Simple exploration of 6-Amino-2,3-dihydrophthalazine-1,4-dione

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Pharmacological intervention with oxidative burst in human neutrophils

In this study we investigated the effect of five therapeutically used drugs and four natural polyphenolic compounds on the mechanism of oxidative burst of human neutrophils concerning their participation in the generation of reactive oxygen species (ROS). The compounds investigated decreased the oxidative burst of whole blood in the rank order of potency: N-feruloylserotonin > quercetin > curcumin > arbutin > dithiaden > carvedilol. The generation of intracellular reactive oxygen species in isolated neutrophils decreased in the same rank order, while carvedilol was ineffective. Scavenging of extracellular oxygen radicals followed the rank order of potency: N-feruloylserotonin > curcumin > quercetin > dithiaden. Arbutin and carvedilol had no effect. All compounds tested increased the activity of caspase-3 in cell-free system indicating a positive effect on apoptosis of neutrophils. Activation of protein kinase C was significantly decreased by dithiaden, curcumin, quercetin and N-feruloylserotonin. Carvedilol, dithiaden, quercetin and arbutin reduced activated neutrophil myeloperoxidase release more significantly compared with their less pronounced effect on superoxide generation The presented results are indicative of pharmacological intervention with neutrophils in pathological processes. Of particular interest was the effect of natural compounds. Intracellular inhibition of oxidative burst in isolated neutrophils by the drugs tested and natural antioxidants has to be further analysed since ROS play an important role in immunological responses of neutrophils.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N612 – PubChem

Discovery of Phthalazine

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A new photochromic system based on a pyridazinopyrrolo[1,2-b]pyridazine with ultrafast thermal decoloration

The nucleophilic addition of the substituted pyridazines 2a-e to diacetylspirocyclopropene (1) in dry ether solution afforded the dihydroindolizines 3a-e, which undergo ring opening to the betaine 3?a-e after irradation with UV light. Condensation of the diacetyl groups of the dihydroindolizines (DHIs) 3a-e with hydrazine hydrate in a diethyl ether/ethanol mixture gave the new pyridazinopyrrolo[1,2-b]pyridazines 4a-e. Compounds 4a-e showed no photochromism at room temperature or after cooling with liquid nitrogen. However laser flash spectroscopy was successfully used for the determination of both the half-life and absorption maxima of the betaines 4?a-e.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N155 – PubChem

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Assorted applications of N-substituted-2,4-thiazolidinediones in various pathological conditions

Thiazolidine-2,4-dione (TZD) is one of the most frequently encountered heterocyclic rings which has been implicated in design and synthesis of entities for various pathogenic conditions including cancer. Since its discovery various substitutions at 5th position have been carried out and reviewed. Various substitutions at 5th position have led to generation of glitazones, whose target peroxisome proliferating activated receptor gamma (PPARgamma) was found decade after their discovery. Acidic hydrogen (-NH) of TZD is a prime pharmacophoric requirement for the activation of PPARgamma. However, advanced in-silico techniques have helped to design compounds bearing substitutions at both methylene and -NH group of TZD, targeting range of enzymes involved in various pathological conditions viz., diabetes, hyperlipidemia, infectious disease, inflammation and cancer. The promising activities shown by methylene and N-substituted TZDs in above mentioned therapeutic areas, prompted us to collate the information which would help researchers to alter the structure of existing ligands and to design new TZD derivatives with better safety and efficacy profiles.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N865 – PubChem

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Fragmentation Reactions of Molecular Dications of Aromatic Heterocyclic Fused-ring Compounds Containing More Than One Nitrogen Atom

Fragmentation reactions of both metastable and collisionally activated dications, formed by electron impact ionization of heterocyclic fused-ring aromatic compounds containing more than one nitrogen atom, were investigated.This work is an extension of similar work on analogous compounds containing just one nitrogen atom and on the related polycyclic aromatic hydrocarbons.The results obtained are interpreted in terms of mechanistic proposals concerning the competition between charge-separation and neutral-expulsion reactions, based on variations in diradical characterwith increasing molecular size and nitrogen content of these molecular dications.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N339 – PubChem

Final Thoughts on Chemistry for Phthalazine

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Self-assembly of ID- And 3D-networks through non-coordination intermodular forces: Synthesis and crystal structures of copper(I) complexes based on pyridazine-type ligands

Reaction of [Cu2(H3CCN)2(mu-pydz) 3][PF6]2 (1) with an excess of pyridazine or phthalazine yielded the novel dinuclear complexes [Cu2(mu-pydz) 3(pydz)2][PF6]2 (2) and [Cu 2(mupydz)(mu-phtz)2(phtz)2][PF 6]2 (5), respectively. Depolymerisation of the coordination polymer ?1{[Cu(mu-pydz) 2][PF6]} (3) in dichloromethane by addition of an excess of benzo[c]cinnoline afforded the dinuclear copper(I) salt [Cu 2(mu-pydz)2(pydz)2(benzo[c]cinnoline) 2][PF6]2 (4). Furthermore, a new route for the preparation of bis(benzonitrile)tris(mu-phthalazine)dicopper(I) bis(trifluoromethanesulfonate), [Cu2(C6H 5CN)2(i-phtz)3][CF3SO 3]2 (7), was established from {[Cu(CF3SO 3)]2 ¡¤C6H5Me}, phthalazine and benzonitrile via the very air-sensitive intermediate [Cu2(CF 3SO3)2(mu-phtz)3] (6). Copper(I) compounds 2, 4, and 7 were completely characterised and the molecular structures confirmed in the solid state by single-crystal X-ray structure determination. The analysis of the packing of the molecules in crystals of 4 and 7 revealed a self-assembly of oneand three-dimensional frameworks, respectively, resulting from intermolecular pi-pi stacking interactions between pyridazine-type ligands.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N343 – PubChem

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Synthesis and Anticonvulsant Activity Evaluation of Phthalazine and Heterocyclic Derivatives

Four series of derivatives, 6-substituted-1,2,4-triazolo[3,4-a] phthalazine derivatives and 6-substituted tetrazolo[5,1-a]phthalazine derivatives have been synthesized. The structures of compounds are confirmed by 1H NMR, 13C NMR, IR and HRMS. The anticonvulsant effects of the compounds are evaluated with maximal electroshock test by intraperitoneally injected in mice. The experimental results show that N-(4-bromophenyl)tetrazolo[5,1-a]phthalazin-6-amine (7a) was the most potent compound, with a median effective dose of 5.89 mg¡¤kg-1. Its anticonvulsant effect is better than the reference drug, carbamazepine.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N506 – PubChem

Extended knowledge of Phthalazine

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Synthesis, biological, anti-inflammatory activities and quantum chemical calculation of some [4-(2, 4, 6-trimethylphenyl)-1(2H)-oxo-phthalazin-2yl] acetic acid hydrazide derivatives

The phthalazine carbohydrazide 2 was prepared and incorporated into the corresponding 1,2,4-triazole and carbamate derivatives. Phthalazine carboxylic acid hydrazide 2 was treated with isatine and cyclo-hexanone to give the corresponding hydrazone derivatives 16, 19 in good yields. Furthermore, alpha-amino acid derivative conjugated with 1-oxophthalazine moiety 35 was synthesized by the reaction of the corresponding aizde 28, via the azide-coupling method, with glycine methyl ester. The peptide ester 35 was converted into their corresponding amide 36 by treating with methanolic ammonia. Moreover, 35 was boiled with hydrazine hydrate to afford the corresponding hydrazide 37. Finally, the dipeptide 38 was prepared by coupling of 35 with L-alanine methyl ester. Some of these compounds were screened in vitro for their antimicrobial activity. The energy gap between the highest occupied molecular orbital and lowest unoccupied molecular orbital has been calculated using the theoretical computations to reflect the chemical reactivity and kinetic stability of compounds.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N140 – PubChem

The Absolute Best Science Experiment for Phthalazine

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Combining Bidentate Lewis Acid Catalysis and Photochemistry: Formal Insertion of o-Xylene into an Enamine Double Bond

A bidentate Lewis acid catalyzed domino inverse-electron-demand Diels-Alder reaction combined with a photoinduced ring opening formally inserts o-xylene moieties into enamine double bonds. After reduction, phenethylamines were obtained in good yields. The scope of the reaction was determined by variation of all three starting compounds: phthalazines, aldehydes, and amines.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N24 – PubChem

Simple exploration of Phthalazine

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Visible-Light-Induced Copper-Catalyzed Decarboxylative Coupling of Redox-Active Esters with N-Heteroarenes

Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxyphthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyridazine to give the corresponding products in modest to excellent yields. The reactions proceed under mild conditions and have a broad scope and high functional group tolerance. Mechanistic studies revealed that the catalytic behavior of CuI photocatalyst generated in situ was consistent with that of preformed [Cu(dmp)(xantphos)]BF4.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N271 – PubChem

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The importance of triazole scaffold in the development of anticonvulsant agents

Epilepsy is one of the most important neurological disorders with high prevalence worldwide. Many epileptic patients are not completely treated with available drugs and need multiple therapies. Also, many antiepileptic drugs have shown unwanted side effects and drug interactions. Therefore there are continuing interests to find new anticonvulsant drugs. Triazole ring has been found in the structure of many compounds with diverse biological effects. Due to the success of several triazole-containing drugs that entered the pharmaceutical market as CNS-active drugs, this class of heterocyclic compounds has great importance for discovery and development of new anticonvulsant drugs. In this article, we have tried to summarize the latest efforts which have been made in the design and development of triazole-derived anticonvulsant agents.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N47 – PubChem