- Post‐modification of phthalocyanines via isocyanide-based multicomponent reactions: Highly dispersible peptidomimetic metallophthalocyanines as potent photosensitizers
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In this work, one-step synthesis of highly dispersible phthalocyanines containing carboxamide moieties via four-component Ugi reaction was demonstrated for the first time. These pseudopeptide-modified-phthalocyanines were characterized by means of IR, NMR, CHN and UV–Vis spectroscopy. Additionally, the purity of the pseudopeptide phthalocyanines was confirmed by capillary zone electrophoresis. Most of the synthesized phthalocyanines showed good dispersity in common organic solvents and especially in water. The in vitro photodynamic activities of water-soluble phthalocyanine 5k upon MCF-7 cancer cells were investigated and revealed that the cell viability was high in dark conditions, while the compound was phototoxic at visible light and the intensity of damage was directly related to its concentration. Also, phthalocyanine 5k showed high cellular uptake and more killing cells after the modification with Ugi-4CR. Since, many potent phthalocyanine photosensitizers are hydrophobic and poorly water-soluble, which limit their therapeutic applications, the novel phthalocyanines which modified through Ugi approach could be introduced as potent hydrophilic, nonaggregated and biocompatible sensitizers which can able to improve the effectiveness of photodynamic therapy.
- Afshari, Ronak,Ghasemi, Vahid,Shaabani, Shabnam,Shaabani, Ahmad,Aladaghlo, Zolfaghar,Fakhari, Ali Reza
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Read Online
- Compound herbicide based on dichloro quinolinic acid
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The invention discloses a compound herbicide based on quinclorac, which comprises 20 - 30 parts of quinclorac. Dichloromethane 3-8 parts, synergist 10 - 20 parts, wetting agent 1.5 - 4.5 parts, dispersing agent 1-3 parts, defoaming agent 0.5 - 2.5 parts and water 50 - 70 parts. The synergist inhibits the growth of cells by hindering the synthesis of the protein, and the sprouts of monocotyledonous plants are obtained through young buds of plants. The lower endoderm of the dicotyledonous plant is absorbed and conducted upwards, the seeds and roots absorb conduction, the absorption amount is low, the conduction speed is slow, the growth of young buds and roots is inhibited.
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Paragraph 0014; 0031; 0037; 0041; 0047; 0051; 0057
(2021/11/21)
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- Synthesis of new zinc(II) phthalocyanine conjugates with block copolymers for cancer therapy
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Synthetic routes towards new conjugates of hydrophilic zinc(II) phthalocyanine (ZnPc) with poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) (Pluronic P123) and poly(L-lactide) (PLLA), are described. The main semiproduct ZnPc was obtained by heating 4-nitrophthalimide with urea and zinc chloride, followed by the reduction step. Steglich esterification was used to synthesize two ZnPc-conjugated block copolymers, further utilized in fabrication of polymeric micelles (PMs) - functionalized with the zinc(II) phthalocyanine-type moiety. Biological evaluation of the PMs indicated an acceptable biocompatibility level in accord with requirements in the field of nanotheranostics and nanomedicine.
- Lamch, ?ukasz,Tsirigotis-Maniecka, Marta,Kulbacka, Julita,Wilk, Kazimiera A.
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supporting information
p. 433 - 445
(2021/02/03)
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- Clean production method 4 - nitrophthalimide
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The invention discloses a clean production method 4 -nitrophthalimide, which adopts 4 -nitrophthalic acid and urea to aminate in a solvent. A closed loop gives 4 -nitrophthalimide. The molar yield of the invention can reach above 85%. Product purity reaches 98% or more. After the reaction is finished, the reaction is cooled, the product is crystallized and precipitated, and the product is obtained through filtration. The filtered filtrate can be applied to the next batch without any treatment. To the method, the reaction substrate is changed, a new synthetic route is reconstructed, a large amount of waste acid due to nitration and acid mixing is avoided, the dangerous process of nitration reaction is avoided, the production management cost is reduced, and the production safety is greatly improved. , The production efficiency and the product quality are improved, and the cleanness of 4 -nitrophthalimide is realized. .
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Paragraph 0015-0025
(2021/09/15)
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- Azomethine phthalimides fluorescent E→Z photoswitches
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Herein, we report the synthesis and E→Z photoswitching behavior of two 4-substituted azomethine phthalimides containing anthracenyl and 4-(dimethylamino)phenyl moieties (EAMP1 and EAMP2). These compounds represent newly synthesized and unstudied photoswitches with dual fluorescence properties as E-isomers and at photostationary state (PSS) depending on the solvent polarity. Steady-state fluorescence measurements were performed in various solvents and the results show strong sensitivity on the environmental polarity. The kinetics of E→Z photoswitching to PSS was studied in AcCN by visible light activation at 410 nm (EAMP1) and long wavelength UV-light activation at 350 nm (EAMP2). The quantitative and qualitative performance of the switching behavior was evaluated by the degree of photoisomerization (R) and the rate constant (k). It was found for EAMP1 R = 6.95 %, k = 8.87 × 10?4 s?1 and EAMP2 R = 88.72 %, k = 4.00 × 10?4 s?1, respectively. The reason for the lower photoconversion of EAMP1 compared to the EAMP2 was analyzed through optimization of the molecular geometry of E- and Z-isomers in the ground state (S0) and first excited state (S1) by DFT/TD-DFT calculations with B3LYP/6-31+G(d,p) level of theory using IEFPCM in AcCN. It was found that E-isomers in the S0 have nonplanar conformation, while the Z-isomer of EAMP1 prefers twisted conformation and the Z-isomer of EAMP2 T-shaped conformation is energetically advantageous compared to the twisted one. The reason is the weak H….π noncovalent interaction (NCI) between 4-(dimethylamino)phenyl moiety and phthalimide ring. Moreover, the Z-isomer of EAMP2 is unusual stable up to 600 min at room temperature in dark compared to the EAMP1, which undergoes full Z→E relaxation for less than 60 min at the same conditions. The Z→E relaxation of EAMP2 is achieved for 90 min at 60 °C. The fluorescence E→Z switching behavior was studied by emission measurements in AcCN and 1,4-DOX as E-isomers and at PSS in room and liquid nitrogen (77 K) temperatures. In the polar and nonpolar solvents, red-shifted emissions with increased fluorescence quantum (Φfl) yields have been observed at PSS compared to the E-isomers. The molecular rotor behavior was studied in the binary mixture of glycerol:ethanol and the results show a sensitivity of the emission bands depending on the environmental viscosity. Time-resolved fluorescence decay measurements were performed in AcCN and 1,4-DOX as E-isomers and at PSS to estimate the mechanism of fundamental fluorescence bands. We found that dyes at PSS have longer lifetime (τ) compared to the E-isomers, especially in less polar 1,4-DOX.
- Georgiev, Anton,Yordanov, Dancho,Dimov, Deyan,Zhivkov, Ivailo,Nazarova, Dimana,Weiter, Martin
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- Indirect solvent assisted tautomerism in 4-substituted phthalimide 2-hydroxy-Schiff bases
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The paper presents the synthesis and characterization of two 4-substituted phthalimide 2-hydroxy-Schiff bases containing salicylic (4) and 2-hydroxy-1-naphthyl (5) moieties. The structural differences of 2-hydroxyaryl substituents, resulting in different enol/keto tautomeric behaviour, depending on the solvent environment were studied by absorption UV–Vis spectroscopy. Compound 5 is characterized by a solvent-dependent tautomeric equilibrium (KT in toluene = 0.12, acetonitrile = 0.22 and MeOH = 0.63) while no tautomerism is observed in 4. Ground state theoretical DFT calculations by using continuum solvation in MeOH indicate an energy barrier between enol/keto tautomer 5.6 kcal mol?1 of 4 and 0.63 kcal mol?1 of 5, which confirms the experimentally observed impossibility of the tautomeric equilibrium in the former. The experimentally observed specific solvent effect in methanol is modeled via explicit solvation. The excited state intramolecular proton transfer (ESIPT) was investigated by steady state fluorescence spectroscopy. Both compounds show a high rate of photoconversion to keto tautomers hence keto emissions with large Stokes shifts in five alcohols (MeOH, EtOH, 1-propanol, 1-butanol, and 1-pentanol) and various aprotic solvents (toluene, dichlormethane, acetone, AcCN). According to the excited state TDDFT calculations using implicit solvation in MeOH, it was found that enol tautomers of 4 and 5 are higher in energy compared to the keto ones, which explains the origin of the experimentally observed keto form emission.
- Antonov, Liudmil,Crochet, Aurelien,Deneva, Vera,Fromm, Katharina M.,Georgiev, Anton,Yordanov, Dancho
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- Palladium(II) phthalocyanines efficiently promote phosphine-free Sonogashira cross-coupling reaction at room temperature
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Herein we report that exceptionally simple and inexpensive Pd(II) complexes of phthalocyanines efficiently catalyze direct formation of diphenylacetylenes at ambient conditions with low loading of catalyst (0.5 mol%). Results of this study demonstrate that terminal alkynes reacted mildly with p-substituted aryl bromides at room temperature under Pd and Cu-cocatalysis to give the corresponding phenylacetylenes in yields up to 98%. Also we have examined this catalyst in Sonogashira cross-coupling with aryl chlorides and it was very effective and this reaction at room temperature that there is no examples in recent articles. This protocol represents the first use of palladium phthalocyanine as homogeneous catalyst in the Pd/Cu-promoted Sonogashira reaction. The palladium(II) phthalocyanine complex is significantly more active in Sonogashira cross-coupling between aryl halides and terminal alkynes as compared with traditional catalysts because of absence of palladium black formation through agglomeration of metal particles and deactivation of catalyst.
- Platonova, Yana B.,Tomilova, Larisa G.,Volov, Alexander N.
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p. 224 - 228
(2020/09/17)
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- Preparation of new biologically active and water soluble dyes: Characterization, aggregation and extraction of metal ions from solutions
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The synthesis of metallo-phthalocyanines complexes (M = Co, Ni, Cu, Zn) containing azo dye were described in this study. The metallophthalocyanines have been supported by elemental analysis, UV-visible, FT-IR and NMR. The aggregation of phthalocyanine compounds was investigated in different solvents and concentrations. The newly synthesized metallophthalocyanines possess modest antibacterial activity against various Gram-positive and Gram-negative bacteria. Moreover, these complexes have been tested as antioxidant and presented remarkable activities by two different in vitro chemical assays. They were able to reduce DPPH % radical with IC50 values ranging from 3.8 to 7.5 μmol L-1 and some of them also reduced ABTS % radical cation.
- Touj, Nedra,Al-Ayed, Abdullah Sulaiman,Hamdi, Naceur
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p. 1398 - 1404
(2019/06/10)
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- Synthesizing method of 5-fluoro-3-methyl isobenzofuran-1(3H)-ketone
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The invention relates to the technical field of medicine and relates to a synthesizing method of 5-fluoro-3-methyl isobenzofuran-1(3H)-ketone. The 5-fluoro-3-methyl isobenzofuran-1(3H)-ketone is synthesized by subjecting the initial raw material phthalimide to 8 steps such as nitration, reduction, cyclizing, diazotization, bromination and esterification. The method has the advantages that the preparation of the 5-fluoro-3-methyl isobenzofuran-1(3H)-ketone which is the key intermediate of the antitumor drug Lorlatinib (PF-06463922), total yield can reach 7.0% or above, and the method is simpleto operate, convenient in post-processing, low in time consumption, low in cost and beneficial to industrialization; the Lorlatinib is synthesized by subjecting the intermediate and 1-methyl-3-(( methylamino)methyl)-1H-pyrazol-5-nitrile to ammonolysis, substitution, coupling, chiral resolution and the like, and a new method is provided for the synthesizing of the antitumor drug Lorlatinib.
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Paragraph 0039-0042
(2019/01/23)
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- Development of three ways molecular logic gate based on water soluble phenazine fluorescent ‘selective ion’ sensor
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New hydrophilic fluorescent selective ion sensor based on phenazine and phthalazine moieties, 1,1′-(phenazine-2,3-diyl)-bis(3-(1,4-dihydroxyphthalazin-6-yl)urea) (1), has been designed, synthesized and characterized. Interestingly, sensor 1 exhibits prominent “turn-on” and “turn-off” fluorogenic signaling at 580 nm towards Fe2+ & AcO? and Sr2+ & Cu2+, respectively. The fluorescence titration experiments shed light on the nature of the interaction between 1 and guest molecules (Fe2+, Sr2+, Cu2+ and AcO?), which divulge that 1 is flexible enough to orient itself according to the size of the guest molecule. Water mediated excited-state intramolecular proton transfer (ESIPT) and photo-induced electron transfer (PET) mechanisms are responsible for the dual behavior of 1, which binds with guest molecules in 1:1 stoichiometry. Based on the significant duplex fluorescence response of 1, a molecular logic gate keypad lock with sixteen “on” passwords for a storage system has been developed.
- Daniel Thangadurai,Nithya,Rakkiyanasamy
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supporting information
p. 132 - 140
(2018/12/13)
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- Novel n-channel organic semiconductor based on pyrene-phenazine fused monoimide and bisimides
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Large π-conjugated pyrene-phenazine monoimide and bisimides were synthesized by imine condensation reaction. These imides form well ordered 1D nanotapes upon self-assembly in solution. Electrochemical and electric conductivity measurement reveal it can be served as an n-channel semiconductor with large charge carrier mobility up to 4.1 cm2 V?1 s?1. Both alkylated imides are highly luminescent, and can be quenched via protonization using trifluoroacetic acid, which could be served as potential colorimetric acid sensors.
- Song, Xiaoyu,Zhao, Jing,Zhang, Wandong,Chen, Long
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supporting information
p. 331 - 335
(2017/10/17)
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- Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions
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Imidation of various anhydrides employing solvent-free grindstone technique using smectite clays as recyclable and green catalysts was examined and obtained excellent yields.
- Marvi, Omid
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p. 3501 - 3504
(2017/08/14)
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- Synthesis of phthalimide disperse dyes and study on the interaction energy
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Three azo dyes had been synthesized using N-ethyl substituted, dibromo-substituted and dicyano-substituted phthalimides as diazo components. All of the synthesized intermediates and dyes have been characterized by MS, 1H NMR, IR and elemental analyses. The dyeing behavior and fastness properties of these dyes have been investigated. Modeling the interaction energy of benzene-benzene, phthalimide-benzene and phthalimide-phthalimide rings, molecule optimization and the interaction energy researching have been done with density functional theory ωB97XD, 6-311G++(d,p) basis set. The results showed that: phthalimide molecule has better coplanarity. Molecule energy of benzene-benzene, phthalimide-benzene and phthalimide-phthalimide rings decreased first and then increased with the increase of the distance between the rings, the lowest energy happened when the distance was about 3.5 ?. Electrostatic force affected the interaction energy most. Substituent groups mainly altered the dispersion force and reduced the energy of the system. The optimization interaction energy of phthalimide-phthalimide, phthalimide-benzene and benzene-benzene was ?47.78 kJ/mol, ?34.66 kJ/mol and ?17.59 kJ/mol. Substituted dibromo group reduced the dipole interaction of the dye.
- Zhan, Yizhen,Zhao, Xue,Wang, Wei
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p. 240 - 250
(2017/07/17)
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- Isoindol - 1, 3 - dione compound and its preparation method and application (by machine translation)
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The invention discloses a isoindole - 1, 3 - dione compound and its preparation method and application. The general formula (I) has the structure shown. The invention of the isoindole - 1, 3 - diones to LNCap cells with cell inhibitory activity, can be used for preparing anti-tumor drug. (by machine translation)
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Paragraph 0067-0069
(2017/08/02)
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- Synthesis method of phthalimide and phenyl ring-substituted phthalimide derivative
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The invention provides a synthesis method of phthalimide and a phenyl ring-substituted phthalimide derivative. The synthesis method comprises that aromatic ketone and ammonia gas or an ammonia gas precursor as substrates and air or oxygen as an oxygen source undergo a reaction under catalyst action and liquid phase conditions to produce phthalimide and a phenyl ring-substituted phthalimide derivative. The synthesis method is mild, realizes high oxidation efficiency and a high product yield, utilizes oxygen or air as an oxygen source, is economic and eco-friendly and has a good application prospect.
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Paragraph 0013; 0017; 0018; 0020; 0024; 0028
(2017/08/25)
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- Luminol or isoluminol synthesizing method by one-pot process
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The invention discloses a luminol or isoluminol synthesizing method by a one-pot process. The luminol or the isoluminol synthesizing method by the one-pot process includes the steps of 1) enabling 3-nitrophthalic acid or 4-nitrophthalic acid as a starting material to react with urea in an organic solvent to obtain 3-nitrophthalimide or 4-nitrophthalimide; 2) enabling the 3-nitrophthalimide or the 4-nitrophthalimide to react with a hydrazine hydrate aqueous solution to obtain 3-nitrophthalhydrazide or 4-nitrophthalhydrazide; 3) enabling the 3-nitrophthalhydrazide or the 4-nitrophthalhydrazide to react with a reducing agent in the presence of a catalyst to obtain luminol or isoluminol. The luminol or the isoluminol synthesizing method by the one-pot process has the advantages of simplicity, convenience in operation, low cost, high yield and less pollution, and can be applicable to industrialized production.
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Paragraph 0048
(2017/08/30)
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- New anthracene-based-phtalocyanine semi-conducting materials: Synthesis and optoelectronic properties
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A new anthracene-based semi-conducting phtalocyanines AnPc and AnPc-Tr were synthesized in solvent-free conditions. The supramolecular structure of these compounds was confirmed by NMR and FT-IR spectroscopies. Their optical properties were investigated by UV-vis and photoluminescence spectroscopies. The optical gaps were estimated from the absorption-onsets films, and the obtained values were of 1.50 eV and 1.47 eV for AnPc-Tr and AnPc respectively. In solid state, a weaker π-π-interactions of conjugated systems were obtained in the case of AnPc-Tr in comparison with AnPc. This behavior was explained by steric hindrance of triazol groups, which decrease the planarity of macromolecular structure. The HOMO and LUMO levels were estimated using cyclic voltammetry analysis; two phtalocyanine derivatives show a comparable ionization potential. The phtalacyanine containing triazole groups (AnPc-Tr) reveals a higher electron affinity in comparison with AnPc. Single-layer diode devices were fabricated and showed relatively low turn-on voltages.
- Kahouech,Hriz,Touaiti,Bassem
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p. 144 - 154
(2015/12/12)
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- Isoindole-1,3-dione derivatives as RSK2 inhibitors: Synthesis, molecular docking simulation and SAR analysis
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RSK2 (p90 ribosomal S6 kinase 2) is a serine/threonine kinase expressed in a variety of cancers. Molecular-targeted inhibition of RSK2 as a potential therapeutic strategy for human cancers has been documented. In this work, a series of isoindole-1,3-dione derivatives as novel RSK2 inhibitors were designed and synthesized from a hit discovered in our previous study. Some compounds were confirmed to be moderately potent RSK2 inhibitors with IC50 values of about 0.5 μM. Structure-activity relationship analysis and binding mode studies by molecular docking were performed.
- Zhou, Wei,Li, Shiliang,Lu, Weiqiang,Yuan, Jun,Xu, Yufang,Li, Honglin,Huang, Jin,Zhao, Zhenjiang
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supporting information
p. 292 - 296
(2016/03/01)
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- Synthesis of new zinc(II) phthalocyanine conjugates with block copolymers for cancer therapy
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Synthetic routes towards new conjugates of hydrophilic zinc(II) phthalocyanine (ZnPc) with poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide) (Pluronic P123) and poly(L-lactide) (PLLA), are described. The main semiproduct ZnPc was obtained by heating 4-nitrophthalimide with urea and zinc chloride, followed by the reduction step. Steglich esterification was used to synthesize two ZnPc-conjugated block copolymers, further utilized in fabrication of polymeric micelles (PMs)-functionalized with the zinc(II) phthalocyanine-type moiety. Biological evaluation of the PMs indicated an acceptable biocompatibility level in accord with requirements in the field of nanotheranostics and nanomedicine.
- Lamch, Lukasz,Tsirigotis-Maniecka, Marta,Kulbacka, Julita,Wilk, Kazimiera A.
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p. 433 - 445
(2017/03/09)
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- Preparation method of high yield isoluminol luminescent reagent
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The invention discloses a preparation method of a high yield isoluminol luminescent reagent. According to the method, the step (1) adopts a microwave preparation method, the reaction time is 5min, and the microwave method can speed up reaction, in step (2), when first pumping filtration of the reaction solution ends, the product is taken out and put into 0.2kg of ice water to conduct stirring and pumping filtration, washing and pumping filtration are carried out repeatedly 4 times, and repeated pumping washing can improve the product purity, a 4-nitrophthalimide product of the step (2) is finally subjected to recrystallization with 300mL of analytically pure, i.e. anhydrous ethanol so as to obtain a refined product, use of the ethanol as the extracting agent can improve the product purity, the hydrazine hydrate used in step (3) has purity of 85%, and the purity of ordinary industrial hydrazine hydrate is 40-80%, by using higher purity hydrazine hydrate in the invention, the product yield can be increased, and the cooling temperature of step (4) is -3DEG C, the product can crystallize rapidly under the temperature, thus ensuring the purity and yield of the product.
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Paragraph 0034; 0035
(2017/06/02)
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- Novel aqueous soluble cobalt(II) phthalocyanines of tetracarboxyl-substituted: Synthesis and catalytic activity on oxidation of sodium diethyldithiocarbamate
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Enhancement of the catalytic activity of phthalocyanine catalysts by immobilizing them on polymer matrix has been studied. It has been found that the immobilization of cobalt(II) phthalocyanines on polymers enhances their catalytic activity in the oxidation of sodium diethyldithiocarbamate by air oxygen under mild conditions.
- Vashurin, Artur,Maizlish, Vladimir,Pukhovskaya, Svetlana,Voronina, Alena,Kuzmin, Ilya,Futerman, Natalya,Golubchikov, Oleg,Koifman, Oskar
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p. 573 - 581
(2015/05/05)
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- Design, synthesis and structure-activity relationship studies of morpholino-1H-phenalene derivatives that antagonize Mcl-1/Bcl-2
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We report herein characteristic studies of Mcl-1 and Bcl-2 dual inhibitors. It was found that a protruding carbonyl group forming hydrogen bond with R263 plays a predominant role compared with the hydrophobic group that occupies the p2 pocket. A series of dual inhibitors representing different parts of the morpholino-1H-phenalene were designed, synthesized and evaluated.
- Li, Xiangqian,Liang, Xiaomeng,Song, Ting,Su, Pengchen,Zhang, Zhichao
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p. 5738 - 5746
(2015/02/02)
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- A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors
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Several members of a new family of non-sugar-type α-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast α-glycosidase and rat intestinal α-glycosidase. Almost all the compounds had strong inhibitory activities against yeast α-glycosidase. Regarding rat intestinal α-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal α-amylase. Structure-activity relationship studies indicated that 5-(p- toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the α-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities.
- Bian, Xiaoli,Wang, Qian,Ke, Changhu,Zhao, Guilan,Li, Yiping
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p. 2022 - 2026
(2013/04/24)
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- Synthesis and evaluation of antibacterial activity of water-soluble copper, nickel and zinc tetra (n-carbonylacrylic) aminephthalocyanines
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Water-soluble copper, nickel, and zinc tetra (n-carbonylacrylic) aminephthalocyanines were synthesized with an aim to evaluate their role as therapeutic materials. They were characterized by UV-Vis spectrophotometer, infra-red spectra, elemental analysis, nuclear magnetic resonance, and thermogravimetry. Efforts were made to optimize the synthesis of intermediates and final products. Photoluminescence studies were carried out on these compounds. The investigation of antibacterial activity of these aqueous soluble phthalocyanines was carried out on Staphylococcus citreus, Serratia marcescens, Proteus vulgaris, Bacillus subtilis, and Pseudomonas fluorescence, showed good inhibitory activity.
- Pavaskar,Patil,Furtado,Salker
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p. 4300 - 4307
(2013/09/02)
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- The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives
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The synthesis and biological evaluation of a series of novel isobenzofuran-based compounds are described. The compounds were evaluated for their immunosuppressive effects of T-cell proliferation and IMPDH type II inhibitor activity in vitro, as well as their structure-activity relationships were assessed. Several compounds demonstrated highly efficacious immunosuppressive properties, especially compounds 2d, 2e, 2h and 2j, which were superior to MPA, while compounds 2k, 2m, 2n, 4c and 5d exhibited an equipotent inhibitory activity compared to MPA. Generally, it was obviously demonstrated that α,β-unsaturated amides proved more potent than the diamide and urea series. The present study provides a guide for further research on development of safe and effective immunosuppressive agents.
- Yang, Na,Wang, Qing-He,Wang, Wen-Qian,Wang, Jian,Li, Feng,Tan, Shen-Peng,Cheng, Mao-Sheng
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scheme or table
p. 53 - 56
(2012/02/16)
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- First observation of tetranitro iron (II) phthalocyanine catalyzed oxidation of phenolic pollutant assisted with 4-aminoantipyrine using dioxygen as oxidant
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A novel system for catalytic oxidation of phenol and chlorophenol pollutant in water by tetranitro iron (II) phthalocyanine (TNFe(II)Pc) is reported for the first time. In this system, several phenolic substrates (phenol, 2-chlorophenol, 4-chlorophenol and 2,4-dichlorophenol) could be easily oxidized by naturally dissolved oxygen in the presence of TNFe(II)Pc, and then rapidly combined with 4-aminoantipyrine to generate the pink dye. The catalytic oxidation process and resulting products were monitored by UV-Vis spectroscopy and high performance liquid chromatography-mass spectrometer (HPLC-MS) technique. Control experiments demonstrated that the generation of superoxide anion radical was crucial for the dye formation, and a possible mechanism involved a successive single electron transfer from phenolic substrates to O2 via the axis of TNFe(II)Pc was proposed. Potentially, this system is promising for application in chromogenic identification of phenolic pollutant. Crown Copyright
- Li, Dapeng,Tong, Yilin,Huang, Jun,Ding, Liyun,Zhong, Yunming,Zeng, Dan,Yan, Ping
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experimental part
p. 108 - 116
(2011/10/05)
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- LIGHT-DRIVEN ROTARY MOLECULAR MOTORS
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Compounds of Formula (1) are disclosed. Cb is a carbocyclic or heterocyclic group having an atom within the cyclic structure selected from C, N, Si, and Cr and singly bound to A. A is CR, COR, CSR, CNR2, CCN, CCONR2, CNO2, CNNAr, CX′, or N. Cr is a chromophore having a substantially planar cyclic structure. The compounds function as nanometer-scale rotary molecular motors powered and controlled by light energy. The design of the molecular motor devices is flexible so that the rotary direction, drive light wavelength, and other physical characteristics can be varied. The compounds can be chemically functionalized to allow it to be integrated into or attached to a variety of structures. The device can be used in applications where mechanical power, positional control, and information encoding are to be generated at the size scale of individual molecules.
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Page/Page column 15
(2011/04/19)
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- Synthesis of some nitrogen mustards (Mannich bases)
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Several Mannich base half nitrogen mustards have been synthesised by the condensation of 3-substituted phthalimides and 4-substituted phthalimides with (2-chloroethyl) amine in ethanol- formalin.
- Sinha, Girish Kumar,Mehra,Kumar, Sharad
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experimental part
p. 1261 - 1264
(2012/04/04)
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- Colorimetric detection of achiral anions and chiral carboxylates by a chiral thiourea-phthalimide dyad
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The chiral chemosensor 1, based on a thiourea-activated phthalimide, is available by four reaction steps from 4-nitrophthalimide. 1 detects fluoride, chloride, acetate, and dihydrogen phosphate anions by changes in UV-vis absorption. Fluoride in excess induces deprotonation whereas the other anions show only complex formation in the ground state. 1H-NMR studies confirm the formation of these H-bonded complexes and the fluoride-induced receptor deprotonation in the recognition process. Moderate chiral recognition was observed for sodium d/l-lactate with Kass(d)/Kass(l) = 1.93.
- Griesbeck, Axel G.,Hanft, Sebastian,Diaz Miara, Yrene
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experimental part
p. 1385 - 1390
(2011/11/14)
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- Self-assembly of phthalocyanine and polyacrylic acid composite multilayers on cellulose nanofibers
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In this study, a novel nanocomposite multilayers was deposited on the electrospun nanofibrous mats by an electrostatic layer-by-layer (LBL) self-assembly technique. The positively charged water-insoluble 2,9,16,23-tetraaminophthalocyanine copper (CuTaPc) and the negatively charged water-soluble poly(acrylic acid) (PAA) were alternately deposited on the surface of negatively charged nanofibrous cellulose mats. The cationic CuTaPc was synthesized and characterized by UV-Vis and Fourier transform infrared (FT-IR) spectroscopy. The template nanofibrous cellulose mats were obtained from the alkaline hydrolysis of electrospun nanofibrous cellulose acetate mats. The resultant nanofibrous mats were characterized by scanning electron microscopy (SEM) and FT-IR spectroscopy. The SEM images showed that the composite LBL structured films were homogeneously deposited on the surface of the nanofibers. The diameters of nanofibers increased with the number of deposition bilayers. The average thickness of each CuTaPc/PAA bilayer is about 10 nm. Additionally, the FT-IR spectra results also indicated that the CuTaPc and PAA were coated on the nanofibrous cellulose mats.
- Mao, Xue,Ding, Bin,Wang, Moran,Yin, Yanbing
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scheme or table
p. 839 - 844
(2011/11/06)
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- Unexpected reduction of N-hydroxyphthalimides to phthalimides-orthogonal reduction of functionalized N-hydroxyphthalimides
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A chemoselective reduction of N-hydroxyphthalimides to phthalimides under mild conditions has been discovered. It involves reaction of an N-hydroxyimide with bis(pinacolato)diboron in the presence of a base. Other easily reducible functional groups, such as iodo, nitro, or azido groups are unaffected. Alternatively, such functional groups may be selectively reduced without affecting the N-hydroxyimide moiety using a set of classical conditions. Georg Thieme Verlag Stuttgart - New York.
- Jacq, Jér?me,Berthiol, Florian,Einhorn, Cathy,Einhorn, Jacques
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body text
p. 2263 - 2266
(2010/11/24)
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- CHEMICAL COMPOUNDS
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The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
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- Formamide, a novel challenging reagent for the direct synthesis of non-N-substituted cyclic imides
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Aliphatic and aromatic cyclic imides have been prepared in high to moderate yields from cyclic carboxylic anhydrides or corresponding dicarboxylic acids, using formamide as reagent at 170-180°C for 5-6 hours. In the case of aromatic products with lower solubility in formamide, we used N-methyl-2-pyrrolidinone (NMP) as supplementary solvent, which facilitates the reaction.
- Chiriac, Constantin I.,Nechifor, Marioara,Tanasǎ, Fulga
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p. 883 - 886
(2008/09/20)
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- Guanidino substituted isoindolones as novel glycoprotein IIb-IIIa receptor antagonists
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Design and synthesis of a novel potent glycoprotein IIb-IIIa (GP IIb-IIIa) receptor antagonist based on isoindolone skeleton has been described. This scaffold has been derived from earlier reported pseudopeptides. Synthesis by a novel route has been achieved. Few molecules show very potent in vitro activity. Further identification of probable additional hydrogen bond donor site has been described.
- Lal, Bansi,Gangopadhyay, Ashok K.,Jagtap,Tanpure, Rajendra,Rao,Gupte, Ravindra D.,Subbarayan,Asudani, Gope
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p. 1815 - 1832
(2008/09/18)
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- Rapid and convenient microwave-assisted synthesis of aromatic imides and N-hydroxymethylimides
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Extremely simple high-yielding and rapid microwave-assisted synthesis of wide array of aromatic mono and diimides and mono- and bis-N-hydroxymethylimides is reported.
- Kacprzak, Karol
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p. 1499 - 1507
(2007/10/03)
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- Preparation of 1,2-bis(3,4-dicyanophenoxymethyl)benzene and the binuclear zinc phthalocyanine derived from it
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A method of synthesis of 1,2-bis(3,4-dicyanophenoxymethyl)benzene from the 1,2-bis(hydroxymethyl)benzene and 4-nitrophthalodinitrile is developed. Its tetramerization with Zn(OAc)2·2H2O gives a binuclear zinc phthalocyanine of a new type, containing four o-phenylidene bridges. The use of microwave heating decreases reaction time and increases yield.
- Tolbin, Alexander Yu.,Ivanov, Alexey V.,Tomilova, Larisa G.,Zefirov, Nikolai S.
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- Synthesis and structure/property correlation of fully functionalized photorefractive polymers
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This paper describes the synthesis and physical study of several new photorefractive polymers. The Heck reaction was successfully applied in the synthesis of these multifunctional polymers. These polymers are conjugated poly(phenylenevinylene)s copolymerized with a small amount of macrocyclic zinc complexes as the photosensitizers. Nonlinear optical chromophores were incorporated as the pendant groups. Both electron-rich and electron-deficient PPV backbones were synthesized. Experimental results showed that when an electron-rich photosensitizer is used, the electron-deficient component for charge transport (CN-PPV) enhances photorefractive performance and reduces the response time.
- You, Wei,Wang, Liming,Wang, Qing,Yu, Luping
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p. 4636 - 4645
(2007/10/03)
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- Imidation of cyclic carboxylic anhydrides under microwave irradiation
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Efficient and facile conversion of cyclic carboxylic anhydrides to corresponding imides with formamide under microwave irradiation is described.
- Peng,Song,Qian
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p. 1927 - 1931
(2007/10/03)
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- An application of the stille coupling for the preparation of arylated phthalonitriles and phthalocyanines
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The substituted phthalonitriles 4-phenylphthalonitrile (2a), 4-(2,5-dimethoxyphenyl)phthalonitrile (2b) and 2-(3,4-dicyanophenyl)-4-methylpyridine (2c) have been prepared in good yields from 4-iodophthalonitrile 3, the synthesis of which is also discussed, using the Stille coupling method. Such phthalonitriles are precursors for phthalocyanines with the possibility of biphenyl-like orientation of a peripheral substituent with respect to the macrocycle ring plane. As an example, 2b was used in the preparation of tetra(dimethoxyphenyl)phthalocyanine 1a. Both 1a and the corresponding zinc(II) complex show good solubility in non-polar solvents such as dichloromethane.
- Aranyos, Viviane,Castano, Ana M.,Grennberg, Helena
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p. 714 - 720
(2007/10/03)
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- A concise, regio and stereoselective route to fluorinated protoberberines via tandem addition-cyclisation reactions of phthalide anions with 3,4-dihydroisoquinolines
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A series of fluorinated protoberberines have been prepared by condensing fluorinated phthalide anions with 6,7-dimethoxydihydroisoquinoline. The spectroscopy and stereochemistry of the products are discussed and the stereochemical outcome of the reactions rationalised.
- Warrener, Ronald N.,Liu, Ligong,Russell, Richard A.
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p. 7485 - 7496
(2007/10/03)
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- Gas adsorption and gas-sensing properties of europium bisphthalocyanine derivative Langmuir-Blodgett thin films
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In this paper, europium bisphthalocyanine derivative (EuPc′2) LB films transferred to an interdigital electrode have been prepared at room temperature. The dynamic response of the electrical conductance to Cl2 gas is presented. At room temperature, the response time of 10-layer LB films of EuPc′2 is 45 s and the recovery time is 1 min after exposure to a concentration of 50 ppm Cl2. The reproducibility of the conductivity changes can be improved by using pulsed operation to reduce the exposure time to Cl2. The change in film conductivity upon exposure of different concentrations of Cl2 gas has been measured. The lowest detectable concentration of Cl2 gas is 2 ppm. The maximum conductance change varies linearly with film thickness. The response time constants also increase with film thickness. The interaction between EuPc′2 and Cl2 in the LB films was monitored by UV-vis spectroscopy. LB films exposed to Cl2 gave a red-shifted Q-band which can be predicted from the conductance data.
- Liang,Gan,Yuan,Wei
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- Synthesis and Spectral Properties of Substituted meso-Tetraphenyltetrabenzoporphins and Their Metal Complexes
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Previously unknown phenyl-, nitro-, and amino-substituted meso-tetraphenyltetrabenzoporphins and their complexes with Zn2+, In3+, and Sn4+ were prepared, and the spectral characteristics were studied. The influence of substitution and the nature of the central metal ion on the properties of the new pigments was examined.
- Galanin,Kudrik,Shaposhnikov
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p. 1306 - 1309
(2007/10/03)
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- Synthesis and anticonvulsant activity of some N-phenylphthalimides
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The anticonvulsant potential of a series of N-phenylphthalimide derivatives has been screened in subcutaneous pentylenetetrazole seizure (scPTZ) and maximal electroshock seizure (MES) tests. Intraperitoneal 4-amino-N-phenylphthalimides were the most potent agents against MES in mice. Referring to the N-(2,6-dimethylphenyl)phthalimide structure, the order of anticonvulsant activity appears to correspond to the phthalimide ring substitution pattern of 4-amino > 4-nitro > 4-methyl; H > 3-nitro; 3-amino. The 4-amino-N-(2-methylphenyl)phthalimide displays an anti-MES ED50 of 47.61 μmol/kg with a protective index (PI) of 4.2. Oral administration to rats of the compounds found to be active in mice showed that the 4-amino-N-(2,6-dimethylphenyl)phthalimide is the most potent anti-MES agent in rats, exhibiting an ED50 of 25.2 μmol/kg and a PI greater than 75. Regarding the nature of the 2 and 6 substituents of the N-phenyl ring, the anticonvulsant efficiencies may be ordered as follows: 2,6-dimethyl > 2-methyl > 2-ethyl > 2-ethyl-6-methyl > 2,6-diethyl > unsubstituted phenyl ring. N-Phenylphthalimide derivatives seem to have great potential as candidate anticonvulsant drugs.
- Bailleux,Vallee,Nuyts,Vamecq
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p. 1817 - 1821
(2007/10/02)
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- Determination of the Molecular Orientation of a Phthalocyanine Derivative in a Langmuir-Blodgett Film by Polarized UV-VIS Spectra
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Langmuir-Blodgett (LB) films of (p-carboxyphenoxy)-tri(2,4-di-tert-pentyl phenoxy)phthalocyanine copper(II) (asyCuPc) are prepared; the associated forms of the compound in chloroform solution and the particular orientation of asyCuPc molecular macrocycles in LB films is determined by polarized UV-VIS.
- Yan, Wang,Zhou, Yuqing,Wang, Xinping,Chen, Wenqi,Xi, Shiquan
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p. 873 - 875
(2007/10/02)
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- Synthesis and Characterization of Di-disubstituted Phthalocyanines
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An improved approach to the synthesis of di-disubstituted phthalocyanines from two different phthalyl precursors is described.The method combines substituted 1,3-diiminoisoindoles and 6/7-nitro-1,3,3-trichloroisoindolenine to synthesize phthalocyanine.The method can be applied to the synthesis of hydrogen and metallo phthalocyanine.The yields are variable, ranging from 17percent to 72percent depending on the substituents.
- Young, Joseph G.,Onyebuagu, William
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p. 2155 - 2159
(2007/10/02)
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- REACTION OF 4-NITROPHTHALONITRILE WITH CARBONATE, NITRITE, AND FLUORIDE
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In DMSO and DMF at elevated temperatures, KF, KNO2, NaNO2, K2CO3, and Na2CO3 react with 4-nitrophthalonitrile to form 4,4'-oxybis(phthalonitrile) and, mostly, 4-hydroxyphthalonitrile.Formation ratios depend on reaction conditions.Intermediates are discussed.
- Woehrle, Dieter,Knothe, Gerhard
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p. 3231 - 3240
(2007/10/02)
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- Kinetic and equilibrium in the ammonolysis of substituted phthalimides
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Kinetic studies are reported for the base hydrolysis to phthalamic acid anions (H) and ammonolysis to phthalamides (A) for seven phthalimides (P): 1, unsubstituted; 2, 4-NO2; 3, 4-Cl; 4, 4-tBu; 5, 3-NO2; 6, 3-Me; 7, 3-Me3Si.The hydrolysis kinetics require two mechanisms, one which is first order in neutral imide and first order in hydroxide ion, and a second, which is important only in quite concentrated NaOH, which is first order in neutral phthalimide and second order in hydroxide ion.Ammonolysis kinetics for 1-5 revealed the rate law: Rate = kN ->.A mechanism is proposed with rate-determining breakdown of the anionic form of the tetrahedral intermediate derived by addition of NH3 to the phthalimide.The ammonolysis is reversible.The phthalamide hydrolyzes to the phthalamic acid via cyclization to an intermediate phthalimide, which is detected in concentrated base where its formation from phthalamide is more rapid than its subsequent hydrolysis.Rate constants for the cyclization follow the rate law: Rate = kcyc ->.This reaction is the microscopic reverse of the ammonolysis, and the ratio kN/kcyc provides the equilibrium constant Keq for the reaction P + NH3 = A.Values for 1-5 lie in the range 2 x 102 - 4 x 103.With 3-methylphthalimide, kinetics in aqueous ammonia do not obey a first-order relationship, but they could be analyzed by a scheme whereby the phthalimide is converted reversibly to the phthalamide and simultaneously undergoes an irreversible hydrolysis.The value of Keq in the system is 1.8.With 3-trimethylsilylphthalimide the value of Keq is further reduced to 0.01.The ammonolysis reaction does occur more quickly than hydrolysis but the equilibrium is so unfavorable that even in concentrated ammonia only a small amount of the phthalamide is ever formed.
- McClelland, Robert A.,Seaman, N. Esther,Duff, James M.,Branston, R. E.
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p. 121 - 128
(2007/10/02)
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