2,4,6-Trichloro-1,3,5-triazine/dimethylformamide as an efficient reagent for one-pot conversion of alcohols into N-alkylphthalimides

An efficient and mild method for the direct conversion of alcohols into N-alkylphthalimides using 2,4,6-trichloro-1,3,5-triazine and dimethylformamide was described.The reaction was preceded via(alcoxymethylene) dimethylammonium chloride intermediate and produced corresponding N-alkylphthalimides in good-to-excellent yields.

Synthesis and reversal effect of a novel N-substituted phthalimidesugar on doxorubicin resistant of human breast cancer cells

Thalidomide （α-N-phthalimido-glutarimide, TLD） is a kind of anti-angiogenic and anti-inflammatory drug, and showed effects in the treatment of several disease entities. In this study, the biological effects of a novel N-sugar substituted phthalimide （STA-35） on the regulation of multidrug resistance （MDR） to doxorubicin （ADR） were investigated. The proliferation of cancer cells was detected by a SRB assay. The activity of P-glycoprotein （P-gp） was determined by a Flow cytometry. The expression of P-gp was measured by western blotting. The results showed that STA-35 inhibited the proliferation of human breast cancer cell line MCF-7 and its ADR resistant cell line MCF-7/ADR, and the relative resistance was only 1.19. Meanwhile, STA-35 could sensitize the cytotoxicity of ADR in MCF-7/ADR cells. In addition, we found that STA-35 reduced the activity of P-gp by suppressing the P-gp expression, which was indicated by the increase in the accumulation of rhodamine 123 in MCF-7/ADR cells. These results suggested a promising application of STA-35 as the MDR reversing agent. The underlying mechanism of the effects might be attributed to the inhibition of P-gp.

Synthesis and cytotoxic activity of heterocycle-substituted phthalimide derivatives

A series of heterocycle-substituted phthalimide derivatives were synthesized.Structurally diverse derivatives with heterocyclic rings,including furan,imidazo[1,2-a]pyridine,1,3,4-thiadiazine,imidazo[2,1-b][1,3,4]thiadiazine,pyrazole,1,2,4-triazolo[3,4- b][1,3,4]thiadiazine,thiazole and thiazoline,were obtained by the reactions ofα-bromoketone intermediate with various nucleophiles containing oxygen,nitrogen and sulfur atom.Their cytotoxic activity was also evaluated against five human cancer cell lines in vitro.

PHOTO-CIDNP STUDIES OF PHTHALIMIDE DERIVATIVES IN THE PRESENCE OF TRIETHYLAMINE

The photoreactivity of some phthalimides was tested by CIDNP studies on the reactions with triethylamine.

An Unusual Reductive Ring-opening Reaction of Phthalimide with Sodium Hydride in DMF

An unusual reductive ring-opening reaction of phthalimide with sodium hydride in anhydrous DMF was observed for the first time. The presumed mechanism was described in detail.

Fragmentation of Some Substituted Phthalimides on Electron Impact Ionization

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Ionic liquid [bmim][BF_4] acts as solvent and promoter for synthesis of halo-containing N-arylphthalimides

A new synthetic process of N-arylphthalimide and halo-containing N-arylphthalimides through the reaction between phthalic anhydride and aromatic amines bearing halo groups in [bmim][BF4] was described, ionic liquid [bmim][BF4] acted as the dual role of solvent and promoter.

The Synthesis of Arylsulfonylphthalimides and Their Reactions with Several Amines in Acetonitrile

In this study, several N-(p-substituted-arylsulfonyl)phthalimides (1a-e) were synthesized. The synthesized compounds were then examined with respect to their substitution reactions with t-butylamine, diethylamine, cyclohexylamine, and trans-1,2-diaminocyclohexane in acetonitrile. In order to determine the mechanism, substituent effect, activation entropy, and nucleophile effect were used as criteria.

Synthesis, Characterization and Antiepileptic Activity of Some New N-Substituted Phthalimide Analogs

The present study was designed to investigate the anticonvulsant effect of series phthalimides possessing an N-aromatic amines moiety substituted at position 2 （2-7）. The compounds synthesized using phthalic anhydride and various amines in reflux synthesizer. The chemical structures of the titled compound were confirmed by physical and spectra analysis. All the synthesized compounds were evaluated in vivo for antiepileptic activity by using standard experimental models. Compounds： 2-（3H-1, 2, 4-Triazole-3-y） isoindoline-1, 3-dione （2）, Ethyl-4（1, 3-dioxoisoindoline-2-yl） benzoate 3 and 2-（4-nitrophenyl） isoindoline-1,3dione （7） were found significantly （P 〈 0.01-0.00001） delayed the onset and antagonized picrotoxin-induced seizures.

Synthesis, Spectral Characterization and Ligation of <i>N</i>-[2-(Phenylseleno)ethyl]phthalimide

PhSe-Na+ generated in situ by reduction of PhSeSePh, with sodium borohydride on reaction with N-(2-bromoethyl) phthalimide in N2 atmosphere results in the formation of N-[2-(phenylseleno)ethyl]phthalimide (L1). The title compound has been characterized by elemental analysis, FT-IR, 1H and 13C NMR techniques. The crystal structure of L1 has been solved by direct methods and refined by full-matrix least squares. The ligand L1 crystallize in the monoclinic space group. Selenium forms two Se-C linkages, one is due to Se-Calkyl and the other one to Se-Caryl. Further, the ligation reaction of L1 with complex 1 is also explored whose identities are characterized by spectroscopic techniques.

Photoinduced generation of alkyl and phthalimide nitrogen radicals from N-hydroxyphthalimide esters for the synthesis of benzophenone-type bioisosteres

N-Hydroxyphthalimide(NHPI)esters have emerged as powerful sources of alkyl radicals generated by single-electron transfer,but homolysis of NHPI ester to produce an alkyl radical and a phthalimide nitrogen radical is still in its infancy.In this study,we developed a light-induced method for generation of alkyl and phthalimide nitrogen radicals from NHPI esters and subsequent reactions of the radicals with[1.1.1]propellane and aryl aldehydes for rapid generation of bicycle[1.1.1]pentane ketones.This method does not require metals or photosensitizers,features a broad substrate scope(90 examples)and excellent functional group tolerance,and can be used for the functionalization of structurally complex natural products and drugs.Mechanistic investigations indicate that the reaction involves photoinduced homolytic cleavage of the Cs_(2)CO_(3)-NHPI ester complex to produce alkyl and phthalimide nitrogen radicals and subsequent hydrogen atom transfer between the phthalimide nitrogen radical and the aldehyde to generate an acyl radical.

Chlorinated phthalimide polymer donor as ultra-wide bandgap and deep HOMO guest for achieving highly efficient polymer solar cells

Quaternary approach has been receiving more and more attention due to its effectiveness in improving solar cell performance, while synthesis/selection of the fourth component is yet a key issue. Herein, we report a chlorinated phthalimide based donor polymer(namely Ph I-Cl) having an ultra-wide bandgap(2.10 e V) and a deep HOMO(-5.58 e V) level. Addition of Ph I-Cl as the third component of PM6:Y6 and the fourth of PM6:Y6:PC71BM increases both hole and electron mobilities and gives rise to more balanced charge carriers mobilities. Both the short-circuit current-density and fill-factor are increased and open-circuit voltage is well maintained, delivering 17.0% and 18.1% efficiencies, respectively. These results demonstrate that chlorination on the side thiophene of phthalimide-based donor polymer is a way to make deep HOMO and ultra-wide bandgap donor polymer guest used for highly efficient ternary and quaternary strategies.

Photoredox Synthesis of Thio-Functionalized Cyclic Ethers Using N-Sulfenyl Phthalimides as a Thiyl-Radical Precursor

Comprehensive Summary A visible-light mediated exclusively regioselective synthesis of 2,2-disubstituted thio-functionalized tetrahydrofurans,tetrahydro-pyrans and oxepanes has been described through an operationally simple and mild photoredox protocol.Thiyl radical generated from N-phenylsulfenyl phthalimide by photoredox catalysis was proven to be the key reactive intermediate in this reaction.

Phthalimide and Naphthalimide end-Capped Diketopyrrolopyrrole for Organic Photovoltaic Applications

Two small molecules named PI-DPP and NI-DPP with a DPP core as the central strong acceptor unit and phthalimide/naphthalimide as the terminal weak acceptor were designed and synthesized. The effects of terminal phthalimide/naphthalimide units on the thermal behavior, optical and electrochemical properties, as well as the photovoltaic performance of these two materials were systematically studied. Cyclic voltammetry revealed that the lowest unoccupied molecular orbitals （LUMO） （- -3.6 eV） of both molecules were intermediate to common electron donor （P3HT） and acceptor （PCBM）. This indicated that PI-DPP and NI-DPP may uniquely serve as electron donor when blended with PCBM, and as electron acceptor when blended with P3HT, where sufficient driving forces between DPPs and PCBM, as well as between P3HT and DPPs should be created for exciton dissociation. Using as electron donor materials, PI-DPP and NI-DPP devices exhibited low power conversion efficiencies （PCEs） of 0.90% and 0.76% by blending with PCBM, respectively. And a preliminary evaluation of the potential of the NI-DPP as electron acceptor material was carried out using P3HT as a donor material, and P3HT：NI-DPP device showed a PCE of 0.6%, with an open circuit voltage （Voc） of 0.7 V, a short circuit current density （Jsc） of 1.91 mA·cm^-2, and a fill factor （FF） of 45%.

Potassium phthalimide:An efficient and green organocatalyst for the synthesis of 4-aryl-7-(arylmethylene)-3,4,6,7-tetrahydro-1Hcyclopenta[d]pyrimidin-2(5H)-ones/thiones under solvent-free conditions

An efficient synthesis of Biginelli-type compounds using potassium phthalimide as a green, mild, and commercially available organocatalyst in a one-pot, multi-component cyclocondensation reaction of cyclopentanone, aldehydes, and urea/thiourea is reported. The present methodology is a green approach to access 4-aryl-7-（aryImethylene）-3,4,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-2（5H）-ones/thiones. It offers several merits such as simple operational procedures, no use of hazardous organic solvents, and cheap and environmentally friendly solid basic catalyst.

Tunable System for Electrochemical Reduction of Ketones and Phthalimides

Herein,we report an efficient,tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants.By utilizing NaN_(3) as the electrolyte and graphite felt as both the cathode and the anode,we were able to selectively reduce the carbonyl groups of the substrates to alcohols,pinacols,or methylene groups by judiciously choosing the solvent and an acidic additive.The reaction conditions were compatible with a diverse array of functional groups,and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds.Mechanistic studies showed that the reactions involved electron,proton,and hydrogen atom transfers.Importantly,an N_(3)/HN_(3) cycle operated as a hydrogen atom shuttle,which was critical for reduction of the carbonyl groups to methylene groups.

Water-Promoted Ring-Opening Reactions of N-Substituted Saccharins and Phthalimides by Amines

The reactions of N-substituted saccharins and phthalimides with amines were promoted by water.Various o-sulfamoyl benzamides and N,N′-disubstituted phthalamides were prepared in moderate to good yields.These reactions have prominent advantages,such as short reaction time,less by-products and simple isolation of the products.Water can probably stabilize the reaction intermediates and facilitate precipitation of the ring-opening products.When steric hindrance arose,hydrolytic compounds,either free acid or salts of the acids,were obtained.Possible reason for the formation of amine salts of o-sulfamoyl benzoic acids was proposed.

Enantioselective Organocatalytic Aza-Michael Additions of Phthalimide Derivatives to α,β-Unsaturated Aldehydes

Phthalimide derivatives as nitrogen nucleophiles with α,β-unsaturated aldehydes for asymmetric aza-Michael additions have been reported. The reactions proceed smoothly to afford corresponding Michael adducts in good yields （up to 98%） and enantioselectivities （up to 95% ee）.

Synthesis and in vitro Fungicidal Activity of a Series of Novel N-（Heterocycly）phthalimides

A series of novel phthalimides was prepared and tested for antifungal activity in vitro against seven phytopa- thogenic fungi： Rhizoctonia solani, Fusarium oxysporum f.sp. cucumerinum Owen., Botrytis cinerea, Fulvia fulva, Sclerotinia sclerotiorum de Bary, Phytophthora capsici, Botryosphaeria berengeriama. The results showed that those compounds holding the structure of 6-methylpyridin-2-yl exhibited good activity against Phytophthora capsici and Botrytis cinerea.

Synthesis,biochemical evaluation and computational simulations of new cytochrome bc1 complex inhibitors based on N-(4-aryloxyphenyl)phthalimides

The cytochrome bc1complex(the bc1complex or complex Ⅲ) is an attractive target for the discovery of numerous pharmaceuticals and pesticides. In order to identify new lead structures for this target, a new series of molecules, N-(4-aryloxyphenyl)phthalimides, were designed and synthesized in a straightforward manner. Our design strategy was to introduce a 4-aryloxyphenyl group, a fragment which exhibited promising bc1complex-inhibiting properties, into the aryl group of the valuable N-arylphthalimide backbone. Afterward, the biochemical evaluation of the newly synthesized compounds was carried out,and the results implied that several compounds demonstrated good activities against succinatecytochrome reductase(SCR, a mixture of mitochondrial complex Ⅱ and the bc1complex). Further studies confirmed that 3e’, a representative compound in this paper, was identified as an inhibitor of the bc1complex. Furthermore, computational simulations were also performed to better understand binding of 3e’ to the enzyme complex, which indicated that 3e’ should bind to the Qosite of the bc1complex.Consequently, we harbor the idea that this paper can provide a solid platform for synthesis and discovery of other bc1complex inhibitors.