Extracurricular laboratory:new discovery of Phthalazine

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Synthesis, Structure, and Biological Activity of New Azine-Bridged Dinuclear Platinum(II) Complexes – A New Class of Anticancer Compounds

A recently described new class of dinuclear platinum anticancer compounds, represented so far by the isomeric azine-bridged complexes [{cis-Pt(NH 3)2Cl}2(mu-pzn)]Cl2 (1) (pzn = pyrazine), [{cis-Pt(NH3)2Cl)2(mu-pmn)]Cl 2 (2) (pmn = pyrimidine) and [{cis-Pt(NH3) 2Cl}2(mu-pdn)](NO3)2 (3) (pdn = pyridazine), has been added to. Three new dinuclear complexes of this type, [{cis-Pt(NH3)2Cl}2(mu-2,5pzn)]Cl2 (4) (2,5pzn = 2,5-dimethylpyrazine), [{cis-Pt(NH3) 2Cl)2(mu-qzn)]Cl2 (5) (qzn = quinazoline), and [{cis-Pt(NH3)2Cl}2(mu-pht)](NO 3)2 (6) (pht = phthalazine), have been newly synthesized and characterized by 1H and 195Pt NMR spectroscopy. The interaction of the new compounds with 2 equiv. of 9EtG in D2O at 310 K has been investigated. Complexes 4 and 5 undergo substitution of both chloride ligands by 9EtG similarly to the related complexes 1 and 2, respectively. The methyl substituents on the pyrazine ring induce steric hindrance in 4 resulting in a slower reaction rate as compared to 1. Similarly to the case of 3, interaction of complex 6 with 9EtG results in cleavage of the Pt-N(pht) bond and subsequent formation of the polymeric species. A cytotoxicity assay of 4-6 has been performed on seven human tumor cell lines and on L1210 murine leukemia cell lines, sensitive and resistant to cisplatin. Compounds 4 and 5 exhibit lower cytotoxicity than the analogous complexes with unsubstituted azines. Complex 6 is more active: its cytotoxicity in the L1210 cell lines is similar to that of cisplatin. Analysis of nuclear DNA fragmentation in L1210 cells treated with the azine-bridged complexes 1-6 has been carried out. The results clearly indicate induction of apoptosis by all the compounds, implying considerable anticancer potential. The structure-activity relationship for this class of dinuclear platinum(ii) complexes is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N218 – PubChem

A new application about Phthalazine

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Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones

A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N471 – PubChem

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Synthesis and cytotoxic evaluation of some new 3-(2-(2-phenylthiazol-4-yl) ethyl)-quinazolin-4(3H) one derivatives with potential anticancer effects

Quinazolinones are a group of heterocyclic compounds that have important biological activities such as cytotoxicity, anti-bacterial, and anti-fungal effects. Thiazole-containing compounds have also many biological effects including antitumor, antibacterial, anti-inflammatory, and analgesic activities. Due to significant cytotoxic effects of both quinazoline and thiazole derivatives, in this work a group of quinazolinone-thiazol hybrids were prepared and their cytotoxic effects on three cell lines were evaluated using MTT assay. Compounds A3, A2 , B4 , and A1 showed highest cytotoxic activities against PC3 cell line. Compounds A3 , A5 , and A2 were most active against MCF-7 and A3 , A5 , and A6 showed good cytotoxic effect on HT-29 cell line. According to the results, A3 efficiently inhibited all cell growth tested in a dose dependent manner. The IC 50 of A3 was 10 M, 10 muM, and 12muM on PC3, MCF-7, and HT-29 cells, respectively.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N191 – PubChem

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From Thorium to Plutonium: Trends in Actinide(IV) Chloride Structural Chemistry

A series of eighteen tetravalent actinide (An = Th, U, Pu) compounds were synthesized from acidic aqueous solutions containing thorium, uranium, or plutonium and a series of protonated nitrogen heterocycles. The compounds were characterized using Raman, IR, and optical absorption spectroscopies. The structures were determined using single-crystal X-ray diffraction and found to consist of [An(H2O)xCly]4-y (x = 4-7 and y = 2-4) or AnCl62- molecular units. Breaks in the structural chemistry of the early actinides were observed, with Th adopting exclusively Th-aquo-chloro species and Pu forming only PuCl62- U crystallized as both U-aquo-chloro and UCl62-. The relationship between the solid-state structural units and the solution species was interrogated using UV-vis-near-IR absorption spectroscopy. A comparison of the solution and solid-state spectra suggested that, although prevalent in the solid state, particularly for U and Pu, AnCl62- does not exist to an appreciable extent in the reaction solution. Despite the identification of U-aquo-chloro species in solution, there are limited reports of these complexes in the solid state. Isolation of these unique actinide(IV) chlorides as reported in this work may point to the importance of nonbonding interactions in the stabilization and precipitation of AnIV structural units.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N463 – PubChem

Simple exploration of 2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid

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Electric Literature of 763114-26-7, Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Patent, and a compound is mentioned, 763114-26-7, 2-Fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzoic acid, introducing its new discovery.

Such pyridazinone compounds and its preparation and use (by machine translation)

The invention relates to a kind of the following formula I said pyridazinone compound, preparation method thereof and its in preparation for preventing or treating the ribose poly-ADP – ribose polymerase (PARP) related disease in use. (by machine translation)

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Phthalazine – Wikipedia,
Phthalazine | C8H6N780 – PubChem

More research is needed about 3682-14-2

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Selective inhibition of extracellular oxidants liberated from human neutrophils – A new mechanism potentially involved in the anti-inflammatory activity of hydroxychloroquine

Hydroxychloroquine is used in the therapy of rheumatoid arthritis or lupus erythematosus. Although these diseases are often accompanied by activation of neutrophils, there are still few data relating to the impact of hydroxychloroquine on these cells. We investigated the effect of orally administered hydroxychloroquine on neutrophil oxidative burst in rats with adjuvant arthritis. In human neutrophils, extra- and intracellular formation of oxidants, mobilisation of intracellular calcium and the phosphorylation of proteins regulating NADPH oxidase assembly were analysed. Administration of hydroxychloroquine decreased the concentration of oxidants in blood of arthritic rats. The inhibition was comparable with the reference drug methotrexate, yet it was not accompanied by a reduction in neutrophil count. When both drugs were co-applied, the effect became more pronounced. In isolated human neutrophils, treatment with hydroxychloroquine resulted in reduced mobilisation of intracellular calcium, diminished concentration of external oxidants and in decreased phosphorylation of Ca2 +-dependent protein kinase C isoforms PKCalpha and PKCbetaII, which regulate activation of NADPH oxidase on plasma membrane. On the other hand, no reduction was observed in intracellular oxidants or in the phosphorylation of p40phox and PKCdelta, two proteins directing the oxidase assembly to intracellular membranes. Hydroxychloroquine reduced neutrophil-derived oxidants potentially involved in tissue damage and protected those capable to suppress inflammation. The observed effects may represent a new mechanism involved in the anti-inflammatory activity of this drug.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N578 – PubChem

More research is needed about 253-52-1

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Direct selective oxidative cross-coupling of simple alkanes with heteroarenes

A dream reaction: An efficient and practical method for the oxidative cross-coupling of heteroaromatic compounds and simple alkanes has been developed. The desired products are smoothly and regioselectively formed under mild reaction conditions at ambient temperature in a hypervalent-iodine-mediated transformation. The method allows for preferential transformation of stronger C sp 3-H bonds in the presence of weaker C sp 3-H bonds under metal-free conditions.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N39 – PubChem

More research is needed about 253-52-1

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Excited state absorption spectra and intersystem crossing kinetics in diazanaphthalenes

Picosecond time-resolved, excited state absorption spectra in the visible following excitation at 355 nm are discussed for room temperature solutions of four diazanaphthalenes (DN)-quinoxaline (1,4-DN), quinazoline (1,3-DN), cinnoline (1,2-DN), and phthalazine (2,3-DN).Kinetics of singlet state decay are obtained by monitoring the decay of Sn <*> S1 bands.The intersystem crossing rate constant (kisc) is found to vary as kisc(1,4-DN)>kisc(1,3-DN)>kisc(1,2-DN).The kisc in phthalazine could not be determined from the weak, visible Sn<*>S1 absorption.Assuming rapid singlet vibrational relaxation and only minor effects due to energy gap variations, these experimental results agree with statistical limit predictions for the relative nonradiative rate.Calculations of the spin-orbit coupling matrix element betael = <*>so<*>T1(3??*)>, using INDO wave functions, give the ordering betael(1,4-DN)>betael(2,3-DN)>betael(1,3-DN)>betael(1,2-DN).

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Phthalazine – Wikipedia,
Phthalazine | C8H6N394 – PubChem

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Interaction of some new 2-(substituted-thio)-quinazolin-4-ones with molybdenum hydroxylases: A pharmacophore prediction

Background Molybdenum hydroxylases have been implicated as key oxidative enzymes in some diseases. Methods Twenty 2-(substituted-thio)-quinazolin-4-one derivatives recently synthesized in our laboratory were examined for their inhibitory activity toward molybdenum hydroxylases. Results and conclusion The tested quinazolines inhibited both xanthine oxidase and aldehyde oxidase enzymes in a competitive pattern with Ki values range of 66-753 muM. Pharmacophore prediction methodology was used to study the structure requirements of those inhibitors.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N141 – PubChem

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Red to near-infrared organometallic phosphorescent dyes for OLED applications

In modern research on organic light-emitting diodes (OLEDs), cyclometalated iridium(III) complexes represent one of the most studied class of compounds. The high emission efficiency caused by the strong spin-orbit coupling in the presence of heavy metals leads to the mixing of singlet and triplet manifolds so that both the singlet and triplet excitons can be harvested. For OLEDs to be useful in displays application, true red, green, and blue emissions of sufficient luminous efficiencies and proper chromaticity are required. In recent years, the development of materials for phosphorescent red OLEDs has indeed gone through several important evolutional stages. However, the luminescent quantum yields of red-emitting iridium(III) phosphors tend to be intrinsically low which are governed by the energy gap law for triplet states in which the luminescence quantum yields tend to decrease with an increase in the emission wavelength. Many red organic dyes currently in use do not show a good compromise between device efficiency and color purity. In general, a dilemma facing red OLEDs was realized in which efficient and bright dopants are not red enough, and red-enough dopants are not efficient and bright. In this review article, we highlight the recent progress and current challenges of efficient OLEDs based on cyclometalated iridium(III) dyes which exhibit saturated red and near-infrared electroluminescence. Optimization of the phosphorescent red OLED efficiency/color purity trade-off and extension of the work to other organometallic phosphors are also presented and discussed.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N185 – PubChem