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Phthalimide

Phthalimide is a heterocyclic organic compound consisting of a benzene ring fused to a five-membered imide ring.
It is commonly used as a building block in the synthesis of various pharmaceutical and agrochemical compounds.
Phthalimides have a wide range of biological activities, including anti-inflammatory, analgesic, and antimicrobial properties.
Researchers often study phthalimide derivatives to explore their potential therapeutic applications.
This MeSH term provides a concise overview of the chemical structure and medicinal relevance of phthalimide, helping to guide reseach in this importnat area of organic and medicinal chemisry.

Most cited protocols related to «Phthalimide»

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Publication 2017
Acetic Acid Anions benzyl bromide Disulfides Ethers Mesylates phthalimide poly(ethylene glycol)-block-poly(propylene sulfide) Polymerization Polymers propylene sulfide Sulfhydryl Compounds thioacetic acid

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Publication 2008
Antibodies BLOOD Blood Vessel Clone Cells Cloning Vectors Drug Overdose Freezing Gelatins Glycoprotein Hormones, alpha Subunit Heparin Immunoglobulin G Integrins Intravital Microscopy Isoflurane isopentane ITGAM protein, human Left Ventricles Macrophage-1 Antigen Mus paraform Pentobarbital Polymers Radius Saline Solution Sodium Azide Sucrose Thoracic Cavity Tissues

Molecular mdelingThe chemical structures of inhibitors, shown in Table 1 were designed using Hyperchem software (version 7, Hypercube Inc.). Conformational analysis of the desired compounds was performed through Semi-empirical molecular orbital calculations (PM3) method using HYPERCHEM software. The molecular structures were optimized using Polak-Ribiere (conjugate gradient) algorithm until the root mean square (RMS) gradient was 0.01 kcal mol-1. Among all energy minima conformers, the global minimum of compounds were used in docking calculations and the resulted geometry was transferred into Autodock (version 4.2) program package, which was developed by Arthur J. Olson Chemometrics Group (12 (link)). The structure of docked N-phenyl substituent of phthalimide (1 (link)-16 (link)), N-[3-methyl-(2-pyridinyl)] phthalimide (19) and N-(3-amino-2-methylphenyl) succinimide (20) are shown in Table 1.
DockingDocking calculations were performed using Autodock software (version 4.2). A model of Na channel open pore was used as a receptor. This open pore model was developed based on homology model of the crystal structures of K channels (11 (link)). The model constructed by homology with potassium channel structures was reasonably successful in accounting for inner pore residue interactions with local anesthetics and anticonvulsant drugs like phenytoin. Desired compounds were docked into the active site as well as phenytoin which were acting as our reference drug and validation of our technique.
Docking was done using AutoDock4.2, in order to assign the perfect grid of each ligand, grid box values were obtained from trial and error and previous studies (13 (link)-15 (link)). Grid maps with 60×60×60 points were constructed and the grid point spacing was 0.375 Å (16 (link)). The implementing Lamarckian Genetic Algorithm (LGA), considered as one of the best docking methods available in AutoDock, was adopted to perform the molecular docking studies. The parameters for LGA were defined as follows: a maximum number of 250,000 energy evaluations; a maximum number of generations of 27,000; and mutation and crossover rates of 0.02 and 0.8, respectively. Pseudo-Solis & Wets parameters were used for local search, and 300 iterations of Solis & Wets local search were imposed. Both Autogrid and Autodock computations were performed on Cygwin and ten independent docking runs were performed for each phthalimide. Final docked conformations were clustered using a tolerance of 1 A ˚ root mean square deviation (RMSD) and the docking log (dlg) files were analyzed using the AutoDock Tools, graphical user interface of Autodock. The docked conformations of each ligand were ranked into clusters based on the binding energy and the top ranked conformations were visually analyzed. Hydrogen bonding and hydrophobic interactions between docked potent agents and macromolecule were analyzed using Auto Dock Tools (version1.50).
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Publication 2013
Anticonvulsants Hydrophobic Interactions Immune Tolerance inhibitors Ligands Local Anesthetics Microtubule-Associated Proteins Molecular Structure Mutation Pharmaceutical Preparations Phenytoin phthalimide Plant Roots Potassium Channel Reproduction Rumex Succinimides
Starting from 1-(2-aminoethyl)-piperazine (129 mg), yield =64.4%. 1H NMR (400 MHz, CDCl3), δ (ppm): 2.39–2.52 (m, 8H, piperazine), 2.60 (t, 2H, J = 6.7 Hz, phthalimide-CH2CH2N), 3.44 (s, 2H, NCH2Ph) 3.78 (t, 2H, J = 6.7 Hz, phtalimide–CH2CH2N), 7.19–7.27 (m, 5H, aromatics, Ph–CH2), 7.67–7.69 and 7.80–7.82 (m, 4H, phtalimide); m/z (ESI-MS): 350 (M + H)+.
Publication 2018
1H NMR phthalimide Piperazine
The compound 1 (200 mg, 0.69 mmol) was transferred into 50 mL flask, and it was added to 10 mL of dichloromethane. Then, a solution containing 20 mol% copper iodide (0.0268 g, according to alkyne-compound), azide-phthalimides 2a–c (1.2 equiv), and triethylamine (0.006 g~1 drop) was added. The mixture was stirred overnight (12 h) at r.t. (28°C) under argon atmosphere. A thin layer chromatography (TLC) was used to check the end of the reaction, using hexane : EtOAc (7 : 3) as the developing solvent system. The purification was performed by column chromatography on Merck silica gel 60 (70–230 mesh), using a system hexane : EtOAc (5 : 5). After the solvent evaporation, the product was crystallized in ethyl acetate.
4-(4,6-di-O-acetyl-2,3-dideoxy-<i>α</i>-D-erythro-hex-2-enopyranoside)-O-methyl-1-(2-phthalimidoethyl)-1,2,3-triazole (<bold>3a</bold>)

Yield: 90%. Solid. Mp 103–106°C. Rf = 0.40 (hexane : EtOAc, 3 : 7). [α]D25 + 63.3 (c 1, CH2Cl2); IR (KBr, cm−1): 3400, 3100, 2950, 1716, 1428, 1395, 1237, 1042, 718. 1H NMR (300 MHz, DMSO-d6): δ 2.02 (s, 3H, CH3CO), 2.06 (s, 3H, CH3CO), 3.94–4.03 (m, 3H, NCH2 and H-5), 4.11–4.16 (m, 2H, H-6 and H-6′), 4.56–4.70 (m, 4H, OCH2 and NCH2Phth), 5.09 (bs, 1H, H-1), 5.20 (dd, 1H, J = 9.6 and 1.5 Hz, H-4), 5.83–5.85 (m, 2H, H-2 and H-3), 7.84 (m, 4H, phthalimide), 8.18 (s, 1H, Htriazole). 13C NMR (75.5 MHz, CDCl3): δ 20.8, 20.9, 37.6, 47.9, 61.2, 62.0, 65.2, 66.9, 93.4, 123.6, 127.5, 129.4, 131.6, 134.3, 167.6, 170.3, 170.8. Anal. Calc. for C23H24N4O8: C, 57.02; H, 4.99; N, 11.56. Found: C, 57.29; H, 5.36; N, 11.42.

4-(4,6-di-O-acetyl-2,3-dideoxy-<i>α</i>-D-erythro-hex-2-enopyranoside)-O-methyl-1-(3-phthalimidopropyl)-1,2,3-triazole (<bold>3b</bold>)

Yield: 81%. Solid. Mp 125–127°C. Rf 0.40 (hexane : EtOAc, 3 : 7). [α]D25 + 49.6 (c 1, CH2Cl2); IR (KBr, cm−1): 3468, 2925, 2854, 1770, 1710, 1491, 1399, 1231, 1037, 722. 1H NMR (300 MHz, DMSO-d6): δ 2.03 (s, 3H, CH3CO), 2.05 (s, 3H, CH3CO), 2.18 (q, 2H, NCH2), 3.61 (t, 2H, J = 6.9 Hz, NCH2), 3.98 (ddd, 1H, J = 9.3, 5.1 and 3.0 Hz, H-5), 4.12–4.15 (m, 2H, H-6 and H-6′), 4.42 (t, 2H, J = 6.9 Hz), 4.59 (d, 1H, J = 12 Hz, OCHa), 4.72 (d, 1H, J = 12.3 Hz, OCHb), 5.17 (s, 1H, H-1), 5.20 (d, 1H, J = 9.6 Hz, H-4), 5.86 (bs, 2H, H-2 and H-3), 7.82–7.87 (m, 4H, phthalimides), 8.12 (s, 1H, Htriazole). 13C NMR (75.5 MHz, CDCl3): δ 20.8, 20.9, 29.4, 34.9, 47.2, 60.5, 62.8, 65.2, 67.0, 93.8, 122.0, 123.4, 127.5, 128.8, 129.5, 131.7, 134.3, 143.3, 168.3, 170.3, 170.9. Anal. Calc. for C24H26N4O8: C, 57.83; H, 5.26; N, 11.24. Found: C, 57.88; H, 5.46; N, 11.14.

4-(4,6-di-O-acetyl-2,3-dideoxy-<i>α</i>-D-erythro-hex-2-enopyranoside)-O-methyl-1-(4-phthalimidobutyl)-1,2,3-triazole (<bold>3c</bold>)

Yield: 68%. Solid. Mp 103–106°C. Rf 0.40 (hexane : EtOAc, 3 : 7). [α]D25 + 37.9 (c 1, CH2Cl2); IR (KBr, cm−1): 3464, 3141, 2935, 1769, 1711, 1437, 1398, 1370, 1230, 1038, 721. 1H NMR (400 MHz, DMSO-d6): δ 1.54–1.60 (q, 2H, CH2), 1.82–1.85 (q, 2H, CH2), 2.03 (s, 3H, CH3CO), 2.05 (s, 3H, CH3CO), 3.60 (t, 2H, J = 6.8 Hz, NCH2), 3.98 (ddd, 1H, J = 8.8, 5.2 and 3.2 Hz, H-5), 4.09–4.17 (m, 2H, H-6 and H-6′), 4.37 (t, 2H, J = 6.8 Hz), 4.60 (d, 1H, J = 12.4 Hz, OCHa), 4.72 (d, 1H, J = 12.4 Hz, OCHb), 5.17 (s, 1H, H-1), 5.20 (d, 1H, J = 9.6 Hz, H-4), 5.86 (bs, 2H, H-2 and H-3), 7.82–7.87 (m, 4H, phthalimides), 8.10 (s, 1H, Htriazole). 13C NMR (75.5 MHz, CDCl3): δ 20.8, 20.9, 25.5, 27.4, 29.6, 36.7, 49.4, 61.4, 62.7, 65.1, 66.9, 93.7, 122.7, 123.2, 127.4, 129.4, 131.8, 134.0, 144.0, 168.3, 170.2, 170.8. Anal. Calc. for C25H28N4O8: C, 58.59; H, 5.51; N, 10.93. Found: C, 58.47; H, 5.30; N, 10.56.

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Publication 2012

Most recents protocols related to «Phthalimide»

Specifically for the compound we moved forward with, ABP, synthesis followed techniques described previously [11 (link)] for two closely related compounds, N(3-trimethylaminopropyl)phenantridinium and 6-methoxy-N(3-aminopropyl)quilolinium. N(4-aminobutyl)phenantridinium (ABP) is a phenanthridine-based aminoalkyl moiety that is suitable for conjugation to dextran. Briefly, ABP was synthesized in a manner similar to N(3-trimethylaminopropyl)phenantridinium [11 (link)] by reflux of equimolar amounts of phenantridine and N(4-bromobutyl)phthalimide in acetonitrile overnight. A pale yellow–green precipitate was separated by filtration through Whatman-40 paper. From this intermediate phthalimide-protected compound, the phthalate group was removed by reflux in 6N HCl overnight and subsequent filtration, similar to procedures described for 6-methoxy-N(3-aminopropyl)quilolinium [11 (link)]. N(4-aminobutyl)phenantridinium (ABP) was twice recrystallized from hot 95% ethanol/5% deionized water and was stored as its chloride salt in a sealed glass vial protected from light until conjugation to glucose polymer (i.e., dextran).
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Publication 2024
A mixture of phthalimide 5 (1 mmol), hydroxybezaldehyde derivative 6 (1 mmol), and K2CO3 (1.3 mmol) in DMF (10 mL) was heated at 80 °C for 8 h. Upon completion of the following reaction, the mixture was poured into crushed ice, and the precipitate was filtered off and dried, affording aldehyde 7 [28 (link)].
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Publication 2024
The PAN fibers (cut into 50–80 mm with an average diameter of 21 μm) were commercially obtained from Toray Co., Ltd. (Tokyo, Japan). Ethylene glycol (98 wt%), guanidine carbonate (99 wt%), N-hydroxy phthalimide (98 wt%), anhydrous ethanol (95 wt%) and dipropyl sulfide (DPS) were purchased from Shanghai McLean Biochemical Technology Co., Ltd. (Shanghai, China), KOH (85 wt%) was purchased from Shanghai Runjie Chemical Reagent Co., Ltd. (Shanghai, China) Deionized water was self-made in the lab.
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Publication 2024
Phenylacetic acid (99.0%), zinc chloride (98.0%), phthalimide (98.0%), zinc phenylacetate (98.0%), α, ω-amino-terminated polyethylene glycol (PEG, Mw = 2 kDa, 99.5%), chloro (1,5-cyclooctadiene) iridium(I) dimer ([Ir(COD)2Cl2]2, 95.0%) and chlorosulphonic acid (97.0%)were obtained from J & K Chemical Ltd. Tirapazamine (TPZ), AQ4N, PR104, TH302 and solvents were purchased from Sigma-Aldrich Chemical Co. All the commercially available reagents were used as received without any further purification. The cell culture products were purchased from Thermo Fisher Scientific unless otherwise stated.
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Publication 2024

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Publication 2024

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Phthalimide is a chemical compound used in various applications, including as a building block in organic synthesis and as a pharmaceutical intermediate. It is a crystalline solid with a melting point of approximately 232 degrees Celsius. Phthalimide is soluble in organic solvents and has a range of chemical properties that make it useful in various laboratory and industrial processes.
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DMSO is a versatile organic solvent commonly used in laboratory settings. It has a high boiling point, low viscosity, and the ability to dissolve a wide range of polar and non-polar compounds. DMSO's core function is as a solvent, allowing for the effective dissolution and handling of various chemical substances during research and experimentation.
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Triethylamine is a clear, colorless liquid used as a laboratory reagent. It is a tertiary amine with the chemical formula (CH3CH2)3N. Triethylamine serves as a base and is commonly employed in organic synthesis reactions.
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Acetonitrile is a colorless, volatile, flammable liquid. It is a commonly used solvent in various analytical and chemical applications, including liquid chromatography, gas chromatography, and other laboratory procedures. Acetonitrile is known for its high polarity and ability to dissolve a wide range of organic compounds.
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Hydrazine monohydrate is a chemical compound with the formula N2H4·H2O. It is a colorless, crystalline solid with a distinctive ammonia-like odor. Hydrazine monohydrate is commonly used as a reducing agent, a fuel component, and in the manufacture of various chemicals and pharmaceuticals.
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Prism 6 is a data analysis and graphing software developed by GraphPad. It provides tools for curve fitting, statistical analysis, and data visualization.
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The Synergy H1 is a multi-mode microplate reader designed for a variety of applications. It is capable of absorbance, fluorescence, and luminescence detection.
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Bovine serum albumin (BSA) is a common laboratory reagent derived from bovine blood plasma. It is a protein that serves as a stabilizer and blocking agent in various biochemical and immunological applications. BSA is widely used to maintain the activity and solubility of enzymes, proteins, and other biomolecules in experimental settings.
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Phthalimide potassium salt is a chemical compound used as an intermediate in organic synthesis. It is a white, crystalline solid that is soluble in water and other polar solvents. The compound is commonly used in the preparation of various pharmaceutical and agrochemical products.
Sulfur is a naturally occurring element that is used in various laboratory applications. It is a yellow, solid substance that is insoluble in water but soluble in various organic solvents. Sulfur serves as a core component in many chemical reactions and processes conducted in laboratory settings.

More about "Phthalimide"

Phthalimide is a versatile heterocyclic organic compound that has gained significant attention in the fields of pharmaceutical and agrochemical research.
This five-membered imide ring fused to a benzene ring is commonly used as a building block in the synthesis of various bioactive compounds.
Phthalimides and their derivatives exhibit a wide range of biological activities, including anti-inflammatory, analgesic, and antimicrobial properties.
Researchers often explore the therapeutic potential of phthalimide-based compounds, investigating their effectiveness in treating various medical conditions.
In addition to phthalimide, other related compounds and solvents play important roles in the synthesis and study of these heterocyclic compounds.
DMSO (dimethyl sulfoxide) is a commonly used solvent in phthalimide research, known for its ability to dissolve a wide range of organic and inorganic compounds.
Triethylamine, another key reagent, is often employed as a base in organic reactions involving phthalimides.
Acetonitrile, a polar aprotic solvent, is also frequently utilized in the purification and analysis of phthalimide derivatives.
Hydrazine monohydrate, a reducing agent, can be used in the synthesis of phthalimide-based compounds.
Analytical techniques such as Prism 6 and Synergy H1 are often employed to characterize and evaluate the properties of phthalimide-based compounds.
Bovine serum albumin, a common protein used in biological assays, may also be utilized in the assessment of phthalimide's biological activities.
Furthermore, the phthalimide potassium salt and sulfur are important precursors and reagents in the synthesis of phthalimide-based molecules, contributing to the diverse chemistry and potential applications of this heterocyclic compound.