Naphthyl Derivatives Research Articles

Liquid crystalline naphthyl derivatives with bromoalkoxy tail: Photophysical behavior and DFT studies

One new homologous series of mesogenic bromoalkoxy terminated naphthyl derivatives containing flexible spacers as well as azo and ether linkages was synthesized by the etherification of an azo dye (E)-4-(naphthalen-2-yldiazenyl) phenol with various α, ω-dibromo-alkanes, respectively. Compounds in the present work were convinced with respective right structures confirmed with various spectroscopic techniques. Thermotropic properties of the compounds were investigated. Among all the compounds, compounds with flexible spacer (n = 4, 5, 6) exhibited excellent liquid crystalline nature. Structure–property relationships, the influence of different flexible spacers, the mesophase ranges and the photo-isomerization of liquid crystalline compounds were studied. The photophysical behavior was gained by UV–visible spectroscopy and optical properties were determined with a spectroscopic ellipsometer. Computational studies of all molecular structures were performed with satisfactory explanation to attribute mesogenic and optical properties. It's worth noting that synthesized mesogenic materials are excellent dielectrics making them suitable for electronic and industrial applications, as well as having a suitable refractive index making them suitable for light-guiding phenomena.

Green synthesis of naphthyl derivative as an optical sensor for the detection of l-carnitine in food samples.

An economical and green approach to the synthesis of naphthyl derivative for detection of l-carnitine (3-hydroxy-4-N-trimethyl-aminobutyrate) is practically important. We developed a naphthyl derivative as a probe showing 'turn-on' response towards l-carnitine selectively at pH 7.2 through ICT mechanism with a good limit of detection (LOD) of 0.126 μM. Using Job's plot for determining the binding stoichiometry, it was found that probe could form a more stable complex (1:1) with carnitine. The binding constant (K) between probe and carnitine was calculated as 8 × 107 M-1 using the Benesi-Hildebrand plot. The binding interaction of the probe with l-carnitine was confirmed by nuclear magnetic resonance titrations, Fourier-transform infrared spectroscopy, photo physical studies and density functional theory calculations. Meanwhile, the probe can be used to quantitatively detect carnitine in food samples.

SYNTHESIS AND MOLECULAR DOCKING STUDIES ON BIOLOGICALLY ACTIVE PYRAZOLE TERMINATED IMINO NAPHTHYL DERIVATIVES

In this present study, a series of pyrazole terminated imino naphthyl derivatives were synthesized by the condensation reaction between 1,3 - diphenyl pyrazol-4-carboxaldehyde with substituted aromatic amines. The compounds were analyzed for their in vitro antimicrobial activities against some bacterial and fungal species and compared with the standard drugs. The molecular docking studies with protein and DNA were also carried out and revealed that all the synthesized compounds showed moderate to good biological activities, both experimentally and theoretically.

Synthesis and anti-Toxoplasma activity of indole-triazole compounds on tachyzoites of RH strain

BackgroundConventional treatment for toxoplasmosis have severe side effects and the inability to completely eradicate the disease. Therefore, the acquisition of new anti-Toxoplasma drugs has always been of interest among researchers. In the present study, we prepare a new indole-triazole derivatives and evaluated their potential anti-parasitic activity against tachyzoites of Toxoplasma RH strain. Materials and methodsIn this study, after synthesis of the two new compounds of indole-triazole, the effect of their different concentrations (2–1024 μg/ml) were determined on Toxoplasma tachyzoites using flow cytometry. Furthermore, tachyzoites were exposed to different concentrations of compounds (4, 16, 64, 265, 1024 μg/ml) for 1.5 h and their infectivity were evaluated in BALB/c mice. ResultsThe flow cytometry results indicated the benzyl derivative of indole-triazole in various concentrations had a lethal effect on tachyzoites between 11.93% and 89.66%, while the naphthalene derivative had a lethality of 26.63%–66.82%. The infectivity analysis showed that the survival time of mice at concentrations of 1024 μg/ml and 512 μg/ml of benzyl derivatives was significantly increased (P = 0.008 and P = 0.016, respectively), compared to that in the negative control group. Furthermore, survival time of mice was statistically significant at the concentration of 1024 μg/ml for naphthyl derivative (P = 0.012). ConclusionFindings of the current study suggested indole triazole compounds, based on their structure and enzymes targeting, have a considerable effect on tachyzoites of T. gondii RH strain and can be considered as a new anti-Toxoplasma agent.

Synthesis, DNA Binding, DFT Calculations and Molecular Docking Studies of Biologically Active N-((3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)naphthyl Derivatives

Six novel pyrazole compounds were synthesized, characterized and its antimicrobial activity was also evaluated. In vitro antibacterial activity against diverse bacterial and fungal strains was tested and the results were compared to the standard drug. The DNA binding properties of calf thymus DNA (ct-DNA) were investigated using electronic absorption and fluorescence spectroscopies . The software performed computer-aided molecular docking experimentations on proteins and (ct-DNA). Synthesized compounds revealed moderate to satisfactory biological activities both experimentally and theoretically.

Synthesis, DFT Calculations, DNA Binding and Molecular Docking Studies on Biologically Active N-((3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl)methylene)naphthyl Derivatives

The biologically active pyrazole clubbed imino naphthyl derivatives have been designed and synthesized from 1-phenyl-3-methoxy phenyl-1H-pyrazol-4-carboxaldehyde and substituted naphthyl amines via acid catalyzed condensation reaction. All the synthesized compounds were well characterized by different spectroscopic and mass spectral techniques. The in vitro antibacterial, antifungal and antituberculosis studies were carried out. The molecular docking study was also done with the software Arguslab 4.0.1. The studied compounds showed moderate to good biological activities both experimentally and theoretically. Geometry optimization, DNA binding interaction and FMO analysis were also investigated with the help of Gaussian 16 package at B3LYP/6-31G(d,p) level.

Deep-blue organic light-emitting diodes based on multi-tert-butyl modified naphthylene

Six tert-butyls modified naphthyl derivative (2,6-di-tert-butyl-1,5-bis-(3,5-di-tert-butyl-phenyl)-naphthalene (N(dtb)4) was synthesized and tested for host and guest materials in organic light-emitting diodes (OLEDs). Blue OLED using N(dtb)4 as a host and an emitter DSA-PH as a guest reaches an efficiency of 11.52 cd·A−1 (maximum external quantum efficiency 7.8 % and maximum power efficiency 10.33 lm·W−1). In addition, for the OLED with N(dtb)4 being a guest, we find that the concentrations of N(dtb)4 will also affect the performance of the OLED, among which ADN: 5 wt.% N(dtb)4 has higher efficiency, and the maximum current efficiency, external quantum efficiency (EQE) and power efficiency of the device reach 3.75 cd·A−1, 3.93 % and 3.36 lm·W−1, respectively. We also investigated the pure N(dtb)4 -based ultraviolet OLED (UV-OLED), and achieved the maximum EQE of the device is 1.12 %. These results indicate that N(dtb)4, a novel synthesized fluorescent organic material, has great potential applications in OLEDs and accordingly advancing lightings and displays.

Exploring naphthyl derivatives as SARS-CoV papain-like protease (PLpro) inhibitors and its implications in COVID-19 drug discovery.

Novel coronavirus disease 2019 (COVID-19) emerges as a serious threat to public health globally. The rapid spreading of COVID-19, caused by severe acute respiratory syndrome (SARS) coronavirus 2 (SARS-CoV-2), proclaimed the multitude of applied research needed not only to save the human health but also for the environmental safety. As per the recent World Health Organization reports, the novel corona virus may never be wiped out completely from the world. In this connection, the inhibitors already designed against different targets of previous human coronavirus (HCoV) infections will be a great starting point for further optimization. Pinpointing biochemical events censorious to the HCoV lifecycle has provided two proteases: a papain-like protease (PLpro) and a 3C-like protease (3CLpro) enzyme essential for viral replication. In this study, naphthyl derivatives inhibiting PLpro enzyme were subjected to robust molecular modelling approaches to understand different structural fingerprints important for the inhibition. Here, we cover two main aspects such as (a) exploration of naphthyl derivatives by classification QSAR analyses to find important fingerprints that module the SARS-CoV PLpro inhibition and (b) implications of naphthyl derivatives against SARS-CoV-2 PLpro enzyme through detailed ligand–receptor interaction analysis. The modelling insights will help in the speedy design of potent broad spectrum PLpro inhibitors against infectious SARS-CoV and SARS-CoV-2 in the future.Graphical Supplementary InformationThe online version contains supplementary material available at(10.1007/s11030-021-10198-3) .

Synthesis of the highly porous semiconductors with different electrical features using isostructural metal-organic frameworks as precursor

Two C/ZnO nanocomposites and one C/Zn nanocomposite were synthesized by thermal decomposition of the prepared isostructural metal–organic frameworks with slight differences in their nature. The precursors of the C/ZnO and the C/Zn nanocomposites contain phenyl derivatives in oxidized or reduced state and naphthyl derivative, respectively. The titled nanocomposites consist of the high porosity, 902, 1117 and 583 m2/g, respectively. The as-prepared nanocomposites have been characterized by X-ray powder diffraction (PXRD) analysis and elemental mapping. The size and morphology of the samples were studied using field emission scanning electron microscopy (FE-SEM). The results indicated that the synthesized porous nanocomposites as the semiconductor materials displayed good electrical conductivity with different specific resistances.

New naphthyl derivatives from Aspergillus californicus.

Two new naphthyl-products calinaphthyltriol A (1) and calinaphthalenone A (2) were isolated from Aspergillus californicus IBT 16748 together with one known compound ophiobolin X (3). Their structures were elucidated by extensive spectroscopic analyses. The absolute configuration of 2 was solved by comparing its optical rotation with data for the known compounds 4, 5, and 6 as well as theoretical calculations. The antibacterial and cytotoxic activities of 1 and 3 were evaluated. Both compounds did not show antibacterial activity (MIC > 96 µg·ml-1) against a few selected clinically relevant Gram positive and Gram negative bacterial strains. However, they showed moderate cytotoxicity against HL-60 cell line with IC50 values of 18 and 24 µg·ml-1, respectively.

Gem-Dichlorocyclopropanation of Dicarbonyl Derivatives.

A novel methodology for the 1,1-dichlorocyclopropanation of dicarbonyl conjugated olefins was described. The developed protocol is simple and uses readily accessible starting materials, allowing the isolation of the desired adducts in moderate to excellent yields (up to 99 %). Furthermore, the reaction tolerated scale up to the gram scale; thus highlighting the synthetic potential of this transformation. Control experiments and DFT studies revealed that the reaction proceeded through a Michael-initiated ring-closure process, in which reaction temperature played a crucial role. Finally, these gem-dichlorocyclopropanes were also employed in the preparation of a trisubstituted naphthyl derivative and a diastereoselective reduction was also demonstrated.

Effective Inhibitors of Tyrosyl-DNA Phosphodiesterase 1 Based on Monoterpenoids as Potential Agents for Antitumor Therapy

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is one of the important DNA repair enzymes responsible for the repair of DNA damage caused by anticancer drugs, such as topotecan. In this regard, enzyme activity is one of the possible causes of tumor resistance to chemotherapy, and the use of inhibitors of this enzyme is considered as a promising adjuvant therapy. We have obtained a number of new isomeric naphthyl derivatives of thiophenyl octahydro-2H-chromene, the structure of one of which is confirmed by X-ray structural analysis. Based on molecular modeling data, the structure of the ligand-Tdp1 complex has been proposed. All compounds obtained inhibit Tdp1 at a concentration of about 2 μM. Low toxicity of three compounds was shown, which makes them promising candidates for the development of accompanying cancer therapy.

A 3-(4-nitronaphthen-1-yl) amino-benzoate analog as a bifunctional AKR1C3 inhibitor and AR antagonist: Head to head comparison with other advanced AKR1C3 targeted therapeutics

Drugs used for the treatment of castration resistant prostate cancer (CRPC) include Abiraterone acetate (Zytiga®) and Enzalutamide (XTANDI®). However, these drugs provide clinical benefit in metastatic disease for only a brief period before drug resistance emerges. One mechanism of drug resistance involves the overexpression of type 5 17-β-hydroxysteroid dehydrogenase (aldo-keto reductase 1C3 or AKR1C3), a major enzyme responsible for the formation of intratumoral androgens that activate the androgen receptor (AR). 3-((4-Nitronaphthalen-1-yl)amino)benzoic acid 1 is a “first-in-class” AKR1C3 competitive inhibitor and AR antagonist. Compound 1 was compared in a battery of in vitro studies with structurally related N-naphthyl-aminobenzoates, and AKR1C3 targeted therapeutics e.g. GTx-560 and ASP9521, as well as with R-bicalutamide, enzalutamide and abiraterone acetate. Compound 1 was the only naphthyl derivative that was a selective AKR1C3 inhibitor and AR antagonist in direct competitive binding assays and in AR driven reporter gene assays. GTx-560 displayed weak activity as a direct AR antagonist but had high potency in the AR reporter gene assay consistent with its ability to inhibit the co-activator function of AKR1C3. By contrast ASP9521 did not act as either an AR antagonist or block AR reporter gene activity. Compound 1 was the only compound that showed comparable potency to inhibit AKR1C3 and act as a direct AR antagonist. Compound 1 blocked the formation of testosterone in LNCaP-AKR1C3 cells, and the expression of PSA driven by the AKR1C3 substrate (4-androstene-3,17-dione) and by an AR agonist, 5α-dihydrotestosterone consistent with its bifunctional role. Compound 1 blocked the nuclear translocation of the AR at similar concentrations to enzalutamide and caused disappearance of the AR from cell lysates. R-biaclutamide and enzalutamide inhibited AKR1C3 at concentrations 200x greater than compound 1, suggesting that its bifunctionality can be explained by a shared pharmacophore that can be optimized.

Synthesis and properties of π-extended fluoranthene derivatives from 1,2-diarylacenaphthylene derivatives

Acenaphthylene units work as a useful platform for the synthesis of polycyclic aromatic hydrocarbons (PAH). Three 1,2-diarylacenaphthylene derivatives (9-phenanthryl, 7-t-butyl-2-pyrenyl and 2-naphthyl) were prepared by Suzuki-Miyaura coupling of 1,2-dibromoacenaphthylene with the corresponding boronic acids and ester. The Scholl reaction of the phenanthryl derivative affords a donor-acceptor type fluoranthene derivative possessing a hemi-coronene structure by forming two CC bonds between phenanthryl groups. The reaction of the pyrenyl derivative allows one CC bond formation to give a helicene-type fluoranthene derivative. The reaction of the naphthyl derivative provides an asymmetric fluroranthene derivative having an anthracene unit accompanied with one CC bonding reaction, while a photochemical cyclization followed by dehydroaromatization reaction of the compound gives a symmetric fluoranthene derivative with a [5]helicene structure.

Mesogenic Terminal Naphthyl Derivatives with Azomethine/Azo and Ester Central Linkages

Mesogenic Terminal Naphthyl Derivatives with Azomethine/Azo and Ester Central Linkages

EuIII‐Based Nanolayers as Highly Efficient Downshifters for CIGS Solar Cells

We report herein on the use of 13 ternary europium(III) complexes as downshifting (DS) material for copper indium gallium selenide (CIGS) solar cells. Their general formulae are [Eu(β‐Dik)3(NL)x] and [Eu(L)3], in which β‐Dik = 2‐thenoyltrifluoroacetonate, 4,4,4‐trifluoro‐1‐phenyl‐1,3‐butanedione and 4,4,4‐trifluoro‐1‐(2‐naphthyl)‐1,3‐butanedione and NL = diphenyl sulfoxide (x = 2), triphenylphosphine oxide (x = 2), bis[2‐(diphenylphosphino)phenyl] ether (x = 1), 5,6‐epoxy‐5,6‐dihydro‐1,10‐phenanthroline (x = 1) and 2‐(N,N‐diethylanilin‐4‐yl)‐4,6‐bis(3,5‐dimethylpyrazol‐1‐yl)‐1,3,5‐triazine (x = 1) and L = 4‐(4′‐tert‐butylbiphenyl‐4‐yl)‐2,2′‐bipyridine‐6‐carboxylate. Tris(β‐diketonate) ternary EuIII complexes are very good candidates for DS applications, and some of them have shown very promising results when embedded in a host organic polymer matrix typically used for solar cell encapsulations. Herein we report a new method for the direct deposition of luminescent nanolayer films on CIGS solar cells. Highly luminescent nano‐ and microlayer films with a thickness in the range of 150 nm to 10 µm have been obtained and characterized by optical microscopy, profilometry, spectrofluorimetry and external quantum efficiency (EQE) measurements. The efficient conversion of incident photons into red light was observed for films with a thickness of 400–600 nm, leading to a significant improvement in the EQE and short‐circuit current density (Jsc) in the UV region up to 0.81 mA/cm2. The absolute conversion efficiency increased by up to 0.8 %. The nanofilms, with the exception of those containing naphthyl derivatives, were found to be photostable and therefore represent a competitive alternative to doped polymer encapsulants.

Novel selective, potent naphthyl TRPM8 antagonists identified through a combined ligand- and structure-based virtual screening approach

Transient receptor potential melastatin 8 (TRPM8), a nonselective cation channel, is the predominant mammalian cold temperature thermosensor and it is activated by cold temperatures and cooling compounds, such as menthol and icilin. Because of its role in cold allodynia, cold hyperalgesia and painful syndromes TRPM8 antagonists are currently being pursued as potential therapeutic agents for the treatment of pain hypersensitivity. Recently TRPM8 has been found in subsets of bladder sensory nerve fibres, providing an opportunity to understand and treat chronic hypersensitivity. However, most of the known TRPM8 inhibitors lack selectivity, and only three selective compounds have reached clinical trials to date. Here, we applied two virtual screening strategies to find new, clinics suitable, TRPM8 inhibitors. This strategy enabled us to identify naphthyl derivatives as a novel class of potent and selective TRPM8 inhibitors. Further characterization of the pharmacologic properties of the most potent compound identified, compound 1, confirmed that it is a selective, competitive antagonist inhibitor of TRPM8. Compound 1 also proved itself active in a overreactive bladder model in vivo. Thus, the novel naphthyl derivative compound identified here could be optimized for clinical treatment of pain hypersensitivity in bladder disorders but also in different other pathologies.

Spectroscopic studies of the intramolecular hydrogen bonding in o-hydroxy Schiff bases, derived from diaminomaleonitrile, and their deprotonation reaction products

The structural study of five Schiff bases derived from diaminomaleonitrile (DAMN) and 2-hydroxy carbonyl compounds was performed using 1H, 13C and 15N NMR methods in solution and in the solid state as well. ATR-FTIR and X-Ray spectroscopies were used for confirmation of the results obtained by NMR method. The imine obtained from DAMN and benzaldehyde was synthesized as a model compound which lacks intramolecular hydrogen bond. Deprotonation of all synthesized compounds was done by treating with tetramethylguanidine (TMG). NMR data revealed that salicylidene Schiff bases in DMSO solution exist as OH forms without intramolecular hydrogen bonds and independent on the substituents in aromatic ring. In the case of 2-hydroxy naphthyl derivative, the OH proton is engaged into weak intramolecular hydrogen bond. Two of imines (salDAMN and 5-BrsalDAMN) exist in DMSO solution as equilibrium mixtures of two isomers (A and B). The structures of equilibrium mixture in the solid state have been studied by NMR, ATR-FTIR and X-Ray methods.The deprotonation of three studied compounds (salDAMN, 5-BrsalDAMN, and 5-CH3salDAMN) proceeded in two different ways: deprotonation of oxygen atom (X form) or of nitrogen atom of free primary amine group of DAMN moiety (Y form). For 5-NO2salDAMN and naphDAMN only one form (X) was observed.

Crystal Structure and Functional Characterization of an Esterase (EaEST) from Exiguobacterium antarcticum.

A novel microbial esterase, EaEST, from a psychrophilic bacterium Exiguobacterium antarcticum B7, was identified and characterized. To our knowledge, this is the first report describing structural analysis and biochemical characterization of an esterase isolated from the genus Exiguobacterium. Crystal structure of EaEST, determined at a resolution of 1.9 Å, showed that the enzyme has a canonical α/β hydrolase fold with an α-helical cap domain and a catalytic triad consisting of Ser96, Asp220, and His248. Interestingly, the active site of the structure of EaEST is occupied by a peracetate molecule, which is the product of perhydrolysis of acetate. This result suggests that EaEST may have perhydrolase activity. The activity assay showed that EaEST has significant perhydrolase and esterase activity with respect to short-chain p-nitrophenyl esters (≤C8), naphthyl derivatives, phenyl acetate, and glyceryl tributyrate. However, the S96A single mutant had low esterase and perhydrolase activity. Moreover, the L27A mutant showed low levels of protein expression and solubility as well as preference for different substrates. On conducting an enantioselectivity analysis using R- and S-methyl-3-hydroxy-2-methylpropionate, a preference for R-enantiomers was observed. Surprisingly, immobilized EaEST was found to not only retain 200% of its initial activity after incubation for 1 h at 80°C, but also retained more than 60% of its initial activity after 20 cycles of reutilization. This research will serve as basis for future engineering of this esterase for biotechnological and industrial applications.

Mesogenic naphthyl derivatives

ABSTRACTTwo new mesogenic homologous series of liquid crystalline naphthalene derivatives with different central linkages: 2- Naphthyl-4-n-alkoxybenzoates (I) and trans-2-Naphthyl -4-n –alkoxycinnamates(II), have been synthesized and characterized by a combination of elemental analysis and standard spectroscopic methods. Twelve compounds have been synthesized in both the series I and II. In series I, methoxy to n-pentyloxy derivatives are non mesogenic, n-hexyloxy to n-hexadecyloxy derivatives exhibit monotropic nematic mesophase. Smectic A mesophase commences from n-decyloxy derivatives as a monotropy and persist up to the last member synthesized. All the 12 compounds of series II exhibit mesomorphism. Methoxy to n-propyloxy derivatives exhibit monotropic nematic mesophse, and n-butyloxy to n-tetradecyloxy derivatives exhibit enantiotropic nematic mesophase. n-Hexayloxy to n-hexadecyloxy derivatives also exhibit enantiotropic smectic A mesophase. The mesomorphic properties of present series were compared with each other and with a structurally related mesogenic homologous series to evaluate the effects of central linkage on mesomorphism.