Imide Derivatives Research Articles

Synthesis, characterization of amic acids and cyclic imides derived from acriflavine and evaluation of their antibacterial and antioxidant activity

Amic acids derivatives ( 1 – 4 ) have been synthesized by reaction of acriflavine with some cyclic anhydrides (succinic, maleic, phthalic and naphthalic) in absolute ethanol. Cyclic imides derivatives ( 5 – 8 ) were prepared by cyclization of amic acid derivatives using anhydrous acetic acid and anhydrase sodium acetate. The structures of the synthesized compounds have been identified by using the physical and spectral methods such as FT-IR, 1 H NMR and GC-Mass. The antibacterial activity of the prepared compounds was tested against ( staphylococs aureus and pseudomonas aeruginosa ) and all compounds show moderate to good antibacterial activity. However, the maximum inhibition zone was 15 mm against staphylococs aureus and 18 mm against pseudomonas aeruginosa . Furthermore, the antioxidant activity of these compounds have showed high activity and the maximum antioxidant was recorded to be 0.789 using the concentration 200 µg/cm 3 .

New promising halogenated cyclic imides derivatives as potential corrosion inhibitors for carbon steel in hydrochloric acid solution

In this paper, five new halogenated cyclic imides (1–5) were synthesized with a majority of methanoisoindole-1,3-dione unit through the addition/cyclization reaction of chlorendic anhydride (S1) with a different number of amines. The chemical structures of these new molecules were confirmed by FT-IR (Fourier-Transformed Infrared), 1H NMR, 13C NMR (Nuclear Magnetic Resonance) and Mass spectroscopies. Their performance as corrosion inhibitors, with varying chemical structure, was explored in reducing the corrosion rate of C-steel immersed in 0.5 M HCl solution at different exposure temperatures (25–55 °C) and different concentrations using various types of experimental and theoretical methods such as weight loss, electrochemical, spectroscopic, quantum chemical calculations and molecular dynamic simulations methods. The results indicate the inhibition performance (%IE) of all studied molecules increased with increasing concentration of inhibitors and decreasing solution temperatures. The weight loss method designated that compound 1 showed the best protection productivity of up to 89.6% for carbon steel at 29 × 10−6 M in 0.5 M HCl solutions at 25 °C. The presence of these compounds as inhibitors in the solution increases the charge transfer resistance and reduces the capacity of the double layer. Adsorption of these inhibitors molecules on the C-steel surface obeys the Langmuir adsorption isotherm and acts as mixed-type inhibitors. The results obtained confirm that the theoretical studies are in close agreement with the experimental observations.

Synthesis and Antiproliferative Activity of Chalcone-Imide Derivatives Based on 3,4-Dichloro-1H-Pyrrole-2,5-dione

A series of chalcone imide derivatives, 4'-aminochalcones-based dichloromaleimides, was synthesized from the reaction of 1-(4-acetylphenyl)-3,4-dichloro-1H-pyrrole-2,5-dione with various substituted aldehydes, or by treating 4'-aminochalcone with 3,4-dichlorofuran-2,5-dione in an alternative path. The structures of chalcone imide derivatives were established using IR, 1H NMR, 13C NMR, and mass spectroscopy. Antiproliferative effects of the newly synthesized compounds have been screened on two human cancer types via the MTT assay. Compounds with p-tolyl-1H-pyrrole-2,5-dione, and 4-bromophenyl-1H-pyrrole-2,5-dione derivatives, are highly active on the human liver cancer (HepG-2). On the other hand, all compounds were found to be more effective against breast cancer cells (MCF-7) than the positive control doxorubicin. The results of this work provide a basis for further research of selected chalcone-imide moiety as antiproliferative agents.

Synthesis, evaluation, molecular dynamics simulation and targets identification of novel pyrazole-containing imide derivatives

A new series of novel pyrazole-containing imide derivatives were synthesized and evaluated for their anticancer activities against A-549, Bel7402, and HCT-8 cell lines. Among these compounds A2, A4, A11 and A14 possessed high inhibition activity against A-549 cell lines with IC50 values at 4.91, 3.22, 27.43 and 18.14 μM, respectively, better than that of 5-fluorouracil (IC50=59.27 μM). A2, A4, and A11 also exhibited significant inhibitory activity towards HCT-8 and Bel7402 cell lines. Interestingly, the Heat Shock Protein 90α (Hsp90α, PDB ID: 1UYK) was found to be the potential drug target of these synthesized compounds with the aid of PharmMapper server (http://lilab.ecust.edu.cn/pharmmapper/) and docking module of Schrödinger (Maestro 10.2). Additionally, molecular dynamics simulation was performed out to explore the most likely binding mode of compound A2 with Hsp90α. Communicated by Ramaswamy H. Sarma

Human Serum Albumin-Occupying-Based Fluorescence Turn-On Analysis of Antiepileptic Drug Tiagabine Hydrochloride.

Tiagabine hydrochloride (TGB) is a clinically frequently used drug for anticonvulsion and reducing epileptic frequency. Over administration of TGB could bring about adverse effects, such as speech disorder, depression, and even suicidal tendencies. Therefore, accessible and sensitive assay for analysis of TGB becomes an urgent need toward guiding clinical medication. Here, we present the first report on fluorescence turn-on detection of TGB in urine testing. In this protocol, a fluorescent dye, perylene tetracarboxylic acid imide derivative (PTAI), is found specifically occupying the Sudlow site II of human serum albumin (HSA) and displays a new phenomenon of binding-induced quenching (BIQ). In presence of TGB, competitive binding of the TGB to the site II of HSA will trigger release of PTAI, thus successfully lighting up the fluorescence of PTAI. This label-free assay enjoys a broader working range (1-350 μM) and lower detection limit (0.218 μM) than the traditional liquid chromatography method and is uninterfered by the miscellaneous in the artificial urine. The BIQ probe highlights the merits of HSA as a quencher and a molecular recognition unit, and it opens up a way for studying drug-HSA interaction mechanism and noninvasive pharmaceutical testing.

N-Alkylation of N-trimethylsilyl derivatives of lactams, amides, and imides with alkyl sulfonates

The reaction of N-trimethylsilyl derivatives of amides and imides with alkyl sulfonates on heating affords the corresponding N-alkyl derivatives and trimethylsilyl sulfonates.

Theoretical and experimental investigation on the intersystem crossing kinetics in benzothioxanthene imide luminophores, and their dependence on substituent effects.

In spite of their remarkable luminescence properties, benzothioxanthene imide (BTXI, an imide containing rylene chromophores) derivatives have been largely overlooked compared to their perylene bisimide and naphthalene bisimide counterparts. Thus, their detailed photophysics are much less understood. In this paper, we show how relatively simple structural modifications of the backbone of BTXIs can lead to impressive variations in their inter-system crossing kinetics. Thus, through rational engineering of their structure, it is possible to obtain a triplet formation quantum yield that reaches unity, making BTXI a promising class of compounds for triplet-based applications (photodynamic therapy, electroluminescence, etc.).

Synthesis and biological evaluation of new chloro/acetoxy substituted isoindole analogues as new tyrosine kinase inhibitors.

We have developed a versatile synthetic approach for the synthesis of new isoindole derivatives via the cleavage of ethers from tricyclic imide skeleton compounds. An exo-cycloadduct prepared from the Diels-Alder reaction of furan and maleic anhydride furnished imide derivatives. The epoxide ring was opened with Ac2O or Ac2O/AcCl in the presence of a catalytic amount of H2SO4 in order to yield new isoindole derivatives 8a-d and 9a-d. The anticancer activity of these compounds was evaluated against the HeLa cell lines. The synthesized compounds showed inhibitory effects on the viability of HeLa cells and the degree of cytotoxicity was increased with the level of bigger branched isoindole derivatives. To better understand the acting mechanism of these molecules, western blot analysis was performed with using mTOR and its downstream substrates. In addition, human mTOR and ribozomal S6 kinase β1 (RS6Kβ1) have been investigated with molecular modelling studies as possible targets for compound series 8 and 9.

Direct C-H Bond Imidation with Benzoyl Peroxide as a Mild Oxidant and a Reagent.

A simple and mild Cu-catalyzed oxidative three-component oxidative Ugi-type method for the synthesis of a variety of substituted imides has been developed. In this direct imidation approach, benzoyl peroxide serves as both the oxidant and the carboxylate source, allowing not only the functionalization of C(sp3)-H bonds in α-position to an amine but also benzylic substrates. This procedure presents a wide substrate-type and functional group tolerance. Moreover, the mildness of the method permitted us to extend its application to the late stage functionalization of complex natural products such as the alkaloids brucine and strychnine, leading to interesting highly functionalized imide derivatives. On the basis of experimental and computational studies, a plausible mechanism has been proposed.

Metal selectivity for in-situ dehydrogenative cross-coupling of 2-hydroxymethylpyridine with small cyano anion

The synthesis, characterizations and crystal structures for [Cu(ipnm)(hmpH)] (1), mixed-valent tetranuclear [MnII2MnIII2(dcnm)2(hmp)6Cl2] (2) and the homo-valent hexanuclear [FeIII6(dcnm)6(hmp)8O2] (3), (where ipnm = imido[cyano (picolinoyl)methyl]nitrosomethanide, hmpH = 2-hydroxymethylpyridine; dcnm = dicyanonitrosomethanide) are reported. The formation of new dianionic ligand, ipnm which is also an imide derivative, represents the scarce example of metal-mediated in-situ dehydrogenative cross-coupling between amide derivatives with primary alcohol. Structure of 2 is known as ‘butterfly’ type structure while hexanuclear cluster 3 exists in chair-like conformation which in both structures, the dcnm acting as a terminal ligand.

A Facile and Microwave Assisted Solvent Free Synthesis of Novel Indole Pyrimidine Imide Derivatives

A series of novel indole derivatives bearing pyrimidine and cyclic imide scaffolds such as phthalic and maleic anhydrides has been designed and synthesized using both conventional and microwave irradiation (MW) methods under solvent free conditions. The title compounds have been developed by the reaction of 2-aminoo-4-hydroxy-6-(5,1-substituted-indol-3-yl) pyrimidine-5-carbonitrile with phthalic and maleic anhydrides individually using MW method. In addition, these target compounds were also synthesised under conventional heating method. A considerable increase in the reaction rate has been observed with better yields (90–92%) within 2–6 min using microwave irradiation in comparison to conventional thermal treatment.

Highly Polarized Benzo[k]fluoranthene Imide Derivatives: Large Solvatofluorochromism, Dual Fluorescence and Aggregation Induced Emission Associated with Excited-State Intramolecular Charge Transfer.

The highly conjugated imides, 9-diphenyl-aminobenzo[k]fluoranthene imide and N-phenylcarbazo[2,3-k]fluoranthene imide, were produced by Buchwald-Hartwig reaction of N-octyl-9,10-dibromobenzo[k]fluoranthene imide with diphenylamine. In a similar manner, reaction of the N-ethylhexyl-9,10-dibromo derivative with carbazole leads to formation of 9-(N-carbazoyl)benzo[k]fluoranthene imide. All the benzo[k]fluoranthene imide (BFI) derivatives in solution show remarkable solvatofluorochromism. Diphenylamino and 9-(N-carbazoyl) derivatives, having twisted structures, exhibit fluorescence bands at short wavelengths in highly polar solvents, and they emit dual fluorescence in acetone. Moreover, the 9-(N-carbazoyl) derivative displays aggregation-induced emission in highly aqueous acetone solutions. The results of density functional theory calculations demonstrate that a considerable spatial separation exists between the HOMO and LUMO coefficients of the N-arylamine substituted BFIs. The results indicate that the ground-to-excited state transitions of these compounds have intramolecular charge transfer character.

Density functional theory analysis for the limitations of fluoranthene-fused imide based small molecule acceptor materials in photovoltaic performance

Recently, the bulk-heterojunction (BHJ) organic photovoltaic cells (OPVs) have attracted more attention owing to their potentials in low-weight, cost-effective, semi-transparent, colorful, and flexible. As one of the most promising candidates non-fullerene small molecule acceptors (SMA) in BHJ OPVs, fluoranthene-fused imide (FFI) derivatives can effectively regulate energy level and absorption by functional modification of active sites on its backbone. Nevertheless, it is still a challenge to design molecules based on FFI materials to achieve significant improvements in optoelectronic performance. Therefore, the key to this work is to explore the influence of introducing functional substituents at different active sites of FFIs on the photoelectric properties. By introducing different number of substituent groups with different electron-withdrawing and electron-donating capacities at FFI backbones active sites, could lead to construct “D-A-D” structures. By density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations, we demonstrated that constructing “D-A-D” structure in FFI derivatives wouldn’t impact apparently on charge transfer process, because the nearly vertical dihedral angles exhibit in these geometrical configurations between between “D units” and “A units”. This has become a main factor limiting the performance improvement of FFI-based SMAs with “D-A-D” structures. On the contrary, it would be an effective approach to control the number of electron-withdrawing groups reasonably at FFI backbone in order to design more excellent performance for FFIs.

Preparation of platinum(II) complexes with naphthalene imide derivatives and exploration of their in vitro cytotoxic activities

Two new platinum(II) complexes with naphthalene imide derivatives as the ligands, [Pt(3a)Cl]Cl (3a-Pt) and [Pt(3b)Cl]Cl (3b-Pt), where 3a = 5‑(3‑(bis(pyridin‑2‑ylmethyl)amino)propoxy)‑2‑phenyl‑1H‑benzo[de]isoquinoline‑1,3(2H)‑dione and 3b = 2‑benzyl‑5‑(3‑(bis(pyridin‑2‑ylmethyl)amino)propoxy)‑1H‑benzo[de]isoquinoline‑1,3(2H)‑dione, were synthesized and structurally characterized. 3b-Pt showed higher anti-tumor properties in vitro against human non-small cell lung cancer NCI-H460 cells (0.89 ± 0.25 μM) than 3a-Pt (11.32 ± 0.47 μM) and cisplatin (11.09 ± 1.01 μM). In addition, 3b-Pt induced NCI-H460 cell apoptosis through inhibition of the telomerase activity and dysfunction of mitochondria.

Modification of polyhedral oligomeric silsesquioxane derivatives with heck reaction as possible new bio-hybrid materials

The regioselective synthesis of Polyhedral oligomeric silsesquioxane (POSS)-based norbornyl imide derivatives through palladium catalyzed Heck coupling reaction was reported on an effective synthetic method to organic–inorganic bio-hybrids serving as advanced materials. The reaction of POSS-based imide derivatives with various aryl iodides catalyzed by palladium acetate in the presence of triethyl amine, as the base, in DMF afforded the products in moderate yields. All new POSS derivatives were structurally characterized by FTIR, 1H, 13C NMR, HRMS and GC/MS analyses.

Synthesis of new polyhedral oligomeric silsesquioxane derivatives as some possible antimicrobial agents

1,3-Dipolar cycloaddition reactions were studied to synthesize Polyhedral oligomeric silsesquioxane (POSS)-based norbornyl imide derivatives containing izoxazoline groups in good yields. And also 1,3-dipolar cycloaddition reactions of azomethine ylides with POSS-based norbornene dipolarophiles for a synthesis of the novel POSS-based norbornane-fused spiro-1,3-indandionolylpyrrolidines are reported. All newly synthesized POSS compounds were structurally characterized by FTIR, 1H, 13C NMR, HRMS and GC/MS analyses.

Synthesis and iron coordination properties of schizokinen and its imide derivative.

The iron(iii) affinity constants for schizokinen and its imide derivative are reported for the first time. Surprisingly, schizokinen possesses a higher affinity for iron(iii) than desferrioxamine B; log KFeIII (FeL), 36.2 and 30.6, respectively. This increase in value is associated with the substitution of one hydroxamate function by an α-hydroxycarboxylate grouping. By virtue of the similarity of siderophore-iron(iii) complexes and siderophore-gallium(iii) complexes, schizokinen (which is a Gram positive siderophore) has potential for 68Ga PET-based imaging.

In vitro and in vivo activity of novel platinum(ii) complexes with naphthalene imide derivatives inhibiting human non-small cell lung cancer cells

3 induced NCI-H460 cell apoptosis via inhibition of the telomerase and dysfunction of mitochondria. Remarkably, 3 obviously inhibited NCI-H460 xenograft tumor growth in vivo.

Synthesis, Characterization and Antimicrobial Activities of Five and Six Member Cyclic Imides Derivatives

Synthesis, Characterization and Antimicrobial Activities of Five and Six Member Cyclic Imides Derivatives

(CH3)2CuLi/Cu(OTf)2 Mediated N- or O-Cyclization of Urea-Tethered Cyclobuta[ b]indolines.

A (CH3)2CuLi/Cu(OTf)2 mediated N- or O-cyclization of urea-tethered cyclobuta[ b]indolines has been reported in this paper, giving a new synthetic protocol for the construction of pyrimido[1,6- a]indolone and cyclic imidate derivatives in moderate to good yields with a broad substrate scope under mild conditions. A plausible reaction mechanism has been also proposed on the basis of previous reports and the control experiments.