Alkoxy Derivatives Research Articles

A comparative theoretical study on the structural, spectral, microtopology exploration (ELF, RDG, IRI, TDM), NBO and nonlinear optical properties of Red170 from different solvents and substituents

The effect of solvents and substituents on the C.I. Pigment PR170, the best known member of the naphthol red family, is investigated. Both PR170 and its alkoxy derivatives were analyzed using FTIR, 1H NMR and UV–Vis spectroscopy. The study included the evaluation of the average local ionization energy (ALIE), MEP, HOMO-LUMO analysis. The nature of intra- and intermolecular contacts in the crystal structure was also investigated using crystal packing and Hirshfeld surface analysis. Covalent and non-covalent interactions in PR170 were comprehensively described by IRI, RDG and ELF. In addition, Natural Bonding Orbital (NBO) and Fukui function calculations were performed. An analysis of the UV–Vis electronic transitions for different solvents was carried out, providing insight into the charge transfer processes within both PR170 and its derivatives. In particular, the research indicated a CT-type excitation at the S2 level during the hole-electron transfer analysis. The NLO results showed that PR170 is a promising candidate for nonlinear optical materials.

Synthesis of Alkoxy Derivatives of Pyrrolo[3,4-c]pyridine-7-carbonitrile and Investigation of Their Application as Reagents for the Quantitative Determination of Mercury(II) Ions

Synthesis of Alkoxy Derivatives of Pyrrolo[3,4-c]pyridine-7-carbonitrile and Investigation of Their Application as Reagents for the Quantitative Determination of Mercury(II) Ions

Addition of alcohols to 4-methylene-1,3-dioxolanes

The addition of alcohols to 2-methylene-1,4-dioxaspiro[4.5]decane under the conditions of CF3CO2H catalysis occurs with the selective formation of the corresponding alkoxy derivatives. The conditions that ensure the preparative isolation of target compounds in 63-94% yields are determined, and the relative activity of alcohols in the addition reaction at the exocyclic double bond of substrates is determined.

Highly soluble germanium dioxide as a new source of germanium for derivatization with organic compounds

In modern germanium chemistry, toxic, corrosive and water- sensitive halogen and alkoxy derivatives, or poorly reactive polymeric dioxide are generally utilized. Recently developed highly water-soluble germanium dioxide was herein treated with diols and N-donor bases to produce novel highly reactive hydrophilic germanium source suitable for further derivatization.

Synthesis, antifungal studies, molecular docking, ADME and DNA interaction studies of 4-hydroxyphenyl benzothiazole linked 1,2,3-triazoles

In search of new bioactive 1,2,3-triazole hybrids, some 4-hydroxyphenyl benzothiazole (4-HBT) linked 1,2,3-triazole with varying lengths of alkyl spacers were synthesized from bromo alkoxy derivatives of 4-HBT. All the synthesized hybrids were satisfactorily characterized, and were evaluated for in-vitro antifungal activity against C. tropicalis and A. terreus fungal strains wherein compound 4 h showed better activity for both fungal strains compared to the reference drug Fluconazole. Molecular docking with the active site of 14α-sterol demethylase enzyme (PDBID: 1EA1) showed that all compounds exhibited strong H-bonding interactions with Thr260, Ala256, Arg96, Phe78, Leu321, Tyr76 while compound 4 h with the lone pair of -Cl have shown better interaction with the active site and were involved in H-bond interaction with THR 260. DNA binding study exhibited very good DNA-interaction (2.03 × 105 Lmol-1) of compound 4b with the hs-DNA. The results of DFT study and ADME investigations were accessed for the pharmacodynamics and pharmacokinetic properties of the synthesized molecules.

Reactions of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with alcohols

The reaction of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with alcohols and sodium alkoxides was evaluated under various conditions. Depending on the reaction conditions, either alkoxy or hydroxy derivatives of [1,2,5]thiadiazolo[3,4-d]pyridazine can be obtained. 4,7-Di-(dodecyloxy)- and 4,7-di(hexyloxy)[1,2,5]thiadiazolo[3,4-d]pyridazines, which may be of interest as the compounds exhibiting liquid crystalline properties, were synthesized for the first time.

Synthesis of 6- and 7-alkoxy-4-methylcoumarins from corresponding hydroxy coumarins and their conversion into 6- and 7-alkoxy-4-formylcoumarin derivatives

Hydroxy derivatives of 4-methyl-2H-chromen-2-one were prepared from hydroquinone and resorcinol through their reaction with ethyl acetoacetate. These hydroxy coumarins were then converted into corresponding alkoxy derivatives by reaction with alkyl halides. The yields of 6- and 7-alkoxy-4-methylcoumarins 3a–i and 4a–i were 55−95%. Oxidation of these compounds by selenium dioxide under conventional and microwave-assisted heating conditions produced corresponding 4-formyl compounds 5b–h and 6b–h with yields of 40−67% and 90−93%, respectively. Several 6- and 7-alkoxy-4-methylcoumarins 3a–i, 4a–i and nearly all 6- and 7-alkoxy-4-formylcoumarins 5b–h, 6b–h are novel compounds.

Crystal structures, Hirshfeld surface analysis and PIXEL calculations of four (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one derivatives, containing methoxy substituents. The importance of π interactions

A detailed structural analysis has been carried out on four chalcone (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one derivatives, having a varying number of methoxy substituents, namely (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one, (1), (E)-3-(4-methoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one, 2, (E)-3-(2,5-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one, 3, and (E)-3-(2,5-dimethoxyphenyl)-1-(2-hydroxy-3,4-dimethoxyphenyl)prop-2-en-1-one, 4. Crystal structures were determined at 100 K by single crystal X-ray diffraction. Compound 2 displayed an unexpectedly large interplanar angle of 25 and 28,o between the phenyl groups in the two independent molecules, due to the formation of a dimeric substructure requiring a pronounced phenyl group rotation to minimise steric hindrance. Such a substructure was absent in 1, 3 and 4. In all cases the 2-hydroxyl substituent forms intramolecular hydrogen bonds with its neighbouring carbonyl group. Different combinations of C–H⋯O, C–H···π and/or π ···π interactions are displayed by 1, 3 and 4, with also CO··· π intermolecular interactions present in 2. The relative contributions of various intermolecular contacts in these structures were investigated using Hirshfeld surfave analysis and the associated two dimensional fringerprint plots. Important molecule pairs were identified in the crystal structures using the PIXEL method. The PIXEL lattice energy calculations revealed that in all cases the dispersion contribution was the major contributor to the packing stabilization, followed by the Coulombic contribution.A search of structures of alkoxy derivatives of (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one derivatives in the CCDC data base has also been carried out.

The phenomenon of memory in vanadium ox nitride films

Vanadium oxides are representatives of a wide class of compounds possessing a metal-insulator phase transition. The properties of both the oxides themselves and their solid solutions with oxides of other metals have been well studied. The question of the possibility of dissolving nonmetallic components in the V-O system and its wobbling on the metal-insulator phase transition remain an open question. The solution of this problem, apart from the scientific side can also have practical significance: in spite of the wide possibilities and uses of vanadium oxides in optoelectronics, microwave technology and other fields, the need to search for materials with given temperatures of metal-insulator phase transition and electro-physical characteristics is obvious. In this paper, an attempt is made to dissolve nitrogen in vanadium dioxide films during their deposition by thermolysis of nitrogen-containing alkoxy derivatives.

Chemical Modification of Camelina Oil based Unsaturated Fatty Acid for Renewable Biolubricant Base Stock

A green and eco-friendly method for preparation of oleochemicals from Camelina oil was developed for possible application for bio-lubricant basestocks, The steps involved are consisting of epoxidation of Camelina oil based fatty acid followed by further branching with wide range of alcohol such as 2-propanol, n-butanol, isoamyl alcohol and 2-ethylhexanol. These products were evaluated with physico-chemical properties such as acid value, oxirane oxygen content (OOC), hydroxyl value, low temperature properties, viscosity at 40 and 100 °C, viscosity index and characterized by FTIR, 1H NMR. The appearance of peak at 824 cm–1 in the FTIR spectra was due to the formation of epoxy group and broad peak appeared at 3500-3300 cm–1 is for hydrogen bonded O-H stretching vibration of hydroxy group. The 1H NMR spectra showed a signal at 2.9-3.2 ppm region indicated CH-proton attached to the oxygen atom of the both epoxy group for epoxidized product, peaks for newly formed secondary alcohols emerged at 4.25-3.35 in alkoxy derivatives. The Camelina based synthetic product may find application in biolubricants base stock.

Systematic Modification of Zingerone Reveals Structural Requirements for Attraction of Jarvis\u2019s Fruit Fly

Tephritid fruit flies are amongst the most significant horticultural pests globally and male chemical lures are important for monitoring and control. Zingerone has emerged as a unique male fruit fly lure that can attract dacine fruit flies that are weakly or non-responsive to methyl eugenol and cuelure. However, the key features of zingerone that mediate this attraction are unknown. As Jarvis’s fruit fly, Bactrocera jarvisi (Tryon), is strongly attracted to zingerone, we evaluated the response of B. jarvisi to 37 zingerone analogues in a series of field trials to elucidate the functional groups involved in attraction. The most attractive analogues were alkoxy derivatives, with isopropoxy being the most attractive, followed by ethoxy and trifluoromethoxy analogues. All of the phenolic esters tested were also attractive with the response typically decreasing with increasing size of the ester. Results indicate that the carbonyl group, methoxy group, and phenol of zingerone are key sites for the attraction of B. jarvisi and identify some constraints on the range of structural modifications that can be made to zingerone without compromising attraction. These findings are important for future work in developing and optimising novel male chemical lures for fruit flies.

2,4,5-Tris(alkoxyaryl)imidazoline derivatives as potent scaffold for novel p53-MDM2 interaction inhibitors: Design, synthesis, and biological evaluation.

Imidazoline-based small molecule inhibitors of p53-MDM2 interaction intended for the treatment of p53 wild-type tumors are the promising structures for design of anticancer drugs. Based on fragment approach we have investigated a key role of substituents in cis-imidazoline core for biological activity of nutlin family compounds. Although the necessity of the substituents in the phenyl rings of cis-imidazoline has been shown, there are no studies in which the replacements of a halogen by other substituents have been investigated. A series of simple cis-imidazoline derivatives containing halogen, hydroxy and alkoxy-substituents were synthesized. The biological activity of the compounds was studied using assays of cytotoxicity (MTT) and p53 level. It was found that the hydroxyl-derivatives were not cytotoxic whereas the alkoxy analogues were the same or more active as halogen-substituted compounds in cell viability test. The synthesized alkoxy derivatives induced an increase of p53 level and did not promote necrotic cell death in the concentration up to 40 µM.

New Methods for the Synthesis of Alkoxy Derivatives of the closo-Decaborate Anion [2-B10H9(OR)]2–, Where R = C2H5, iso-C3H7, С4H9

A two-stage scheme was proposed for the synthesis of alkoxy derivatives of the closo-decaborate anion [B10H9(OR)]2–, where R = C2H5, iso-C3H7, C4H9. At the first stage, the oxonium derivatives with the general formula [B10H9(OR2)]– were synthesized by the reaction between the [B10H11]–anion and acyclic ethers. At the second stage, the synthesized oxonium derivatives reacted with hydrazine hydrate to form the alkoxy derivatives with the general formula [B10H9(OR)]2–, where R = C2H5, iso-C3H7, C4H9. This approach appreciably increased the yield of target products and simplified their separation. The alkoxy derivatives were separated and characterized by IR and 1H, 11B, and 13C NMR spectroscopy.

Liquid phase pyrolysis of wheat straw and poplar in hexadecane solvent

There is a need for replacement of fuel, especially transportation fuel, obtained from fossil resources by bio-based alternative. The thermochemical conversion is a feasible method to degrade and partially deoxygenate the natural resource lignocellulose to get bio-oils as fuel precursors. The present paper describes the liquid phase pyrolysis of wheat straw and poplar under inert atmosphere in n-hexadecane solvent. An autoclave batch reactor system was used. The influence of reaction temperature, residence time, solvent/biomass ratio and the effect of solid acid and base catalysts on the product distribution and yields were investigated. The reaction products were analyzed by means of CHNO elemental analysis, Solid Phase Micro Extraction-Gas Chromatograpy-Mass Spectroscopy (SPME-GC–MS), 1H and 13C-Nuclear Magnetic Resonance (NMR) spectroscopies. About 40–49 wt% of lignocellulosic carbon was successfully transferred to hexadecane. The best carbon yields were achieved at 350 °C. The main extracted products were alkyl and alkoxy derivatives of phenol and furan derivatives. By comparing seven parallel experiments in presence and absence of the catalysts no or only negligible catalytic effect was observed. The effect of heterogeneous catalysts was manifested only in splitting the primarily extracted macromolecules. The carbon/oxygen mass balances suggest that the extracted compounds have relatively high residual oxygen content.

Synthesis, electrochemical, thermal and photophysical characterization of quinoxaline-based π-extended electroluminescent heterocycles

This work describes the synthesis of two sets of photoactive compounds with π-extended conjugation developed from a quinoxaline core condensed from an ortho-diamine and 1,2-diketone and followed by a Sonogashira coupling reaction. The electrochemical, photophysical and thermal properties of these compounds were evaluated. Thermogravimetric analysis (TGA) indicated high thermal stability with decomposition temperatures up to 370 °C for all dyes. The electrochemical behaviour of the alkoxy and tetrazole quinoxaline derivatives showed a reversible wave in the reduction region because of the formation of radical anions and two irreversible oxidation waves at more positive potentials. The alkoxy and tetrazole compounds showed absorption in the blue region (∼460 nm) and in the violet region (∼430 nm), respectively, with molar absorptivity coefficients ascribed to allowed π–π* electronic transitions. The band-gaps of the alkoxy and tetrazole compounds were calculated by onset peaks presenting values of approximately 2.35 eV and 2.55 eV, respectively. A relative broad emission located at approximately 550 nm was observed for the alkoxy derivatives with a positive solvatochromism of ∼20 nm. A less intense solvatochromism was observed for the tetrazole derivatives; however, the maxima were located in the cyan-green to blue regions. The large Stokes' shift for all compounds (∼100 nm) probably indicates a charge transfer mechanism (ICT) in the excited state. The fluorescence lifetimes of both sets of compounds were obtained by time-correlated single photon counting (TCSPC) in different solvents, rendering nearly solvent-independent behaviour to the alkoxy derivatives but a pronounced solvatochromic effect to the tetrazoles, with one of the compounds dimerizing in the excited state. Because of the high electronic density of the molecular cores and good fluorescence quantum yields, a organic light emitting diode (OLED) of great colour purity was fabricated with one of the alkoxy derivatives. The diode was prepared by solution-based protocols offering 103 cd m−2 at 9.8 V with Comission Internationale de l’Eclairage (CIE) coordinates of (0.50, 0.50).

Synthesis of 8-alkoxy and 8,8′-dialkoxy derivatives of cobalt bis(dicarbollide)

In this paper, a simple and convenient way for synthesis of common alkoxy derivatives of cobalt bis(dicarbollide) was developed and a series of 8-alkoxy [8-RO-3,3′-Co(1,2-C2B9H10)(1,2-C2B9H11)]-, 8-alkoxy-8′-hydroxy [8-RO-8′-HO-3,3′-Co(1,2-C2B9H10)2]- and 8,8′-dialkoxy derivatives [8,8′-(RO)2-3,3′-Co(1,2-C2B9H10)2]- (R = Me, Et, Pr) were synthesized. The solid state structure of (Me4N)[8,8′-(MeO)2-3,3′-Co(1,2-C2B9H10)2] was determined by single crystal X-ray diffraction study.

Напівемпіричний аналіз взаємодії алкоксипохідних 1,4-бенздіазепіну з ГАМКа-рецептором на підставі даних молекулярного докінгу та фармакологічного ефекту

Introduction. Pharmacological spectrum of 1.4-benzodiazepine 3-alkoxy derivatives, in contrast to classical substances, has more prominent analgesic properties, but even among the synthesized and studied molecules there are compounds with different magnitude of this effect.The aim of the study – to evaluate the molecular docking parameters of the theoretically generated structures of 1.4-benzodiazepine alkoxy derivatives with the GABA receptor complex and to compare these data with the pharmacological activity of the synthesized compounds.The molecular docking procedure was carried out using the iGEMDOCK v2.1 program, optimized structures of already synthesized and theoretically designed molecules with differing substituents in the ortho position of the phenyl radical and the "7" position of the condensed system are generated in the Avogadro program (v 1.2.0). The average effective doses of compounds (penthylenetetrazole-induced seizures, 120 mg/kg, subcutaneously 30 min after compounds administration) were studied in white mice.The binding energy of all the generated structures is within the ranges of 81.6–96.8 kcal/mol. Virtual docking data analysis of substituted alkoxy derivatives allows identifying several binding sites inherent for 7-chloro- or 7-bromo-substituted benzodiazepine derivatives. The greatest influence on the binding of chlorine-substituted alkoxy derivatives have regions with a high polarity amino acids (16-23 D) and similar hydrophilicity and hydrophobicity. The contribution of Van der Waals and hydrogen interactions to the total binding energy is determined by the presence of halogen (chlorine or bromine). In penthylenetetrazole-induced seizures test the compounds containing the chlorophenyl substituent in the hetero ring were most active (ED50 (0.42±0.10) μmol/kg for the propyloxy derivative and (0.51±0.17) μmol/kg for the ethyloxy derivative) while for the compounds with the phenyl radical, the ED50 value were much higher (5.1±2.7) μmol/kg and (17.75±1.93) μmol/kg, respectively). The analgesic effect is mainly due to the lkoxy derivatives possibility of binding to a center containing residues of basic amino acids.

Photophysical characterization of hydroxy and ethoxy phenalenone derivatives

Phenalenone has been extensively studied due to its photophysical behavior. However, fewer are the articles referring to the phenalenone derivatives as singlet oxygen generators. The incorporation of substituents on the phenalenone ring rearranges the molecular electronic states changing its photophysical behavior. In order to rationalize the effect of the presence of electron-donor substituents on the phenalenone ring, we studied two ethoxy derivatives and their corresponding hydroxyl precursors. All derivatives prepared present smaller singlet oxygen quantum yield values than phenalenone. These lower quantum yields can be rationalized by considering non-radiative decay of singlet excited state absent in unsubstituted phenalenone. The hydroxy and alkoxy derivatives substituted in position 6 of phenalenone have larger fluorescence quantum yields than the ones substituted in position 3. Interestingly, 3-hydroxy-phenalenone shows a low emission quantum yield with two emission bands, which can be related with equilibria between diketo and enol tautomers in the first excited singlet state. Flash photolysis spectra for all derivatives were measured and the extinction coefficients of triplet–triplet absorption were evaluated near 500nm.

Photodimerization Kinetics of a Styrylquinoline Derivative in Langmuir–Blodgett Monolayers Monitored by Second Harmonic Generation

To explore the influence of surface packing densities on the interfacial photochemical kinetics, the surface-selective second harmonic generation (SHG) technique was used to investigate the kinetics of two-photon induced [2 + 2] photocycloadditions of a styrylquinoline alkoxy derivative within the Langmuir–Blodgett (LB) monolayers. The laser power dependence experiment revealed that this interfacial photodimerization is a first-order reaction, which implies that the photoexcitation is the rate-limiting step. Interestingly, a comparison of photodimerization kinetics at different surface packing densities shows a nonmonotonic distribution of reaction rate constants, which can be attributed to a result of combined effects of the topochemical mechanism and steric hindrance. The atomic force microscopy measurements and theoretical calculations were also employed to help understand the [2 + 2] photocycloaddition mechanisms. The results presented in this work demonstrate that the surface packing density plays an...

A Highly Potent Antibacterial Agent Targeting Methicillin-Resistant Staphylococcus aureus Based on Cobalt Bis(1,2-Dicarbollide) Alkoxy Derivative

Methicillin-resistant Staphylococcus aureus (MRSA) is a notorious superbug that is potentially life-threatening. Among conventional antibiotics, vancomycin is a “gold standard” agent used to treat serious MRSA infections. Such therapy, however, is often ineffective because of the emergence of less-susceptible strains. Therefore, the exploration of new antimicrobial agents, especially nonantibiotic drugs, to cope with the growing threat of MRSA has become an urgent necessity. Herein, we have investigated the possibility to develop a metallacarborane antimicrobial agent, cobalt bis(1,2-dicarbollide) alkoxy derivative (K121), and we have evaluated the relevant anti-MRSA behaviors. We demonstrated that K121 has a dose-dependent anti-MRSA activity with a low minimal inhibitory concentration of 8 μg/mL and a high selectivity over mammalian cells. In particular, a high bacteria-killing efficiency was observed with eradication of all MRSA cells within 30 min. In addition, K121 showed a high inhibition effect on t...