Experimental study on the thermochemistry of 1-(2H)-phthalazinone and phthalhydrazide

Silva, Manuel A.V. Ribeiro da; Cabral, Joana I.T.A.

doi:10.1016/j.jct.2008.01.010

Cited by 10 publications

(1 citation statement)

References 21 publications

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“…There is reported in the literature the standard molar enthalpy of formation of an isomer of quinazoline-2,4(1 H ,3 H )-dione, 2,3-dihydrophthalazine-1,4-dione (phthalhydrazide), Δ f H m o (g) = −(107.4 ± 2.4) kJ·mol –1 . The experimental enthalpy for the isomerization reaction: (163.7 ± 4.1) kJ·mol –1 is in very good agreement with the value obtained from computational calculations at the G3(MP2)//B3LYP level: 168.2 kJ·mol –1 .…”

Section: Computational Results and Discussionsupporting

confidence: 83%

Energetics of Quinazoline-2,4(1H,3H)-dione: An Experimental and Computational Study

et al. 2011

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In this paper we report the standard (p°= 0.1 MPa) molar enthalpy of formation of quinazoline-2,4(1H,3H)-dione, in the gaseous phase, at T = 298.15 K, which was derived from a combined experimental and computational thermochemical work. The static bomb combustion calorimetry technique was used to determine the standard massic energy of combustion and consequently the standard molar enthalpy of formation, in the crystalline phase, at T = 298.15 K, and the Calvet microcalorimetry technique was employed to determine the standard molar enthalpy of sublimation, at T = 298.15 K. The obtained standard molar enthalpy of formation, in the gaseous phase, at T = 298.15 K, was:3) kJ 3 mol À1 . In addition, quantum chemical calculations were performed using the G3(MP2)//B3LYP composite method to assess the relative energetic stabilities of quinazoline-2,4(1H,3H)-dione and its tautomers (4-hydroxyquinazolin-2(1H)-one, 2-hydroxyquinazolin-4(1H)-one, 2-hydroxyquinazolin-4(3H)-one, and quinazolin-2,4-diol). Estimates of the standard molar enthalpy of formation, in the gaseous phase, of the most stable tautomer, quinazoline-2,4(1H,3H)dione, at T = 298.15 K, were obtained from the G3(MP2)//B3LYP calculations using appropriate isodesmic reactions and were further compared with the obtained experimental value. The aromaticity of quinazoline-2,4(1H,3H)-dione has also been assessed through the evaluation and analysis of the Nucleus Independent Chemical Shifts (NICS) and their most significant components for the benzene and pyrimidine rings.

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Section: Computational Results and Discussionsupporting

confidence: 83%

Energetics of Quinazoline-2,4(1H,3H)-dione: An Experimental and Computational Study

et al. 2011

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Design, synthesis, biological evaluation, and molecular modeling simulations of new phthalazine‐1,4‐dione derivatives as anti‐Alzheimer's agents

Nuha,

Evren,

Özkan

et al. 2024

Archiv der Pharmazie

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The development of targeted phthalazine‐1,4‐dione acetylcholinesterase (AChE) inhibitors for treating Alzheimer's disease involved the synthesis of 32 compounds via a multistage process. Various analytical techniques confirmed the compounds' identities. Thirteen compounds were found to inhibit AChE by more than 50% without affecting butyrylcholinesterase (BChE). Among these, three compounds, 8m, 8n, and 8p, exhibited extraordinary activity similar to donepezil, a reference AChE inhibitor. During enzyme kinetic studies, compound 8n, displaying the highest AChE inhibitory activity, underwent evaluation at three concentrations (2 × IC50, IC50, and IC50/2). Lineweaver–Burk plots indicated mixed inhibition activity for compound 8n against AChE, suggesting a combination of competitive and noncompetitive characteristics. Additionally, effective derivatives 8m, 8n, and 8p exhibited high blood–brain barrier (BBB) permeability in in vitro parallel artificial membrane permeability assay tests. Molecular docking studies revealed that these compounds bind to the enzyme's active site residues in a position similar to donepezil. Molecular dynamic simulations confirmed the stability of the protein–ligand system, and the chemical reactivity characteristics of the compounds were investigated using density functional theory. The compounds' wide energy gaps suggest stability and therapeutic potential. This research represents a significant step toward finding a potential cure for Alzheimer's disease. However, further research and testing are required to determine the compounds' safety and efficacy. The unique structure of phthalazine derivatives makes them suitable for various biological activities, and these compounds show promise for developing effective drugs for treating Alzheimer's disease. Overall, the development of these targeted compounds is a crucial advancement in the search for an effective treatment for Alzheimer's disease.

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Interplay of thermochemistry and Structural Chemistry, the journal (volume 16, 2005) and the discipline

et al. 2010

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Experimental study on the thermochemistry of 1-(2H)-phthalazinone and phthalhydrazide

Cited by 10 publications

References 21 publications

Energetics of Quinazoline-2,4(1H,3H)-dione: An Experimental and Computational Study

Energetics of Quinazoline-2,4(1H,3H)-dione: An Experimental and Computational Study

Design, synthesis, biological evaluation, and molecular modeling simulations of new phthalazine‐1,4‐dione derivatives as anti‐Alzheimer's agents

Interplay of thermochemistry and Structural Chemistry, the journal (volume 16, 2005) and the discipline

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