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Second Harmonic Generation at a Silver Electrode in the Presence of Phthalazine

Second harmonic generation (SHG) and surface-enhanced Raman Scattering (SERS) are used to examine the phthalazine-silver electrode interface over a wide potential range.The SHG signal is found to exhibit hysteresis negative of the potential of zero charge, in contrast to SERS, which shows the exported irreversible degradation of signal.Hysteresis in the second harmonic signal is likely the results of anion-mediated reorientation of phthalazine.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N462 – PubChem

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Elimination Reactions of Hydrazonium Salts: Experimental and Theoretical Evidence for a Large Stereoelectronic Effect of Nitrogen

Elimination of trimethylamine from hydrazonium salts (8, R = Me) is promoted by base (methoxide ion in methanol).The mechanism is characterized as E2 as shown by substituent effects (rho = +2.57), Broensted coefficients, a primary kinetic isotope effect (kH/kD = 2.10), and solvent effects.Variation in the leaving group (8, R = arylmethyl) shows that N-N bond cleavage is less well advanced in the transition state than C-H bond breaking.The elimination to give the nitrile is syn-periplanar and, using the phthalazinium salt 4 as a model for the anti elimination, an anti/syn ratio of ca. 102 is found.The reactions have been modelled using ab initio methods with the transition structures located at the HF/3-21G level and relative energies computed using the MP2/6-31G* method.Using both H2O and NH3 as model bases to induce elimination on +, the calculated energy for anti elimination is lower (in the range 11-13 kcal mol-1) than that for syn elimination.The implications of the results for the ease of formation of nitriles from aldehydes via the hydrazonium salt route are discussed.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N318 – PubChem

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Syntheses, structures, thermal and luminescent properties of cadmium(II) complexes based on quinazoline and phthalazine

Six cadmium(II) compounds [Cd(Qnz)2(SCN)2] n (1), [Cd(Qnz)2(dca)2]n (2), [Cd(Qnz)2(N3)2]}n (3), [Cd 2(mu-SCN-kappa2N:S)2(SCN) 2(Ptz)4(H2O)2] (4), [Cd(Ptz) 2(dca)2]n (5) and [Cd(Ptz)(MeOH)(N 3)2]n (6) were successfully synthesized and characterized by single-crystal diffraction. Additionally, the samples were characterized by powder X-ray diffraction (PXRD), thermal analysis and IR spectroscopy. The fluorescence properties of 1, 2, 3, 5 and 6 were studied in solid state, while emission spectrum of 4 was recorded in methanolic solution. All they were compared with the fluorescence properties of the free ligands. Additionally, the electronic spectrum of 4 was investigated at the TDDFT level employing B3LYP functional in combination with LANL2DZ.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N272 – PubChem

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Anti- Angiogenic therapy: Strategies to develop potent VEGFR-2 tyrosine kinase inhibitors and future prospect

Tumor angiogenesis has always been a major gap for effective cancer therapy. Interruption of aberrant angiogenesis by specific inhibitors targeting receptor tyrosine kinases (RTKS) has been of great interests to medicinal chemists. Among the factors that are involved in tumor angiogenesis, vascular endothelial growth factor receptor-2 (VEGFR-2) is validated as the most closely related factor which can drive angiogenesis through binding with its natural ligand VEGF. The well-validated VEGF-driven VEGFR-2 signaling pathway can stimulate many endothelial responses, including increasing vessel permeability and enhancing endothelial cell proliferation, migration and differentiation. Consequently, circumventing angiogenesis by VEGFR-2 inhibitors represents a promising strategy for counteracting various VEGFR-2-mediated disorders as well as drug resistance. Over the past decades, a considerable number of novel small molecular VEGFR-2 inhibitors have been exploited with diverse chemical scaffolds. Especially, recent frequently launched inhibitors have declared their research values and therapeutic potentials in oncology. Still, the antiangiogenesis based treatment remains an ongoing challenge. In this review, a comprehensive retrospective of newly emerged VEGFR-2 inhibitors have been summarized, with the emphasis on the structure- Activity relationship (SAR) investigation, and also binding patterns of representative inhibitors with biotargets. On the basis of all of this information, varied strategies for developing potent VEGFR-2 inhibitors and the future prospect of the clinical application of antiangiogenic inhibitors are discussed hereby.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N405 – PubChem

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Intersystem Crossing of Radical Pair in Solvent Cage. External Heavy Atom Effect on Dual Photoreactions of Phthalazine

The effects of the temperature, initial concentration, and chemical quenchers on dual photoreactions of phthalazine were investigated.The results give further supporting evidence for a previously proposed reaction mechanism, i.e., phthalazine in the lowest excited singlet and triplet states affords singlet and triplet radical pairs, respectively, in the initial hydrogen abstraction process from 2-propanol.The singlet radical pair gives a reduction product in a solvent cage, whereas the radicals produced in the triplet state escape from the solvent cage, causing dimerization.On the basis of the reaction mechanism of dual photoreactions, external heavy-atom effects on the radical pairs within a solvent cage have been studied.The results indicate that heavy-atom perturbations bring about an enhancement of the intersystem crossing efficiency from the triplet-state radical pair to the singlet one, including a spin inversion of the radical pair in the solvent cage, rather than S1 -> T1 intersystem crossing induced within a single molecule of phthalazine.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N201 – PubChem

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Visible Light-Mediated Direct Decarboxylative C-H Functionalization of Heteroarenes

The direct visible light-mediated C-H alkylation of heteroarenes using aliphatic carboxylic acids is reported. This mild method proceeds at low catalyst loadings (0.5 mol %) and has a high functional group tolerance and a broad substrate scope. Notably, functionalization of (iso)quinoline, pyridine, phthalazine, benzothiazole, and other heterocyclic derivatives with both cyclic and acyclic primary, secondary, and tertiary carboxylic acids as well as amino and fatty acids proceeded under the standard conditions at room temperature. This protocol enables the rapid conversion of abundant feedstock materials into medically relevant “drug-like” moieties.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N160 – PubChem

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Recent advances in development of GPR40 modulators (FFA1/FFAR1): An emerging target for type 2 diabetes

Background: GPR40, an orphan G-protein coupled receptor that is activated by medium and long-chain fatty acids and is highly expressed in pancreatic islets, adipose depots and the gastrointestinal tract are involved in energy source recognition, absorption, storage and/or metabolism. Since its deorphanization in 2003, G-protein-coupled receptor GPR40 has emerged as a potential target for type II diabetes because it has been hypothesized to participate in the adverse effects of chronic fatty acid exposure on function of beta-cell. Results: This signifies that G-protein-coupled receptors have recently emerged as novel therapeutic targets in metabolic diseases, such as diabetes, obesity and the metabolic syndrome. Therefore it seems natural that GPR40 represents a potentially attractive target to best meet the need for novel treatments for Type II diabetes. Conclusion: This review describes recent advances and novel drug discovery approaches in the antidiabetic area, focusing on GPR40 modulators which have been synthesized till date and their Structure-Activity Relationship (SAR).

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Phthalazine – Wikipedia,
Phthalazine | C8H6N399 – PubChem

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Ultrasound and microwave assisted synthesis of dihydroxyacetophenone derivatives with or without 1,2-diazine skeleton

A thorough study concerning O-alkylation and alpha-bromination of dihydroxyacetophenone (DA) and N-alkylation of 1,2-diazine, under ultrasound (US) and microwave (MW) irradiation as well as under conventional thermal heating (TH) is presented. Under US and MW irradiation the yields are higher, the amount of used solvent decreases substantially, the reaction time decreases considerable (from hours or days to minutes) and the consumed energy decreases, consequently the O-alkylation, alpha-bromination and N-alkylation methods could be considered environmentally friendly. A selective and efficient way to either bis-O-alkylation or mono-O-alkylation of DA has been found, the relative position of the two hydroxyl groups on the phenyl moiety being compulsory. A selective and efficient way for alpha-bromination in heterogeneous catalysis of DA derivatives under US irradiation is presented. The N-alkylation reaction of DA under US and MW irradiation proved to be the most convenient setup procedure for these types of reactions. Overall, the use of US proved to be more efficient than MW or TH.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N501 – PubChem

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A pepducin designed to modulate P2Y2R function interacts with FPR2 in human neutrophils and transfers ATP to an NADPH-oxidase-activating ligand through a receptor cross-talk mechanism

Several G-protein-coupled receptors (GPCRs) can be activated or inhibited in a specific manner by membrane-permeable pepducins, which are short palmitoylated peptides with amino acid sequences identical to an intracellular domain of the receptor to be targeted. Unlike the endogenous P2Y2R agonist ATP, the P2Y2PalIC2 pepducin, which has an amino acid sequence corresponding to the second intracellular loop of the human ATP receptor (P2Y2R), activated the superoxide anion-generating NADPH-oxidase in neutrophils. In addition to having a direct effect on neutrophils, the P2Y2R pepducin converted naive neutrophils to a primed state, which secondarily responded to ATP by producing superoxide. A pepducin with a peptide identical to the third intracellular loop of P2Y2R (P2Y2PalIC3) exhibited the same basic functions as P2Y2PalIC2, whereas one with a peptide that was identical to the first intracellular loop (P2Y2PalIC1) lacked these functions. The responses induced in neutrophils by the P2Y2R pepducins were not inhibited by the P2Y2R antagonist AR-C118925, and the receptor desensitization profile suggested the involvement of FPR2 rather than P2Y2R. Accordingly, antagonists/inhibitors of FPR2 attenuated the activities of the P2Y2R pepducins, which also selectively activated FPR2-overexpressing cells. In summary, we show that pepducins supposed to target P2Y2R activate human neutrophils through FPR2. We also show that the P2Y2PalIC2 pepducin can convert ATP from a non-activating agent to a potent neutrophil NADPH-oxidase activator. The molecular basis of this phenomenon involves cross-talk between the receptor/ligand pairs of P2Y2R/ATP and FPR2/P2Y2-pepducin.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N556 – PubChem

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Process and apparatus for producing ketoisophorone

beta-isophorone is formed by isomerizing alpha-isophorone in the presence of an isomerizing catalyst (an aliphatic C5-20 polycarboxylic acid) in an isomerizing-reaction unit 1. The beta-isophorone thus formed is oxidized with oxygen in an inert solvent in the presence of an oxidizing catalyst (a complex salt of a transition metal and an N,N’-disalicylidenediamine) in an oxidizing-reaction unit 2, thereby forming ketoisophorone. After removing a low-boiling point component, which is an impurity (non-conjugated cyclic ketone), from the reaction mixture using a distilling unit 3, a high-boiling component (oxidizing catalyst) is separated in a distilling unit 4, and then ketoisophorone is separated from the solvent in the separation unit 5. Thereafter, the solvent containing 0 to 5,000 ppm (weight basis) of the impurities and substantially free from ketoisophorone is recycled to the oxidizing reaction through a recycling line 6. According to the present invention, the combination of the isomerizing reaction and the oxidizing reaction makes it possible to produce ketoisophorone from alpha-isophorone while maintaining the activity of the oxydizing catalyst.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N12 – PubChem