that is high in charge transfer and atmosphere stability and is suitable for an organic semiconductor material, provide an organic semiconductor material comprising the compound, and provide an organic semiconductor element comprising the organic semiconductor material. SOLUTION: The present invention provides a compound represented by formula (1), specifically a compound represented by formula (2) (Ar1 is an unsaturated cyclic hydrocarbon group or the like; Ar2 is an unsaturated heterocyclic group containing nitrogen with an unshared electron pair, or the like; B is -CH=CH- or -C≡C-; X11-X13 independently represent C-R or N; at least one of X12 and X13 is N). SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2018,JPOandINPIT
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- Regioselective double Boekelheide reaction: First synthesis of 3,6-dialkylpyrazine-2,5-dicarboxaldehydes from dl-alanine
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Pyrazine-2,5-dicarboxaldehyde was synthesized on a multi-gram scale by MnO2 oxidation of 2,5-bis(hydroxymethyl)pyrazine, which in turn was obtained from 2,5-dimethylpyrazine employing double Boekelheide reaction as a key step as reported previously. This reaction was subsequently utilized in a regioselective fashion as a key step to synthesize efficiently, for the first time, 3,6-di(long-chain)alkylpyrazine-2,5-dicarboxaldehydes starting from dl-alanine. These monomers are certain to have importance as electron deficient and chemically versatile components for new materials development.
- Das, Sajal Kumar,Frey, Joseph
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p. 3869 - 3872
(2012/08/14)
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- RuII multinuclear metallosupramolecular rack-type architectures of polytopic hydrazone-based ligands: Synthesis, structural features, absorption spectra, redox behavior, and near-infrared luminescence
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A novel class of polytopic hydrazone-based ligands was synthesized. They gave heteroleptic RuII polynuclear rack-like complexes of formula [Runterpyn molecular strand)]2n+ (terpy = 2,2′:6′,2″-terpyridine). The new rack-like systems can be viewed as being made of two identical or roughly identical peripheral subunits separated by several similar metal-containing spacer subunits. The presence of pyrazine or pyrimidine units within the molecular multitopic strands introduces additional chemical diversity; whereas a pyrimidine unit leads to appended orthogonal subunits that are on the same side with regard to the main molecular strand, a pyrazine unit leads to orthogonal subunits that lie on different sides. Mixing pyrazine and pyrimidine units within the same (bridging) molecular strand also allows peculiar and topographically controlled geometries to be obtained. Redox studies provided evidence that each species undergoes reversible redox processes at mild potentials, which can be assigned to specific subunits of the multicomponent arrays. Non-negligible electronic coupling takes place among the various subunits, and some electron derealization ex-tending over the overall bridging molecular strand takes place. In particular, oxidation data suggest that the systems can behave as p-type "molecular wires" and reduction data indicate that n-type electron conduction can occur within the multimetallic framework. All the multinuclear racks exhibit 3MLCT emission, both at 77 K in rigid matrix and at 298 K in fluid solution, which takes place in the near-infrared region (emission maxima in the 1000-1100 nm region), and is quite structured. Rigidity of the molecular structures and derealization within the large bridging ligands are proposed to contribute to the occurrence of the rather uncommon MLCT infrared emission, which is potentially interesting for optical communication devices.
- Stadler, Adrian-Mihail,Puntoriero, Fausto,Nastasi, Francesco,Campagna, Sebastiano,Lehn, Jean-Marie
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body text
p. 5645 - 5660
(2010/07/16)
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- Control of relative direction and amplitude in extension/contraction motions of molecular strands induced by ion binding
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The shape of ligand strands composed of six-membered aza-heterocycles (het) connected at the a and α' positions by hydrazone (hyz) units is determined in a predictable fashion by the nature of the heterocyclic groups (pyridine, pyrimidine, pyrazine etc.), and covers the range from extended linear to compact helical structures. The binding of metal ions to the coordination subunits, defined by the hethyz sequences, leads to marked shape changes by inter-converting bent and linear conformations of the subunits, thus inducing relative motions of strand domains either in the same (con-sense, "twirling") or in opposite (dis-sense, "flapping") directions. The amplitude of the motion induced by metal-ion binding and release and the relative directions of the formal motions can be controlled by the nature of the heterocyclic units. Thus, motions around a central 4,6-disubstituted pyrimidine are dis-sense motions, whereas there are con-sense motions around a central 2,5-disubstituted pyrazine unit, as illustrated by model ligands 1 and 2, respectively. The more extended helical 3 and undulating (zigzag shape) 4 ligands undergo larger-amplitude motions combining the relative displacements displayed by 1 and 2. Ligands 3 and 4 form linear tetranuclear PbII and Zn" complexes, thus producing an extension motion. The same holds for [Ru(4)(terpy)4](PF6)8 (terpy = terpyridine). Reversible acid-base-triggered molecular motions have been generated with [Zn4;)(OTf)8] (TfOH = triflic acid
- Stadler, Adrian-Mihail,Ramirez, Juan,Lehn, Jean-Marie
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scheme or table
p. 5369 - 5378
(2010/09/15)
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- Synthesis, structural features, absorption spectra, redox behaviour and luminescence Properties of ruthenium(II) rack-type dinuclear complexes with ditopic, hydrazone-based ligands
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The isomeric bis(tridentate) hydrazone ligand strands 1a-c react with [Ru(terpy)Cl3] (terpy = 2,2':6'.2"-terpyridine) to give dinuclear rack-type compounds 2a-c, which were characterised by several techniques, including X-ray crystallography and NMR methods. The absorption spectra, redox behaviour and luminescence properties (both in fluid solution at room temperature and in rigid matrix at 77 K) of the ligand strands 1a-c and of the metal complexes 2a-c have been studied. Compounds 1a-c exhibit absorption spectra dominated by intense π-π* bands, which, in the case of 1b and 1c, extend within the visible region, while the absorption spectra of the rack-type complexes 2a-c show intense bands both the in the UV region, due to spin-allowed ligand-centred (LC) transitions, and in the visible, due to spin-allowed metal-to-ligand charge-transfer (MLCT) transitions. The energy position of these bands strongly depends on the ligand strand: in the case of 2a. the lowest energy MLCT band is around 470 nm, while in 2b and 2c, it lies beyond 600 nm. Ligands 1a-c undergo oxidation processes that involve orbitals based mainly on the CH3-N-N= fragments. The complexes 2a-c undergo reversible metal-centred oxidalion, while reductions involve the hydrazone-based ligands: in 2b and 2c, the bridging ligand is reduced twice and in 2a once before reduction of the peripheral terpy ligands takes place. Ligands 1a-c exhibit luminescence from the lowest-lying 1π-π* level. Only for complex 2a does emission occur; this may be attributed to a 3MLCT state involving the bridging ligand. Taken together, the results clearly indicate that the structural variations introduced translate into interesting differences in the spectroscopic, luminescence and redox properties of the ligand strands as well as of the rack-type metal complexes.
- Stadler, Adrian-Mihail,Puntoriero, Fausto,Campagna, Sebastiano,Kyritsakas, Nathalie,Welter, Richard,Lehn, Jean-Marie
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p. 3997 - 4009
(2007/10/03)
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- OXIDATION OF 2,5-DIMETHYLPYRAZINE WITH OXYGEN IN THE VAPOR PHASE ON OXIDE CATALYSTS AND IN THE LIQUID PHASE IN THE PRESENCE OF BASES
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The vapor-phase oxidation of 2,5-dimethylpyrazine with oxygen on vanadium-molybdenum oxide catalysts modified with silver oxide gives 5-methyl-2-formylpyrazine and 2,5-diformylpyrazine in 37percent and 35percent yields, respectively.Pyrazine-2,5-dicarboxylic acid was obtained in 53percent yield by the liquid-phase oxidation of 2,5-dimethylpyrazine with oxygen in the presence of a strong base and an interphase catalyst.
- Iovel', I. G.,Yansone, I. Ya.,Gol'dberg, Yu. Sh.,Shimanskaya, M. V.
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p. 456 - 461
(2007/10/02)
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- SYNTHESIS AND CATALYTIC OXIDATION OF 2,5-DIMETHYLPYRAZINE
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The classical method for obtaining 2,5-dimethylpyrazine by cyclization of aminoacetone has been improved by use of ammonium persulfate in place of mercuric chloride in the stage of catalytic oxidation of 2,5-dimethyldihydropyrazine.Catalytic vapor phase oxidation of 2,5-dimethylpyrazine gave 5-methylpyrazine-2-aldehyde and pyrazine-2,5-dialdehyde.
- Kastron, V.V.,Iovel', I.G.,Skrastyn'sh, I.P.,Gol'dberg, Yu.Sh.,Shimanskaya, M.V.,Dubur, G.Ya.
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p. 915 - 917
(2007/10/02)
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