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Journal articles on the topic 'Phthalimide'

Author: Grafiati

Published: 4 June 2021

Last updated: 30 January 2023

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1

Zhao, Xue. "Synthesis and application of N-butyl substituted phthalimide disperse dyes." Textile Research Journal 89, no. 15 (October 11, 2018): 3034–47. http://dx.doi.org/10.1177/0040517518805380.

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Three azo dyes were synthesized using N-butyl substituted phthalimides as diazo components. All of the synthesized intermediate derivatives and dyes were characterized by mass spectrometry, proton nuclear magnetic resonance, infrared (IR) and elemental analyses. Synthesized dyes were also evaluated for their dyeing behavior and fastness properties toward polyester fabric. The ultraviolet-visible absorption maxima of the dyes were observed in the range of 445–563 nm. Bromo and cyano substitutions at the 3- and/or 5- positions of the phthalimide ring resulted in hypsochromic and bathochromic shifts, respectively. IR spectra peaks at 1770 and 1395 cm−1 of hydrolyzed dye showed that C–O groups appeared under relatively mild alkaline conditions. The K/ S values of dyed polyester/elastane fabrics decreased obviously as the pH value increased. Hydrolysis of the phthalimide ring was found to be largely influenced by steric effects rather than inductive effects. Bromo substituted dyes have the lowest rates of hydrolysis. Compared with S-type dyeing disperse dyes, phthalimide dyes have lower dyeing rates and lower levelness of dye migration. The ωB97XD/6-311G(d,p) calculation found that pi-stacking interactions of phthalimide–benzene and phthalimide–phthalimide dimers increased the dye–fiber and dye–dye interactions.

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2

Oksdath-Mansilla, Gabriela, Adrián A. Heredia, Juan E. Argüello, and Alicia B. Peñéñory. "Photochemistry of N-(selenoalkyl)-phthalimides. Formation of N, Se-heterocyclic systems." Photochemical & Photobiological Sciences 14, no. 4 (2015): 726–36. http://dx.doi.org/10.1039/c4pp00452c.

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A number of selenium heterocyclic derivatives are obtained upon direct or acetone-sensitized irradiation of a variety ofN-(selenomethyl)alkyl-phthalimides. The reaction proceeds by photoinduced intramolecular electron transfer between the Se atom and the phthalimide moiety.

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3

Gramage-Doria, Rafael, Yu-Chao Yuan, and Christian Bruneau. "Merging Transition-Metal Catalysis with Phthalimides: A New Entry to Useful Building Blocks." Synthesis 50, no. 21 (September 17, 2018): 4216–28. http://dx.doi.org/10.1055/s-0037-1610282.

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Phthalimides have found their main application in organic synthesis as protecting groups for primary amines during the multistep synthesis of biologically relevant targets. On the other hand, phthalimide functionalization is rather challenging and it is traditionally associated with the use of over-stoichiometric amounts of environmentally hazardous reagents. In this short review, we describe and discuss how, in the last decades, transition-metal catalysts have provided useful organic building blocks after selective transformation of the phthalimide skeleton in a more efficient and sustainable manner.1 Introduction2 Partial Carbonyl Reduction3 Full Carbonyl Reduction4 Aromatic Ring Reduction5 Five-Membered-Ring Opening6 Conclusion

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4

Basu, Souradeep, Alexander H. Sandtorv, and David R. Stuart. "Imide arylation with aryl(TMP)iodonium tosylates." Beilstein Journal of Organic Chemistry 14 (May 11, 2018): 1034–38. http://dx.doi.org/10.3762/bjoc.14.90.

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Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP)iodonium tosylate salts. The aryl transfer from the iodonium moiety occurs under electronic control with the electron-rich trimethoxyphenyl group acting as a competent dummy ligand. The yields of N-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups.

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5

Hasaninejad, Alireza, Abdolkarim Zare, Ahmad Reza Moosavi-Zare, Fatemeh Khedri, Rahimeh Rahimi, and Ali Khalafi-Nezhad. "Cs2CO3/[bmim]Br as an Efficient, Green, and Reusable Catalytic System for the Synthesis of N-Alkyl Derivatives of Phthalimide under Mild Conditions." Research Letters in Organic Chemistry 2008 (December 18, 2008): 1–4. http://dx.doi.org/10.1155/2008/419054.

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Aza-conjugate addition of phthalimide to α,β-unsaturated esters efficiently achieves in the presence of catalytic amount of Cs2CO3 and ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br) under mild reaction conditions (70°C) to afford N-alkyl phthalimides in high yields and relatively short reaction times.

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6

Le, Zhang Gao, Tao Zhong, Zong Bo Xie, and Jiang Ping Xu. "Solvent-Free N-Alkylation of Phthalimide Catalyzed by Basic Ionic Liquids." Advanced Materials Research 233-235 (May 2011): 1431–34. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.1431.

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Solvent-freeN-alkylation of phthalimide with alkyl halides catalyzed by basic ionic liquids was developed in this conmmunication. With a comparative study, [Bmim]OH (1-butyl-3-methyl imidazolium hydroxide) exhibited the highest catalytic activity among the selected basic ionic liquids, which afforded a convenient, efficient and general protocol forN-alkyl phthalimides exclusively.

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7

Luzzio, Frederick A., DeAnna Piatt Zacherl, and William D. Figg. "A facile scheme for phthalimide ⇌ phthalimidine conversion." Tetrahedron Letters 40, no. 11 (March 1999): 2087–90. http://dx.doi.org/10.1016/s0040-4039(99)00152-5.

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8

Aly, A. A., H. M. Ammar, and A. A. Khalil. "Copolymerization Parameters of 2-(N-Phthalimido) ethyl Methacrylate with Different Vinyl Monomers." Material Science Research India 8, no. 1 (June 25, 2011): 17–24. http://dx.doi.org/10.13005/msri/080103.

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2-(N-phthalimido)ethyl methacrylate was prepared by the reaction of methacrylic acid with N-(2-hydroxyethyl)phthalimide in presence of N,N?-dicyclohexylcarbodiimide. The monomer reactivity ratios for copolymerization reactions of 2-(N-phthalimido)ethyl methacrylate with methyl acrylate, ethyl acrylate, butyl acrylate and styrene, respectively, in solution with azobisisobutyronitrile (AIBN) as initiator, were estimated by nitrogen analysis. The structure of the copolymers was investigated by IR spectroscopy. The Q and e values for 2-(N-phthalimido)ethyl methacrylate were calculated. Some of the synthesized polymers were tested for their antimicrobial activity against bacteria and fungi.

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9

Jourdain, Isabelle, Michael Knorr, Tom Charenton, Carsten Strohmann, Jan-Lukas Kirchhoff, and Mohamed Othman. "(µ2-η4-N-(2-Butynyl)phthalimide)(hexacarbonyl)dicobalt." Molbank 2023, no. 1 (January 11, 2023): M1545. http://dx.doi.org/10.3390/m1545.

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The reaction of [Co2(CO)8] with an equimolar amount of the internal alkyne N-(2-butynyl)phthalimide (1-Phthalimido-2-butyne) 1 in heptane solution yields the title compound [Co2(CO)6(µ-phthalimidoCH2C≡CMe)] 2. Compound 2 has been characterized using IR, 1H and 13C NMR spectroscopy; the tetrahedrane-type cluster framework has been ascertained using a single-crystal X-ray diffraction study performed at 100 K.

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10

Perveen, Shagufta, and Raha Orfali. "L-Proline-Catalyzed Synthesis of Phthalimide Derivatives and Evaluation of Their Antioxidant, Anti-Inflammatory, and Lipoxygenase Inhibition Activities." Journal of Chemistry 2018 (August 1, 2018): 1–6. http://dx.doi.org/10.1155/2018/5198325.

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A study was planned to synthesize the phthalimide derivatives as phthalimides have versatile biological activities. To synthesize the phthalimide derivatives, initially the reaction was optimized with various catalysts, and L-proline was found to be the best catalyst as it provided excellent yield. A series of phthalimide derivatives was synthesized by facile one-top reaction of phthalic acid with aryl amines under mild reaction conditions in the presence of L-proline as catalyst. Products were obtained in excellent yields and structurally characterized by 1H, 13C NMR, and mass spectral data. Products 1–7 were evaluated for antioxidant, anti-inflammatory, and lipoxygenase enzyme inhibition activities. Compounds 1 and 4 showed potent antioxidant activity under DPPH with IC50 values 27.3 and 25.0 μM when compared with the standard BHA (IC50 = 44.2 μM), respectively. Compounds 1 and 4 further showed strong lipoxygenase inhibition activity with IC50 values 21.34 and 20.45 μM when compared with standard baicalein (IC50 = 22.60 μM), respectively. Compound 2 was found to be promising and about equal to the used standard aspirin in the inhibition of bovine serum albumin denaturation, while other compounds showed weak-to-moderate % inhibition.

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11

McClelland, Robert A., N. Esther Seaman, James M. Duff, and R. E. Branston. "Kinetics and equilibrium in the ammonolysis of substituted phthalimides." Canadian Journal of Chemistry 63, no. 1 (January 1, 1985): 121–28. http://dx.doi.org/10.1139/v85-020.

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Kinetic studies are reported for the base hydrolysis to phthalamic acid anions (H) and ammonolysis to phthalamides (A) for seven phthalimides (P): 1, unsubstituted; 2, 4-NO2; 3, 4-Cl; 4, 4-t Bu; 5, 3-NO2; 6, 3-Me; 7, 3-Me3Si. The hydrolysis kinetics require two mechanisms, one which is first order in neutral imide and first order in hydroxide ion, and a second, which is important only in quite concentrated NaOH, which is first order in neutral phthalimide and second order in hydroxide ion. Ammonolysis kinetics for 1–5 revealed the rate law: Rate = kN [Unionized phthalimide] [NH3][OH−]. A mechanism is proposed with rate-determining breakdown of the anionic form of the tetrahedral intermediate derived by addition of NH3 to the phthalimide. The ammonolysis is reversible. The phthalamide hydrolyzes to the phthalamic acid via cyclization to an intermediate phthalimide, which is detected in concentrated base where its formation from phthalamide is more rapid than its subsequent hydrolysis. Rate constants for the cyclization follow the rate law: Rate = kcyc [Phthalamide][OH−]. This reaction is the microscopic reverse of the ammonolysis, and the ratio kN/kcyc provides the equilibrium constant Keq for the reaction P + NH3 = A. Values for 1–5 lie in the range 2 × 102 – 4 × 103. With 3-methylphthalimide, kinetics in aqueous ammonia do not obey a first-order relationship, but they could be analyzed by a scheme whereby the phthalimide is converted reversibly to the phthalamide and simultaneously undergoes an irreversible hydrolysis. The value of Keq in the system is 1.8. With 3-trimethylsilylphthalimide the value of Keq is further reduced to 0.01. The ammonolysis reaction does occur more quickly than hydrolysis but the equilibrium is so unfavorable that even in concentrated ammonia only a small amount of the phthalamide is ever formed.

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12

Ahanj, Negin, Mehdi Taghavi, and Ayyub Mojaddami. "Evaluation of Cytotoxicity and Molecular Docking Studies of Phthalimide and Naphthalimide Derivatives as Potential Anticancer Agents." Jundishapur Journal of Medical Sciences 20, no. 4 (October 1, 2021): 366–75. http://dx.doi.org/10.32598/jsmj.20.4.2456.

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Background and Objectives Cancer is the second leading cause of death in the world after cardiovascular disease, so the aim of the present study was to investigate phthalimide and naphthalimide derivatives in order to develop anticancer compounds. Subjects and Methods In this study, the cytotoxic activity of six phthalimed and naphthalamide derivatives was evaluated using MTT method on three cancerous cell lines, including breast cancer (MCF-7), ovarian cancer (SKOV3) and lung cancer (A549) cell line. Molecular Docking studies were also performed to determine the binding energy and the compounds interaction with DNA as a possible target of these compounds. Results Based on MTT results, compound C1, a naphthalimide derivative, showed the highest cytotoxic activity. IC50 values of this compound against MCF-7, SKOV3 and A549 cancer cell lines were 1.7, 6.2 and 9.5 μM, respectively. Also, comparison of phthalimide and naphthalimide derivatives showed that compounds C1, C3, C5 with carboxyl group had better effects than other compounds, C2, C6, C4, which bearing 5-amidoisophthalic acid moiety. Conclusion In general, naphthalimide derivatives showed better cytotoxicity than phthalimide derivatives. Compound C1 has the highest cytotoxic activity on all three cancer cell lines and can be further studied in the development of new anti-cancer compounds.

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13

Luzzio, Frederick A., DeAnna Piatt Zacherl, and William D. Figg. "ChemInform Abstract: A Facile Scheme for Phthalimide ⇔ Phthalimidine Conversion." ChemInform 30, no. 25 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.199925058.

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14

Barbarossa, Alexia, Alessia Catalano, Jessica Ceramella, Alessia Carocci, Domenico Iacopetta, Camillo Rosano, Carlo Franchini, and Maria Stefania Sinicropi. "Simple Thalidomide Analogs in Melanoma: Synthesis and Biological Activity." Applied Sciences 11, no. 13 (June 23, 2021): 5823. http://dx.doi.org/10.3390/app11135823.

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Thalidomide is an old well-known drug that is still of clinical interest, despite its teratogenic activities, due to its antiangiogenic and immunomodulatory properties. Therefore, efforts to design safer and effective thalidomide analogs are continually ongoing. Research studies on thalidomide analogs have revealed that the phthalimide ring system is an essential pharmacophoric fragment; thus, many phthalimidic compounds have been synthesized and evaluated as anticancer drug candidates. In this study, a panel of selected in vitro assays, performed on a small series of phthalimide derivatives, allowed us to characterize compound 2k as a good anticancer agent, acting on A2058 melanoma cell line, which causes cell death by apoptosis due to its capability to inhibit tubulin polymerization. The obtained data were confirmed by in silico assays. No cytotoxic effects on normal cells have been detected for this compound that proves to be a valid candidate for further investigations to achieve new insights on possible mechanism of action of this class of compounds as anticancer drugs.

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15

Yang, Er-Qun, Jun-Tao Zhang, Xiao-Ping Cao, and Jin-Zhong Gu. "N-[2-(2-Hydroxyethoxy)phenethyl]phthalimide." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 5, 2012): o1636. http://dx.doi.org/10.1107/s1600536812018429.

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The title compound, C18H17NO4, was obtained accidentally through acid-catalysed aromatization of a phthalimide-substituted 2-(1-hydroxyethyl)cyclohex-2-enone. It exhibits an intramolecular O—H...Oc (c = carbonyl) hydrogen bond and forms a three-dimensional network structure via π–π stacking interactions between adjacent benzene rings (phthalimide-to-phenylene and phthalimide-to-phthalimide), with centroid–centroid distances of 3.8262 (6) and 3.6245 (5) Å.

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16

Nagel, N., H. Bock, and J. W. Bats. "Potassium Phthalimide." Acta Crystallographica Section C Crystal Structure Communications 52, no. 6 (June 15, 1996): 1344–46. http://dx.doi.org/10.1107/s0108270196002387.

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17

Orzeszko, A., R. Gralewska, B. J. Starościak, and Z. Kazimierczuk. "Synthesis and antimicrobial activity of new adamantane derivatives I." Acta Biochimica Polonica 47, no. 1 (March 31, 2000): 87–94. http://dx.doi.org/10.18388/abp.2000_4065.

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A series of fourteen derivatives of adamantane was synthesised. The new compound 4-(adamant-1-ylmethoxycarbonyl)phthalanhydride obtained from 1-adamantane-methanol and trimellitic anhydride chloride appeared very useful for preparation of a number of N-substituted phthalimides. Antimicrobial activity of the newly obtained derivatives such as, for example, 4-(adamant-1-ylmethoxycarbonyl)-N-(5-carboxypentamethylene)p hthalimide or 4-(adamant-1-ylmethoxycarbonyl)-N-(L-alanyl)phthalimide was tested against Staphylococcus aureus, Bacillus sp., Micrococcus flavus and Enterococcus faecium. The minimal inhibitory concentration (MIC) for these compounds against S. aureus were 0.022 and 0.05 microg/ml, respectively.

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18

Almeida, Marcel L., Maria C. V. A. Oliveira, Ivan R. Pitta, and Marina G. R. Pitta. "Advances in Synthesis and Medicinal Applications of Compounds Derived from Phthalimide." Current Organic Synthesis 17, no. 4 (July 27, 2020): 252–70. http://dx.doi.org/10.2174/1570179417666200325124712.

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Phthalimide derivatives have been presenting several promising biological activities in the literature, such as anti-inflammatory, analgesic, antitumor, antimicrobial and anticonvulsant. The most well-known and studied phthalimide derivative (isoindoline-1,3-dione) is thalidomide: this compound initially presented important sedative effects, but it is now known that thalidomide has effectiveness against a wide variety of diseases, including inflammation and cancer. This review approaches some of the recent and efficient chemical synthesis pathways to obtain phthalimide analogues and also presents a summary of the main biological activities of these derivatives found in the literature. Therefore, this review describes the chemical and therapeutic aspects of phthalimide derivatives.

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19

Assis, Shalom Pôrto de Oliveira, Moara Targino da Silva, Ronaldo Nascimento de Oliveira, and Vera Lúcia de Menezes Lima. "Synthesis and Anti-Inflammatory Activity of New Alkyl-Substituted Phthalimide 1H-1,2,3-Triazole Derivatives." Scientific World Journal 2012 (2012): 1–7. http://dx.doi.org/10.1100/2012/925925.

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Four new 1,2,3-triazole phthalimide derivatives with a potent anti-inflammatory activity have been synthesized in the good yields by the 1,3-dipolar cycloaddition reaction fromN-(azido-alkyl)phthalimides and terminal alkynes. The anti-inflammatory activity was determined by injecting carrageenan through the plantar tissue of the right hind paw of Swiss white mice to produce inflammation. All the compounds3a–cand5a–cexhibited an important anti-inflammatory activity; the best activity was found for the compounds3band5c, which showed to be able to decrease by 69% and 56.2% carrageenan-induced edema in mice. These compounds may also offer a future promise as a new anti-inflammatory agent.

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20

Miranda, Alexandre, Paula Marcos, José Ascenso, M. Robalo, Vasco Bonifácio, Mário Berberan-Santos, Neal Hickey, and Silvano Geremia. "Conventional vs. Microwave- or Mechanically-Assisted Synthesis of Dihomooxacalix[4]arene Phthalimides: NMR, X-ray and Photophysical Analysis." Molecules 26, no. 6 (March 10, 2021): 1503. http://dx.doi.org/10.3390/molecules26061503.

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Direct O-alkylation of p-tert-butyldihomooxacalix[4]arene (1) with N-(bromopropyl)- or N-(bromoethyl)phthalimides and K2CO3 in acetonitrile was conducted under conventional heating (reflux) and using microwave irradiation and ball milling methodologies. The reactions afforded mono- and mainly distal di-substituted derivatives in the cone conformation, in a total of eight compounds. They were isolated by column chromatography, and their conformations and the substitution patterns were established by NMR spectroscopy (1H, 13C, COSY and NOESY experiments). The X-ray structures of four dihomooxacalix[4]arene phthalimide derivatives (2a, 3a, 3b and 5a) are reported, as well as their photophysical properties. The microwave (MW)-assisted alkylations drastically reduced the reaction times (from days to less than 45 min) and produced higher yields of both 1,3-di-substituted phthalimides (3a and 6a) with higher selectivity. Ball milling did not reveal to be a good method for this kind of reaction.

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21

Keita, Hamidou. "Adamantane-Functionalized Phthalimide Scaffold: Pathways to Supramolecular Interactions and Drug Discovery." Organics 2, no. 4 (November 11, 2021): 388–94. http://dx.doi.org/10.3390/org2040022.

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Herein, the synthesis of a novel adamantanyl-functionalized phthalimide scaffold is demonstrated. The novel compound could be used as a precursor for various synthetic pathways owing to the generic use of adamantane substituents as the driving force for supramolecular interactions with macrocycles and N-substituted phthalimide derivatives as a core structure in numerous drugs. The adamantanyl-functionalized phthalimide scaffold contains bromide groups on the C4 and C5 positions of the benzene ring, effectively allowing further facile modifications of the scaffold. The structure was fully characterized including single-crystal X-ray crystallography. The crystal structure shows an adamantane moiety at an angle of 115.57(7)° to the phthalimide core, hence sterically freeing the adamantane unit for host–guest interactions.

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22

Listyani, Tiara Ajeng, and Rina Herowati. "Analisis Docking Molekuler Senyawa Derivat Phthalimide sebagai Inhibitor Non-Nukleosida HIV-1 Reverse Transcriptase." Jurnal Farmasi Indonesia 15, no. 2 (November 1, 2018): 123–34. http://dx.doi.org/10.31001/jfi.v15i2.445.

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Senyawa derivat phthalimide dilaporkan sebagai kelas baru inhibitor nonnukleosida reverse transcriptase. Analisis docking molekuler senyawa derivat phthalimide terhadap enzim reverse transcriptase diperlukan untuk mengetahui afinitas dan pola interaksi antara senyawa di atas dengan enzim reverse transcriptase. Senyawa derivat phthalimide dioptimasi geometri menggunakan perangkat lunak VegaZZ selanjutnya dilakukan dengan cara preparasi target, preparasi ligan, validasi metode docking, dan analisis docking menggunakan PyRx-Python 0.8 - AutoDock Vina sehingga didapatkan interaksi ligan dengan target, energi bebas pengikatan, ikatan hidrogen, dan pola interaksi. Pola interaksi dilihat dari tiga puluh tiga senyawa derivat phthalimide dengan enzim reverse transcriptase menunjukkan ikatan hidrogen dengan asam amino Lys101 dimana interaksi tersebut mirip dengan interaksi senyawa TIBO R 86183 yang merupakan ligan asli protein target.

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23

Jiang, Zhou, Jun-Dong Wang, Mei-Jin Lin, Nai-Sheng Chen, and Jin-Ling Huang. "2,2′-Methylenebis(isoindoline-1,3-dione)." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (October 24, 2007): o4385. http://dx.doi.org/10.1107/s1600536807050738.

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The title compound, C17H10N2O4, consists of two phthalimide units connected by a methylene bridge. The N—C—N bond angle is 110.64 (12)°. In the crystal structure, the dihedral angle between the two phthalimide units in one molecule is 88.96 (2)°. The crystal packing is stabilized by the π–π overlap of neighboring phthalimide units, with closest interplanar packing distances of 3.470 (1) and 3.626 (7) Å, and by weak C—H...O interactions.

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24

Journal, Baghdad Science. "Synthesis, Characterization and Antimicrobial Screening of New Schiff Bases Linked to Phthalimidyl Phenyl Sulfonate Moiety." Baghdad Science Journal 11, no. 2 (June 1, 2014): 438–46. http://dx.doi.org/10.21123/bsj.11.2.438-446.

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A series of Schiff bases linked to phthalimidyl phenyl sulfonate moiety have been synthesized via multistep synthesis. The first step involved reaction of phthalic anhydride with aniline producing N-phenyl phthalamic acid which was subsequently dehydrated to the corresponding N-phenyl phthalimide via treatment with acetic anhydride and anhydrous sodium acetate. The synthesized imide was treated with chlorosulfonic acid in the third step producing 4-(N-phthalimidyl) phenyl sulfonyl chloride which was introduced in reaction with 4-hydroxy acetophenone in the fourth step producing 4-[4-(N-phthalimidyl) phenyl sulfonate] acetophenone and this in turn was introduced successfully in condensation reaction with various aromatic primary amines affording the desired new Schiff bases. The newly synthesized compounds were characterized through spectral data including FTIR, 1HNMR and 13CNMR. Antimicrobial activity of the prepared Schiff bases was evaluated against two types of bacteria and one type of fungi and the new Schiff bases were found to exhibit good antimicrobial activity against the tested organisms.

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25

Brito, Iván, Danitza Vargas, Andrea Reyes, Alejandro Cárdenas, and Matías López-Rodríguez. "N-(Triphenylmethylsulfanyl)phthalimide." Acta Crystallographica Section C Crystal Structure Communications 61, no. 4 (March 11, 2005): o234—o236. http://dx.doi.org/10.1107/s0108270105004270.

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26

Steiner, T. "N-(Propargyloxy)phthalimide." Acta Crystallographica Section C Crystal Structure Communications 51, no. 6 (June 15, 1995): 1135–36. http://dx.doi.org/10.1107/s0108270194012941.

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27

Lv, Wei, Huijiao Liu, Wen Wang, E. Yang, Hongyu Zhen, and Qidan Ling. "Synthesis of new conjugated polymers with coordinated praseodymium complexes for polymer memory devices." RSC Advances 7, no. 30 (2017): 18384–91. http://dx.doi.org/10.1039/c6ra28757c.

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A series of novel praseodymium(Pr)-coordinated polymers with phthalimide moieties were synthesized. The effects of the phthalimide moiety and neutral Pr complex on the polymer memory device performance were investigated.

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28

Arenas, J. F., J. I. Marcos, and F. J. Ramírez. "Infrared and Raman Spectra of Phthalimide-15N-H and Phthalimide-15N-D." Applied Spectroscopy 43, no. 1 (January 1989): 118–22. http://dx.doi.org/10.1366/0003702894201987.

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A study of the infrared and Raman spectra of previously synthesized phthalimide-15N-H and phthalimide-15N-D has been carried out. With the new data obtained, the vibrational spectra of the phthalimide molecule in a C2 v* symmetry has been reassigned, but taking into account that the molecule in the solid state forms dimers bonded by intermolecular hydrogen bonds; these dimers have a Ci symmetry. On the other hand, a semi-empiric calculation of the force fields of this molecule has been carried out by the MINDO/3-FORCE method, which required a prior optimization of the molecular geometry; the force field was transformed to the space of internal coordinates.

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29

Banarouei, Nasimossadat, Asghar Davood, Hamed Shafaroodi, Ghazaleh Saeedi, and Abbas Shafiee. "N-arylmethylideneaminophthalimide: Design, Synthesis and Evaluation as Analgesic and Anti-inflammatory Agents." Mini-Reviews in Medicinal Chemistry 19, no. 8 (April 23, 2019): 679–87. http://dx.doi.org/10.2174/1389557518666180424101009.

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Background and Objective: N-aryl derivatives of phthalimide and 4-nitro phthalimide have demonstrated cyclooxygenase inhibitory activity. Also, they possess excellent analgesic and antiinflammatory activity. In this work, a new series of N-arylmethylideneamino derivatives of phthalimide and 4-nitro phthalimide were designed and synthesized. Methods: The designed compounds were synthesized by condensation of the appropriate aldehyde and N-aminophthalimide in ethanol at room temperature at PH around 3. Their analgesic and antiinflammatory activity were evaluated by acetic acid-induced pain test and carrageenan-induced paw edema test in mice and rats, respectively. Results and Conclusion:: The details of the synthesis and chemical characterization of the analogs are described. In vivo screening showed compounds 3a, 3b, 3f and 3h were the most potent analgesic compounds. In addition, compounds 3a, 3c, 3d, 3e and 3j indicated comparable anti-inflammatory activity to indomethacin as a reference drug.

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30

Gera, Ankur, Chander Mohan, and Sandeep Arora. "Synthesis of Phthaloylglycyl Hydrazide Derivatives: Selective Protection of Phthalimide Group from Hydrazinolysis." Current Organic Synthesis 15, no. 6 (August 29, 2018): 839–45. http://dx.doi.org/10.2174/1570179415666180601083256.

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Background: N-phthalimide amino acid hydrazide is a class of compounds that have the potential therapeutic use. In general, hydrazinolysis of N-substituted amino acid(s) ester removes the ester group and yields the corresponding hydrazide. However, in case if N-substitution group is phthalimide, phthalimide group is cleaved and not the ester group. The resulted compound, therefore, is amino acid ester rather than Nphthalimide amino acid hydrazide. The above class of compounds, because of susceptibility of phthalimide group to hydrazinolysis, has previously been synthesized by a lengthy three-step procedure. Objective: N-phthaloylglycyl hydrazide was synthesized by using new efficient, simplified, one step process. Hydrazone derivatives from substituted benzaldehydes, and substituted furaldehyde were also synthesized. Method: N-phthaloylglycyl hydrazide was synthesized from the corresponding carboxylic acid using 1-Ethyl- 3-(3-dimethylaminopropyl)carbodiimide (EDC) as a coupling agent and hydroxybenzotriazole (HOBt) as an activator. Hydrazone derivatives were synthesized by condensation of N-phthaloylglycyl hydrazide with substituted benzaldehyde/substituted furaldehydes. All the compounds were characterized by IR, 1H-NMR, 13CNMR, mass spectroscopy and elemental analysis. Results: The presence of EDC/HOBt resulted in hydrazinolysis of the carboxylic acid group and not the phthalimide group. N-phthaloylglycyl hydrazide was synthesized in good yield. Conclusion: We report the improved process of the synthesis of N-phthaloylglycyl hydrazide. This is the first report where stability of phthaloyl amino acid compound to hydrazine is demonstrated. The reaction may be explored for the reaction schemes where stability of phthalimide group to hydrazinolysis is required.

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31

Warzecha, Klaus-Dieter, Johann Lex, Jörg M. Neudörfl, and Axel G. Griesbeck. "N-(2-Phenethyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (March 29, 2006): o1580—o1581. http://dx.doi.org/10.1107/s1600536806010154.

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The molecule of the title compound, C16H13NO2, contains two planar units, viz. a phthalimide system and a phenyl ring in almost parallel orientation, linked by an ethylene bridge. In the crystal structure, the molecules form centrosymmetric pairs which are held together by π–π interactions between the phthalimide systems. The latter are stacked in a head-to-tail fashion with an interplanar distance of 3.263 (6) Å.

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32

Sato, Yasuhiko, Hideo Nakai, Masao Wada, Tomishige Mizoguchi, Yasumaru Hatanaka, Yoshihiro Migita, and Yuichi Kanaoka. "Photochemistry of the Phthalimide System, 37. Thiazacycloalkanols by Photocyclization ofS-SubstitutedN-(Thioalkyl)phthalimides." Liebigs Annalen der Chemie 1985, no. 6 (June 12, 1985): 1099–118. http://dx.doi.org/10.1002/jlac.198519850602.

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33

Cho, Dae Won, Patrick S. Mariano, and Ung Chan Yoon. "Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers." Beilstein Journal of Organic Chemistry 10 (February 27, 2014): 514–27. http://dx.doi.org/10.3762/bjoc.10.47.

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In this review, we describe direct and indirect photochemical approaches that have been developed for the preparation of phthalimide- and naphthalimide-based, lariat-type crown ethers. The direct route utilizes a strategy in which nitrogen-linked side chains containing polyethoxy-tethered phthalimides and naphthalimides, possessing terminal α-trialkylsilyl groups, are synthesized utilizing concise routes and UV-irradiation to form macrocyclic ring systems. In contrast, the indirect route developed for the synthesis of lariat-type crown ethers employs sequences in which SET-promoted macrocyclization reactions of α-trialkylsilyl-terminated, polyethoxy-tethered phthalimides and naphthalimides are followed by a side chain introduction through substitution reactions at the amidol centers in the macrocyclic ethers. The combined observations made in these investigations demonstrate the unique features of SET-promoted photocyclization reactions that make them well-suited for the use in the synthesis of functionalized crown ethers. In addition, while some limitations exist for the general use of SET-photochemical reactions in large-scale organic synthesis, important characteristics of the photoinduced macrocyclization reactions make them applicable to unique situations in which high temporal and spatial control is required.

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34

Bisht, Ajay Singh, and Rajat Bisht. "Microwave assested synthesis of phthalimide amino derivatives with their antioxidant potential." Current Trends in Pharmacy and Pharmaceutical Chemistry 3, no. 3 (July 15, 2021): 23–27. http://dx.doi.org/10.18231/j.ctppc.2021.007.

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Imide is the configuration of amide in which the nitrogen atom is affix to two carbonyl group. Imide mention to any compound which carry the divalent radical. Phthalimide possess a structural feature CHNO and an imide ring which help them to be biologically active and pharmaceutically useful.Phthalimides have served as starting materials and intermediates for the synthesis of many types of alkaloids and pharmacophores.In view of broad biological activity of phthalimide, we herein plan to synthesize a series of new phthalimide derivatives by incorporating new pharmacophores at various positions with the hope to get therapeutically active compounds. The aim the study is to synthesize phthalimide derivatives by using microwave assisted synthesis method and compare the activity of the synthesized molecules. Thus, the current communication employed the technology gracefully for the synthesis, identification and characterization of some novel derivatives by the reaction of Phthalic anhydride with urea, glycine, aniline, sulphanilic acid to yield various Phthalimide derivatives using domestic microwave by getting percentage yield 70.7%, 76.65%, 80.21% and 73.78% of synthesized compound BBBand Brespectively. The compound B(92.86%) showed higher percentage practical yield. All synthesized compound(s) were subjected to melting point determination, TLC analysis, column chromatography (for purification), H-NMR and Mass Spectrometry. All synthesized derivatives were subjected for DDPH scavenging activity, in which compound Bwas found to have high anti-oxidant potential (69.56%) when ascorbic acid was taken as standard. All the chemicals used were of highly pure and procured from Central Drug House (New Delhi).

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35

Huang, Peng-Mian, and Dao-Wu Yang. "N-(2,6-Dichlorobenzyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 14, 2007): o1251—o1252. http://dx.doi.org/10.1107/s1600536807006411.

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36

Lo, Kong Mun, and Seik Weng Ng. "N-(3-Bromophenyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 60, no. 5 (April 24, 2004): o848—o849. http://dx.doi.org/10.1107/s1600536804009547.

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37

Kauffmann, Brice, Claude Didierjean, Nicolas Brosse, Brigitte Jamart-Grégoire, and André Aubry. "N-(tert-Butyloxycarbonylamino)phthalimide." Acta Crystallographica Section E Structure Reports Online 60, no. 6 (May 8, 2004): o934—o935. http://dx.doi.org/10.1107/s1600536804010098.

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38

Sim, Yoke Ling, Azhar Ariffin, Mohammad Niyaz Khan, and Seik Weng Ng. "N-(2-Methoxyphenyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 65, no. 9 (August 22, 2009): o2218. http://dx.doi.org/10.1107/s1600536809032826.

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39

Sim, Yoke Ling, Azhar Ariffin, Mohammad Niyaz Khan, and Seik Weng Ng. "N-(4-Methoxyphenyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 65, no. 9 (August 22, 2009): o2219. http://dx.doi.org/10.1107/s1600536809032838.

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40

Fan, Yen May, Norzalida Zakaria, Azhar Ariffin, and Seik Weng Ng. "N-(2-Ethylphenyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 64, no. 9 (August 6, 2008): o1699. http://dx.doi.org/10.1107/s1600536808020448.

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41

Lynch, Daniel E., and Ian McClenaghan. "N-(8-Quinolylamino)phthalimide." Acta Crystallographica Section E Structure Reports Online 57, no. 1 (December 1, 2000): o16—o17. http://dx.doi.org/10.1107/s1600536800018109.

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The structure of the title compound, C17H11N3O2, (I), comprises twisted molecules that associateviaa single N—H...O intermolecular interaction, forming a linear one-dimensional hydrogen-bonded chain. The dihedral angle between the two ring systems is 89.9 (1)°.

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42

Chen, Ping, Ling Zhang, and Dan Li. "N-(4-Bromobenzyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (August 9, 2006): o3691—o3692. http://dx.doi.org/10.1107/s1600536806029552.

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43

Chen, Ping, Dan Li, and Ling Zhang. "N-(4-Chlorobenzyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (August 25, 2006): o4136—o4137. http://dx.doi.org/10.1107/s1600536806031266.

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44

Chen, Ping, Ling Zhang, and Dan Li. "N-(4-Methylbenzyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 62, no. 9 (August 31, 2006): o4188—o4189. http://dx.doi.org/10.1107/s1600536806033812.

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45

Garduño-Beltrán, Olga, Perla Román-Bravo, Felipe Medrano, and Hugo Tlahuext. "N-(2-Pyridylmethyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 65, no. 10 (September 30, 2009): o2581. http://dx.doi.org/10.1107/s160053680903846x.

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46

Sim, Yoke Leng, Azhar Ariffin, and Seik Weng Ng. "N-(2-Methoxyethyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 64, no. 6 (May 10, 2008): o1058. http://dx.doi.org/10.1107/s1600536808013548.

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47

Wu, Jing-Yun, Michael Yen-Nan Chiang, and Wen-Feng Zeng. "N-(2-Bromophenyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 58, no. 12 (November 15, 2002): o1370—o1371. http://dx.doi.org/10.1107/s1600536802020263.

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48

Bocelli, G., A. Cantoni, and P. Cozzini. "N-(p-Tolyl)phthalimide." Acta Crystallographica Section C Crystal Structure Communications 51, no. 11 (November 15, 1995): 2372–74. http://dx.doi.org/10.1107/s0108270195007177.

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49

Yazıcı, Serap, Nalan Türköz, Halil Kütük, Ismet Şenel, and Orhan Büyükgüngör. "N-(p-Methoxyphenylsulfanyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 63, no. 2 (January 24, 2007): o813—o814. http://dx.doi.org/10.1107/s1600536807002541.

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50

Xu, Dan, Yu-Quan Shi, Bin Chen, Yu-Hong Cheng, and Xu Gao. "N-(2-Fluorophenyl)phthalimide." Acta Crystallographica Section E Structure Reports Online 62, no. 2 (January 7, 2006): o408—o409. http://dx.doi.org/10.1107/s1600536805041206.

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