Imide Derivatives Research Articles

Synthesis and Antimicrobial Activity of Mono, Di and Tri Substituted Aromatic Amines and Napthyl Amine Cyclic Imides Derivatives

Synthesis and Antimicrobial Activity of Mono, Di and Tri Substituted Aromatic Amines and Napthyl Amine Cyclic Imides Derivatives

Role of intrinsic hydrogen bonds in the assembly of perylene imide derivatives in solution and at the liquid-solid interface.

The impact of hydrogen bond formation on the supramolecular assembly of two perylene imide derivatives (PMAMI and PDINH) was systematically investigated in solution and at the liquid-solid interface. PDINH has intrinsic hydrogen bond sites, but this is not the case for PMAMI. The solution assembly was explored by morphological methods (SEM, AFM, TEM and cryo-TEM) and spectral characterization (UV-vis, FL, XRD, and FTIR spectra). The surface assembly at the liquid-solid interface was detected by scanning tunneling microscopy (STM). It was found that in a mixed solution (THF/MeOH, 10 v%/90 v%), PMAMI formed nanofibers together with large sheet structures and PDINH assembled into uniform nanosheets, suggesting different molecular packing routes. The assembled structures could be adjusted by varying the solvent polarity for both molecules. At the liquid-solid interface, clearly distinguished surface nanostructures from PMAMI and PDINH were easily observed. Based on all spectral and morphological characterizations, it was suggested that in solution the assembly of PMAMI was mainly derived by π-π stacking interactions; on the other hand, the synergetic interaction of hydrogen bonds and π-π stacking was the reason for the hierarchical assembly of PDINH. Hydrogen bonds could be formed both for PMAMI and PDINH and stabilized nanostructures at the liquid-solid interface. This investigation could be useful in designing perylene imide-based building blocks for fabricating supramolecular assemblies with predetermined nanostructures and properties.

Synthesis of Chiral Heterocyclic N‐Haloamides and ‐imides and Their Applications as Halogenating Agents and Mechanistic Probes

N‐Haloamides and ‐imides are standard halogenating agents and have been used in radical as well as electrophilic halogenation reactions. Despite their many applications, there are only few reports of chiral derivatives of the most common of these reagents such as N‐halosuccinimides. Herein, we report the synthesis of new chiral N‐halogenated amides and imide derivatives, which are easily accessible from inexpensive starting materials of the chiral pool. These new chiral halogenating agents were then applied as stoichiometric reagents in haloetherification reactions and as mechanistic probes in organocatalytic halocyclization reactions.

Solvent free, catalyst free, microwave or grinding assisted synthesis of bis-cyclic imide derivatives and their evaluation for anticancer activity

Cyclic imides are well known to be very important antitumor agents such as mitonafide and amonafide etc. Based on this fact, we have synthesized two series of cyclic imide derivatives containing two cyclic imide moiety in their structures (bis-cyclic imides) and screened them for in vitro anticancer activity against five human cancer cell lines i.e. breast (T47D), lung (NCl H-522), colon (HCT-15), ovary (PA-1) and liver (Hep G2). One series of bis-cyclic imide derivatives (3a–h) have been synthesized by condensation of acid anhydrides (1a–b) with diamines (2a–d) and another series (9a–f, 10a–f, 11a–f and 12a–f) by condensation of various diamines (4a–f) with diacids (5–8) in good yields. Structures assigned to 3a–h, 9a–f, 10a–f, 11a–f and 12a–f were fully characterized by spectroscopic means and elemental analysis. On screening for in vitro anticancer activity, compounds 3a (breast T47D), 3d (breast T47D, liver Hep G2), 3e (breast T47D, liver Hep G2), 3h (colon HCT-15), 10f (liver Hep G2) and 11a (colon HCT-15, ovary PA-1) exhibited good anticancer activities with IC50 values range from 12.41±3.2 to 17.9±2.5μM.

Why chiral tartaric imide derivatives give large helical twisting powers in nematic liquid crystal phases: substituent-effect approach to investigate intermolecular interactions between dopant and liquid crystalline molecules

ABSTRACTNovel C2-symmetric chiral dopant derivatives, namely, N-substituted (2R, 3R)-2,3-bis(4-(4-octyloxyphenyl)benzoyloxy)succinimides1a-h, were synthesised, and the effects of the N-substituent and imide-carbonyl groups on the helical twisting powers (HTPs) were investigated in two nematic liquid crystalline compounds, 4-n-pentyl-4ʹ-cyanobiphenyl (5CB) and N-(4-ethoxybenzylidene)-4-n-butylaniline (EBBA). As a result, it was clarified that the bulkiness of the N-substituents has a significant correlation with the HTPs, and the imide-carbonyl group interacts strongly with the cyano group of 5CB to give high HTPs in the nematic phases. However, it is assumed that the imide-carbonyl groups of the dopants do not have strong electrostatic attractive interactions with EBBA molecules in the nematic phase to afford the moderate HTPs.

Synthesis, Structures, and Photophysical Properties of Difuro‐Fused Tetrahydro[5]helicene Imide Derivatives

AbstractBy using Sonogashira coupling reactions and iodine cyclization reactions, diiodide difuro‐fused tetrahydro[5]helicene imides were conveniently synthesized, which then gave a series of functionalized difuro‐fused tetrahydro[5]helicene imide derivatives by Suzuki–Miyaura cross‐coupling reactions. The crystal structures showed that the aromatic imide dyes had π‐extended and helical structures, and could pack into herringbone‐like architectures. Moreover, the imide dyes also showed intense fluorescence and redshifted emissions in both solution and spin‐coated films because of the expanded π‐conjugation systems and the helical twisted structures.

Synthesis of Perylene Imide Diones as Platforms for the Development of Pyrazine Based Organic Semiconductors.

There is a great interest in peryleneimide (PI)-containing compounds given their unique combination of good electron accepting ability, high abosorption in the visible region, and outstanding chemical, thermal, and photochemical stabilities. Thus, herein we report the synthesis of perylene imide derivatives endowed with a 1,2-diketone functionality (PIDs) as efficient intermediates to easily access peryleneimide (PI)-containing organic semiconductors with enhanced absorption cross-section for the design of tunable semiconductor organic materials. Three processable organic molecular semiconductors containing thiophene and terthiophene moieties, PITa, PITb, and PITT, have been prepared from the novel PIDs. The tendency of these semiconductors for molecular aggregation have been investigated by NMR spectroscopy and supported by quantum chemical calculations. 2D NMR experiments and theoretical calculations point to an antiparallel π-stacking interaction as the most stable conformation in the aggregates. Investigation of the optical and electrochemical properties of the materials is also reported and analyzed in combination with DFT calculations. Although the derivatives presented here show modest electron mobilities of ∼10-4 cm2V-1s-1, these preliminary studies of their performance in organic field effect transistors (OFETs) indicate the potential of these new building blocks as n-type semiconductors.

Amidoalkylation of aromatic hydrocarbons by meathylol and ethylol derivatives of imides

Amidoalkylation of aromatic hydrocarbons by meathylol and ethylol derivatives of imides

Distinct molecular structures and hydrogen bond patterns of α,α-diethyl-substituted cyclic imide, lactam, and acetamide derivatives in the crystalline phase

α,α-Dialkyl- and α-alkyl-α-aryl-substituted cyclic imides, lactams, and acetamides show promising anticonvulsant, anxiolytic, and anesthetic activities. While a number of crystal structures of various α-substituted cyclic imides, lactams, and acetamides were reported, no in-depth comparison of crystal structures and solid-state properties of structurally matched compounds have been carried out so far. In this paper, we report molecular structure and intermolecular interactions of three α,α-diethyl-substituted compounds – 3,3-diethylpyrrolidine-2,5-dione, 3,3-diethylpyrrolidin-2-one, and 2,2-diethylacetamide – in the crystalline phase, as studied using single-crystal X-ray diffraction and IR spectroscopy. We found considerable differences in the patterns of H-bonding and packing of the molecules in crystals. These differences correlate with the compounds’ melting points and are of significance to physical pharmacy and formulation development of neuroactive drugs.

Ultrafast Investigation of Intramolecular Charge Transfer and Solvation Dynamics of Tetrahydro[5]-helicene-Based Imide Derivatives.

We report the excited-state intramolecular charge transfer (ICT) characteristics of four tetrahydro[5] helicene-based imide (THHBI) derivatives with various electron-donating substitutes in different polarity of solvents using steady-state, time-resolved transient absorption (TA) spectroscopy. It is found that, the small bathochromic-shift of the absorption spectra but large red shift of the emission spectra for all dyes with increasing solvent polarity indicates the larger dipole moment of the excited state compared to ground state. The results of theoretical calculations exhibit the charge transfer from the terminal donors to helical backbone, which accounts for the degrees of red shift of the emission spectra from different extent of ICT nature. Time-resolved TA spectra recorded as a function of electron-donating substitutes and solvent polarity show the dye with stronger donors (THHBI-PhNPh2) in more polar solvent behaves faster excited-state ICT relaxation, leading to the formation of solvent-stabilized ICT state (ICT’ state) from the excited ICT state; The dyes (THHBI-Ph, THHBI-PhCF3 and THHBI-PhOMe) with relative weaker donors show weaker dependence on solvent polarity, and instead of that intersystem crossing (ISC) becomes possible from ICT state to triplet state.

Синтез та алкілування аміду, отриманого на основі N-фталоілгліцину та гідразиду ендикової кислоти

Himic acid hydrazide derivatives are promising in terms of practical use compounds due to their wide range of biological effects (primarily neurotropic activity) and their synthetic potential. Earlier investigated in detail the methods of synthesis of hydrazones, urea, amide and imide derivatives of himic acid hydrazide. Also known diverse biological action of N-Phthaloylglycine, which could serve as an effective protection for the amino group of glycine and has interesting structural features that contribute to the formation of supramolecular complexes. The methodology of synthesis of 2-(Phthalimidoyl)-N-benzyl-N-(4-azatricyclo[5.2.1.02-endo,6-endo]dec-8-ene-3,5-dione-4-yl)acetamide, including obtaining of 2-(Phthalimidoyl)-N-(4-azatricyclo[5.2.1.02-endo,6-endo]dec-8-ene-3,5-dione-4-yl)acetamide based on himic acid hydrazide acid and Phthalylglycyl chloride and alkylation of obtained product. Found that acceptable yield is observed during the alkylation reaction in boiling solution of anhydrous acetone in the presence of excess calcined potassium carbonate. The structure of obtained products was confirmed by analyzing the 1H NMR spectrum.

Phthalimide Compounds Containing a Trifluoromethylphenyl Group and Electron-Donating Aryl Groups: Color-Tuning and Enhancement of Triboluminescence.

Trifluoromethylphenyl-substituted phthalimide derivatives favorably form triboluminescence (TL) active noncentrosymmetric crystals. Oligothienyl-, oligophenyl-, and naphthyl-substituted phthalimide derivatives were successfully developed as a series of metal free TL compounds. X-ray crystal structure analyses of bithienyl and naphthyl derivatives revealed noncentrosymmetric layer structures in the same direction. Introduction of suitable electron rich π-units such as thienyl groups enhances their photoluminescence and TL characteristics, and the colors can be also controlled in the visible region. A rigid naphthyl-substituted imide derivative exhibits extremely high TL performance.

Studies towards development of asymmetric double-Mannich reactions of chiral 2-oxocyclohexanecarboxylate derivatives with bis(aminol)ethers

A range of chiral ester and chiral imide derivatives of 2-oxocyclohexanecarboxylic acid were utilised in double-Mannich reactions with bis(aminol)ethers to develop an asymmetric synthesis of azabicyclo[3.3.1]nonanes. An improved method for the double-Mannich reaction of β-ketoesters and bis(aminol)ethers using sub-stoichiometric quantities of a Lewis acid was developed. Additionally, a sequential, double-Mannich approach was investigated incorporating chiral auxiliaries into N,O-acetals. The use of oxazolidinone auxiliaries afforded the best yields and diastereoselectivities enabling separation of the resulting diastereomers of the azabicyclo[3.3.1]nonanes.

Synthesis and preliminary studies of biological activity of amino derivatives of 4-azatricyclo- [5.2.1.02,6]dec-8-ene-3,5-dione with silicon in the structure

Abstract A series of 38 new derivatives of cyclic imides containing silicon in the structure was synthesized and characterized by 1H NMR, ESI-MS, and elemental analysis. Selected compounds (1l,m, 1g, 1o,p, 2l,m, and 2o,p) were tested for their cytotoxic properties in human chronic myelogenous leukemia (K562), human cervical cancer (HeLa), and normal endothelial cells (HUVEC). Seven compounds showed significant cytotoxicity. In addition, two compounds (1l and 2l) were tested toward affinity for 5-HT1A, 5-HT6, and 5-HT7 serotonin receptors, and all aryl/heteroarylopiperazino derivatives were tested for antimicrobial activity. The compounds tested toward affinity for selected serotonin receptors showed high and moderate affinity for 5-HT1A and 5-HT7, while the antimicrobial activity of tested compounds was not significant.

Organic fluorine involved intramolecular hydrogen bonds in the derivatives of imides: NMR evidence corroborated by DFT based theoretical calculations

The rare occurrence of intramolecular hydrogen bonds (HBs) of the type N–H⋯F–C is detected in the derivatives of imides in a low polarity solvent by using multi-dimensional and multinuclear NMR experiments.

“Synthesis and Characterization of same Imide Schiff’s bases Derived for Trimethoprim and their biological evaluation”

Synthesis and characterization mono imides derivatives for trimethoprim, through reaction of the later with one mole of maleic and phthalic anhydrides, using the classical reflux methods in addition to the microwave technique in the presence of glacial acetic acid. Conversion of mono imides derivatives prepared in (1) above to the Schiff`s bases by the condensation with substituted aromatic aldehydes or ketones, using conventional method and microwave technique. So that imides-imines derivatives have been prepared. All the compounds prepared above have been characterized by using the physical constant by recording the malting points and using the spectroscopic methods such as UV-Visible, FT-IR and H1NMR spectroscopy. Study the biological activity of some selected new compounds as anti-bacterial against four types of bacteria (Pseudomona aruginons , Escherichia coli , Staphylococcus aureus and Enterococcus faecalis) isolates by Biomerixe co. using the disk diffusion method. This study showed high biological activity of most prepared compound against the studying bacteria.

Synthesis of Oxadiazolo-, Pyrimido-, Imidazolo-, and Benzimidazolo-Containing Derivatives of 1,4-Benzodiazepin-5-(4′-methylpiperazinyl)-carboxamide Through Phenylamino Spacer

Versatility of amidine and imidate derivatives of 5-carboxamido-1,4-benzodiazepin-5-(4′-methylpiperazinyl)-carboxamide (8 and 9) was explored to provide easy access to its 2-(oxadiazolo, pyrimido, imidazolo, and benzimidazolo)-substituted analogs 10, 11, 13, and 14, respectively, through the phenylamino spacer.

Rh(III)-catalyzed oxidative amidation of aldehydes: An efficient route to N-pyridinamides and imides

A novel Rh(III)-catalyzed direct amidation of aldehydes featuring Ag2CO3 as the oxidant is described. This selective procedure provides a variety of N-pyridinamides and imide derivatives in good yields.

Synthesis of Biopolymers by Condensed Histidine Imide Derivatives with Some Acid Anhydride and Their Crosslink with Acrylonitrite

Histidine as known amino acid was converted to its acid chloride [C1] with thionyl chloride at 0 oC, then reacted with ammonia, the corresponding imide-diamine [C2] was obtained, and then condensed with maleic or methylnadic anhydride. The two novel condensed polymers [C3, C4] were obtained with highly conversion percentage and modified to crosslinked polymers [C5, C6] with acrylonitrile monomer through vinylic group by free radical polymerization.
 The physical properties of all prepared polymers were studied and characterized by 1H-NMR, FT-IR and UV-visible spectroscopy. The swelling % was calculated.
 The new Polymers [C3, C4], were synthesized by direct polycondensation to give the new bioactive polymers. The rate of hydrolysis of the prepared polymers was studied in different pH values at 37 oC. Howeve, the crosslinked biopolymers [C5, C6] indicated much more chemical resistance than [C3, C4], and the sustained release was observed as good results in basic medium.

Synthesis and Reactions of New Chiral Linear Carboxamides with an Incorporated Peptide Linkage Using Nalidixic Acid and Amino Acids as Starting Materials

4b A series of chiral linear carboxamide derivatives (2- 15) with an incorporated peptide linkage have been prepared via the coupling of 1-ethyl-1,4-dihydro-7-methyl-4-oxo-quinoline-3-carboxylic acid (nalidixic acid, 1) with appropriate amino acid methyl esters. Coupling of 1 with amino acid methyl esters gave the corresponding peptide methyl esters 2, which were hydrolyzed with methanolic sodium hydroxide to the corresponding acids 3. Hydrazinolysis of esters 2with hydrazine hydrate afforded the corresponding acid hydrazide derivatives 4. The latter compounds were coupled with appropriate aldehydes or acetophenone derivatives to afford the corresponding Schiff base derivatives 5 and 6, respectively. The hydrazide derivative was reacted with phenyl isothiocyanate or carbonyl derivatives to give the corresponding thiosemicarbazide 7 and compounds 8- 10, respectively. Also, 4b was treated with acid monoanhydrides to give the corresponding imide derivatives 11- 13. Finally, 4b was reacted with tetracarboxylic acid dianhydride derivatives to afford the corresponding diimido carboxamide derivatives 14 and 15