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2H-Indazolo[2,1-b]phthalazine-trione derivatives: Inhibition on some metabolic enzymes and molecular docking studies

In this study, substituted 2H-indazolo[2,1-b]phthalazine-1,6,11-trione compounds (4a?d) obtained via one-pot three-component condensation reaction of aromatic aldehydes, cyclic 1,3-dione, and phthalhydrazide in ethanol catalyzed by Y(OTf)3 showed satisfactory inhibitory effects against some important enzymes. Also, these molecules had Ki values in the row of 185.92 ¡À 36.03-294.82 ¡À 50.76 nM vs carbonic anhydrase I (CA I), 204.93 ¡À 46.90-374.10 ¡À 83.63 nM against human CA II, 937.16 ¡À 205.82-1021.83 ¡À 193.66 nM against alpha-glycosidase (alpha-Gly), respectively. For cholinesterase enzymes, the Ki values were found in the range of 47.26 ¡À 9.62-72.05 ¡À 19.47 nM against acetylcholinesterase (AChE) and 65.03 ¡À 9.88-102.83 ¡À 25.04 nM against butyrylcholinesterase (BChE), respectively. The inhibition effects of these compounds against enzymes whose name are AChE, BChE, alpha-Gly, hCA I, and hCA II, were compared with control molecules like tacrine, acarbose, and acetazolamide.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N437 – PubChem

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Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides

The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.

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Phthalazine | C8H6N183 – PubChem

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[Bmim]OH mediated new synthesis 3-(1H-indol-3-yl)acrylonitrile derivatives

[Bmim]OH mediated new synthesis of 3-(1H-indol-3-yl)acrylonitrile derivatives 6 have been developed by the reaction of diethyl phthalate (1) with ethyl cyanoacetic acid hydrazide (2) to form 3-(1,4-dioxo-3,4-dihydrophthalazin-(1H)-yl)-3-oxopropanenitrile (3). Then compound 3 reacted with indole-3-aldehyde (4) by Knoevenagel condensation to form compound 2-(1,4-dioxo-1,2,3,4-tetrahydrophthalazine-2-carbonyl)-3-(1H-indol-3-yl)acrylonitriles (5). Compounds 5 undergo alkylation with alkylating agents to form 6 with good yields. Compounds 6 could also be synthesized by alkylation of 4 followed by condensation with 3.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N228 – PubChem

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The influence of hydrogen bonding on partition coefficients

This Perspective explores how consideration of hydrogen bonding can be used to both predict and better understand partition coefficients. It is shown how polarity of both compounds and substructures can be estimated from measured alkane/water partition coefficients. When polarity is defined in this manner, hydrogen bond donors are typically less polar than hydrogen bond acceptors. Analysis of alkane/water partition coefficients in conjunction with molecular electrostatic potential calculations suggests that aromatic chloro substituents may be less lipophilic than is generally believed and that some of the effect of chloro-substitution stems from making the aromatic pi-cloud less available to hydrogen bond donors. Relationships between polarity and calculated hydrogen bond basicity are derived for aromatic nitrogen and carbonyl oxygen. Aligned hydrogen bond acceptors appear to present special challenges for prediction of alkane/water partition coefficients and this may reflect ?frustration? of solvation resulting from overlapping hydration spheres. It is also shown how calculated hydrogen bond basicity can be used to model the effect of aromatic aza-substitution on octanol/water partition coefficients.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N79 – PubChem

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New pyrrolo[2,1-a]phthalazine derivatives by 1,3-dipolar cycloaddtion reactions

The esters of pyrrolo[2,1-a]phthalazine-1,2-dicarboxylic acid 13a-c were obtained from pthalazinium bromide 9, esters of acetylenedicarboxylic acid, triethylamine and tetrakis-pyridinocobalt(II) dichromate (TPCD) as oxidant The synthesis of pyrrolo[2,1-a]phthalazine-1-carboxylic esters from 9, acetylenemonocarboxylic acid esters and triethylamine was performed in the absence of TPCD. Structure proof for the new compunds is based on H-, C-NMR, COSY and Hetcor experiments.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N133 – PubChem

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Direct C-H Arylation of N-Heterocycles with Aryl Triazenes Using Molecular Oxygen as Oxidant

An efficient C?H arylation of N-heterocycles has been developed using stable and easily accessible aryl triazenes in the presence of oxygen under metal- and peroxide-free conditions. The methodology is regiospecific and applicable to a wide range of electron-deficient N-heterocycles and aryl triazenes as demonstrated by 20 examples with yields ranging from 32?83%.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N103 – PubChem

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Electron-transfer Reactions. I. The Application of Derivative Linear-sweep Voltammetry for the Determination of the Rate Constants for Electron Transfer between Two Different Organic Anion Radicals

The kinetic of homogeneous electron-transfer reactions between different anion radicals, A-. and B-. can be conveniently studied by derivative linear-sweep voltammetry under conditions where the dianions, B2-, are rapidly protonated. The method involves measurements of the ratio, R’I(A/B) = I’A/I’B, where I’A and I’B are the maximum values of dI/dt for the reduction of A and B, at different sweep rates for solutions containing both substrates.Working curves have been calculated by digital simulation for the concentration ratios, C0B/C0A = 1, 2, 5 and 10.The approximate kinetic range of the method is given by expression (ii). 104 < k1/(dm3 mol-1 s-1) < 108 (ii) The application of this type of measurement is illustrated by the electron transfer from the anion radicals, A-., of several aromatic compounds to the anion radicals, B-., of azobenzene and 4,4'-dimethylazobenzene.The fit of the experimental data to the working curves is generally excellent for substrates having similar diffusion coefficients.The measured rate constants vary from 2.5x106 dm3 mol-1 s-1, for A = phthalazine and B = azobenzene, to 2.7x104 dm-3 mol-1 s-1, for A = anthracene and B = 4,4'-dimethylazobenzene. We¡¯ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 253-52-1, and how the biochemistry of the body works.Application In Synthesis of Phthalazine

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Phthalazine – Wikipedia,
Phthalazine | C8H6N199 – PubChem

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Photochemical Reactions of Phthalazine in 2-Propanol

Phthalazine undergoes dual photoreactions to simultaneously give two photoproducts, 1,2-dihydrophthalazine (1) and 1,1′,2,2′-tetrahydro-1,1′-biphthalazine (2), upon ultraviolet light irradiation in 2-propanol under nitrogen.There occurs neither photochemical nor thermal interconversion between 1 and 2; these compounds are formed independently from a common intermediate through different reaction pathways.The results of quenching and sensitization experiments for both the reactions and the phosphorescence emission show that the lowest excited singlet and triplet states of phthalazine participate in the formation of 1 and 2, respectively.The observed photochemical behaviors under various conditions lead us to propose a reaction mechanism: Phthalazine is photoreduced in the S1 state to form 1,2-dihydro-1-phthalazinyl radical.The resulting radical in a solvent cage undergoes a subsequent hydrogen abstraction to form 1.On the other hand, the same radical produced in the T1 state escapes from the solvent cage to cause a dimerization which affords 2.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N202 – PubChem

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Tuning the Photophysical Properties of Push-Pull Azaheterocyclic Chromophores by Protonation: A Brief Overview of a French-Spanish-Czech Project

Conjugated push-pull molecules that incorporate nitrogen heterocycles as electron-withdrawing units are interesting materials because of their luminescence properties. These chromophores can be easily and reversibly protonated at the nitrogen atom of the heterocyclic ring and this can cause dramatic color changes. White and multi-color photoluminescence both in solution and in the solid state can be obtained by an accurate control of the amount of acid. Thus, with a suitable design these compounds have potential applications in the development of colorimetric pH sensors and the fabrication of OLEDs based on only one material. We provide here a brief overview of our collaborative efforts made in this area.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N19 – PubChem

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Synthesis and optical properties of a series of pyrrolopyridazine derivatives: Deep blue organic luminophors for electroluminescent devices

We describe a systematic study of a series of eight blue light-emitting molecules which can be prepared in one step from inexpensive commercial starting materials. The relative luminescence quantum yield can be as high as 84% and the heterocycles are luminescent in the condensed state, either as solids or as oils, indicating that there is no self-quenching in this system. The last observation augurs well for these heterocycles being useful in the fabrication of deep blue light-emitting devices.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N108 – PubChem