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Copper(I) cyanide networks: Synthesis, luminescence behavior and thermal analysis. Part 1. Diimine ligands

Metal-organic networks of CuCN with diimines (L) = pyrazine (Pyz), 2-aminopyrazine (PyzNH2), quinoxaline (Qox), phenazine (Phz), 4,4?-bipyridyl (Bpy), pyrimidine (Pym), 2-aminopyrimidine (PymNH 2), 2,4-diaminopyrimidine (Pym(NH2)2), 2,4,6-triaminopyrimidine (Pym(NH2)3), quinazoline (Qnz), pyridazine (Pdz), and phthalazine (Ptz) were studied. Open reflux reactions produced complexes (CuCN)2(L) for L = Qox, Phz, Bpy, PymNH 2, Pym(NH2)2, Qnz, and Pdz and (CuCN) 3(L) complexes for L = Pyz, PyzNH2, Qox, Bpy, Pym(NH 2)3,l and Pdz. Also produced were (CuCN) 3(Pyz)2, (CuCN)(PyZNH2), (CuCN) 7(Pym)2, (CuCN)5(Qnz) 2 and (CuCN)5(Ptz)2. X-ray structures are presented for (CuCN)2(Pdz), (CuCN)2(PymNH2), and (CuCN) 7(Pym)2. Hydrothermal reactions yielded additional X-ray structures of (CuCN)2(PyzNH2), (CuCN) 3(Pym(NH2)2), (CuCN)4(Qnz), a second (CuCN)2(Pdz) phase, (CuCN)5(Pdz)2, (CuCN) 2(Ptz), and (CuCN)7(Ptz)2. Structural trends, including cuprophilic interactions and cyano-bridged Cu2(CN) 2 dimer formation, are discussed. Particularly short Cu…Cu interactions are noted for the novel 4- and 5-coordinate Cu2-(CN) 2 dimers. Thermal analyses show that most of the complexes decompose with loss of L around 160-180C. Luminescence behavior is relatively weak in the products.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N450 – PubChem

More research is needed about Phthalazine

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One-pot synthesis of phthalazines and pyridazino-aromatics: A novel strategy for substituted naphthalenes

A new one-pot strategy for the synthesis of phthalazines and pyridazino-aromatics starting from aromatic aldehydes has been developed. A variety of substituents ranging from electron withdrawing to donating is tolerated furnishing the desired 1,2-diazine in good to excellent yields. The products have been applied to the bidentate Lewis acid catalyzed inverse electron-demand Diels-Alder (IEDDA) reaction opening a novel two-step entry into substituted naphthalenes, such as Naproxen.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N231 – PubChem

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PHTHALAZINE DERIVATIVES FROM AROMATIC ALDAZINES

A Lewis acid mediated synthesis of phthalazine derivatives II and III from aromatic aldazines I is reported.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N367 – PubChem

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Sonogashira Reaction: Synthesis of Novel Derivatives of 3-Aryl-Substituted 6-Chloroimidazo[2, 1-a]phthalazines Catalyzed by Pd-Cu in Water

The reaction of 1-chloro-4-propargylaminophthalazine with various aryl halides catalyzed by Pd?Cu in the presence of potassium carbonate, as the base, in water leads to the one-pot formation of new derivatives of 3-aryl-substituted-6-chloroimidazo-[2, 1-a]phthalazines in moderate-to-good yields. Their structures are confirmed by IR and NMR spectra as well as elemental analyses. All the compounds prepared are screened in vitro for their anti-bacterial activities. The preliminary results indicate that some target compounds exhibit promising anti-bacterial potency.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N51 – PubChem

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Reaction of six-membered azaaromatics with allyltributyltin

Pyridazines were reacted with allyltributyltin in the presence of chloroformate to give 1-alkoxycarbonyl-6-allyl and 1-alkoxycarbonyl-4-allyldihydropyridazines as major and minor products, respectively. The reaction system was applied to other diazines and pyrimidine and pyrazine were shown to afford diallyltetrahydroadducts. Benzodiazines also gave allylation products in good yields. The reaction seems to be applicable to most six-membered azaaromatics.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N206 – PubChem

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Evaluation of new dihydrophthalazine-appended 2,4-diaminopyrimidines against Bacillus anthracis: Improved syntheses using a new pincer complex

The synthesis and evaluation of ten new dihydrophthalazine-appended 2,4-diaminopyrimidines as potential drugs to treat Bacillus anthracis is reported. An improved synthesis utilizing a new pincer catalyst, dichlorobis[1-(dicyclohexylphosphanyl)-piperidine]palladium(II), allows the final Heck coupling to be performed at 90C using triethylamine as the base. These milder conditions have been used to achieve improved yields for new and previously reported substrates with functional groups that degrade or react at the normal 140C reaction temperature. An analytical protocol for separating the S and R enantiomers of two of the most active compounds is also disclosed. Finally, the X-ray structure for the most active enantiomer of the lead compound, (S)-RAB1, is given.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N304 – PubChem

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FACILE RADICAL DECARBOXYLATIVE ALKYLATION OF HETEROAROMATIC BASES USING CARBOXYLIC ACIDS AND TRIVALENT IODINE COMPOUNDS

Many kinds of heteroaromatic bases were easily alkylated by the reaction of carboxylic acids with benzene or pentafluorobenzene via radical decarboxylative pathways.This system was further applied to the reaction with tetrahydrofurylcarboxylic acid, 1-(2,3,5-tri-O-benzyl)-D-ribofuranosylacetic acid, and 1-(2,3,5-tri-O-benzyl)-D-ribofuranosylcarboxylic acid for the model synthesis of C-nucleosides.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N449 – PubChem

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Novel triazolophthalazine-hydrazone hybrids as potential PCAF inhibitors: Design, synthesis, in vitro anticancer evaluation, apoptosis, and molecular docking studies

Three novel series of triazolophthalazine derivatives bearing hydrazone moiety were designed, synthesized, and evaluated for their anticancer activity against four human cancer cell lines by MTT assay. Six derivatives demonstrated comparable activity with Doxorubicin reference drug against the selected cancer cells. Especially, compound 16 showed the most potent activity with IC50 values of 5.70, 8.04, 11.15, and 4.25, muM against HePG2, MCF-7, PC3, and HCT-116 respectively. Also, compound 26 exhibited comparable inhibitory effect with that of Doxorubicin against the selected cancer cell lines with IC50 values of 6.45, 8.63, 12.28, and 7.03 muM against HePG2, MCF-7, PC3, and HCT-116 respectively. Investigation of the apoptotic activity of the two most active compounds revealed that compounds 16 and 26 could induce both the early and the late apoptosis of HePG2. Further mechanistic study of the HePG2 cell cycle confirmed the spectacular cytotoxic and apoptotic effects of both compounds. Compounds 16 and 26 showed a pronounced increase in cells in G2/M and Pre G1 phases with a concomitant reduction of cells in G0-G1 and S phases. A follow up enzymatic assay indicated that these two compounds have comparable activities with that of bromosporine as PCAF inhibitors with IC50 values of 8.13 and 5.31 muM respectively. Moreover, molecular docking study for all the synthesized compounds was performed to predict their binding affinities toward the active site of histone acetyltransferase GCN5. Results of molecular docking were strongly correlated with that of the cytotoxicity study.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N18 – PubChem

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Hydrazide derivatives of luminol for chemiluminescence-labelling of macromolecules

A series of chemiluminescent compounds containing a hydrazide group as a nucleophilic functional group has been synthesized. The syntheses were started from chemiluminescent luminol and isoluminol. The linker moiety was easily introduced onto non-nucleophilic exocyclic amino groups of luminol and isoluminol by gentle heating with cyclic acid anhydrides such as glutaric anhydride. The resulting carboxy group was converted to hydrazide by a simple condensation reaction using carbodiimide. Although majority of the synthesized compounds did not emit strong light, a sufficient chemiluminescence intensity was obtained from luminolamido- C2-hydrazide (L2H) comprising of luminol scaffold with a dimethylene linker. The ability of L2H to form a covalent bond with a macromolecule was further investigated by incubation with oxidized horseradish peroxidase. The analysis on matrix assisted laser desorption/ionization-time of flight (MALDI-TOF) MS revealed that the coupling efficiency of L2H was similar to that of commercially available labelling reagent having a hydrazide group. These results suggested that L2H, the luminol hydrazide containing a dimethylene linker, could be useful for the labelling of macromolecules in the sensitive bioassay such as chemiluminescence immunoassay.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N634 – PubChem

Brief introduction of 6-Amino-2,3-dihydrophthalazine-1,4-dione

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[29] Enhanced chemiluminescent reactions catalyzed by horseradish peroxidase

Enhancement of light emission from the horseradish peroxidase-catalyzed oxidation of diacyl hydrazides on addition of 6-hydroxybenzothiazole or phenol derivatives forms the basis of rapid, specific, and sensitive chemiluminescent assays for peroxidase. The advantages and wide applicability of the technique have been demonstrated in a range of ligand-binding assays. Careful selection of chemiluminescent reagents, enhancer, their relative proportions and reaction conditions, and more detailed knowledge of the mechanism of enhancement should enable further improvements in sensitivity and the intensity or constancy of light emission.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N642 – PubChem