- Design, synthesis, anti-inflammatory activity, and molecular docking studies of perimidine derivatives containing triazole
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We report here the design, synthesis, and anti-inflammatory activities of a series of perimidine derivatives containing triazole (5a–s). The chemical structures of the synthesized compounds have been assigned on the basis of IR, 1H NMR, 13C NMR, and HRMS spectral analyses. The anti-inflammatory properties of the synthesized perimidine derivatives were evaluated in a lipopolysaccharide (LPS)-stimulated inflammation model. Among the tested compounds, compound 7-(3-methylbenzyl)-7H-[1,2,4]triazolo[4,3-a]perimidine (hereafter referred to as 5h) and compound 7-(2-fluorobenzyl)-7H-[1,2,4]triazolo[4,3-a]perimidine (hereafter referred to as 5n) caused a reduction in the levels of the pro-inflammatory cytokines—tumor necrosis factor (TNF)-α and interleukin (IL)-6—in RAW264.7 cells. The anti-inflammatory potential of compounds 5h and 5n was also evaluated in vivo in a xylene-induced ear inflammation model. Compound 5n showed the most potent anti-inflammatory activity with an inhibition of 49.26% at a dose of 50 mg/kg. This activity is more potent than that of the reference drug ibuprofen (28.13%), and slightly less than that of indometacin (49.36%). To further elucidate the mechanisms underlying these inhibitory effects, LPS-induced nuclear factor-κB (NF-κB) activation and mitogen-activated protein kinase (MAPK) phosphorylation were studied. The results of western blotting showed that the extract obtained from compound 5n inhibited NF-κB (p65) activation and MAPK (extracellular signal-regulated kinase (ERK) and p38) phosphorylation in a dose-dependent manner. Moreover, the results of a docking study of compound 5n into the COX-2 binding site revealed that its mechanism was possibly similar to that of naproxen, a COX-2 inhibitor. The effect of compound 5n on COX-2 antibody was showed it could significantly inhibit COX-2 activity.
- Zhang, Hong-Jian,Wang, Xiu-Zhi,Cao, Qi,Gong, Guo-Hua,Quan, Zhe-Shan
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Read Online
- A synthetic nucleoside probe that discerns a DNA adduct from unmodified DNA
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Selective pairing of engineering nucleosides in DNA duplexes provides a potential means to probe structurally modified DNA bases (i.e., DNA adducts) and address challenges associated with correlating adduct chemical structure with biological impact. The c
- Gong, Jiachang,Sturla, Shana J.
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Read Online
- Electrochemical access to benzimidazolone and quinazolinone derivatives: Via in situ generation of isocyanates
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Isocyanates are the key intermediates for several organic transformations towards the synthesis of diverse pharmaceutical targets. Herein, we report the development of an oxidant-free protocol for electrochemical in situ generation of isocyanates. This strategy highlights expedient access to benzimidazolones and quinazolinones and eliminates the need for exogenous oxidants. Furthermore, detailed mechanistic studies provide strong support towards our hypothesis of in situ isocyanate generation. This journal is
- Saha, Debarshi,Taily, Irshad Maajid,Naik, Sumitra,Banerjee, Prabal
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supporting information
p. 631 - 634
(2021/01/29)
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- Synthesis of Urea Derivatives from CO2 and Silylamines
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A series of thirty-three N,N′-diaryl, dialkyl, and alkyl-aryl ureas have been prepared in pyridine or toluene by reaction of silylamines with CO2. This protocol is shown to provide facile access to 13C-labeled ureas, as well as chiral and macrocyclic ureas. These reactions proceed through initial generation of the corresponding silylcarbamates, which subsequently react with silylamine under thermal conditions to afford the thermodynamically favored urea and disilyl ether.
- Xu, Maotong,Jupp, Andrew R.,Ong, Maegan S. E.,Burton, Katherine I.,Chitnis, Saurabh S.,Stephan, Douglas W.
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supporting information
p. 5707 - 5711
(2019/04/16)
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- Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
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Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
- Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
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supporting information
p. 10907 - 10912
(2019/08/02)
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- ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE ORGANOMETALLIC COMPOUND, AND ORGANIC LIGHT-EMITTING APPARATUS INCLUDING THE ORGANIC LIGHT-EMITTING DEVICE
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Provided are an organometallic compound, an organic light-emitting device including the organometallic compound, and an organic light-emitting apparatus including the organic light-emitting device. The organometallic compound has the structure M(L1)n1(L2)n2, wherein M is a transition metal, L1 is a ligand represented by the following structure: wherein n1 is 1, 2, or 3, and when n1 is two or more, two or more L1(s) are identical to or different from each other, L2 is an organic ligand, and n2 is 0, 1, or 2, and when n2 is two or more, two or more L2(s) are identical to or different from each other. The sum of n1 and n2 is 2 or 3. More details about Formula 2 is provided in the disclosure.
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Paragraph 0344; 0345
(2019/09/06)
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- Heterocyclic compounds and organic electroluminescence devices thereof
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The invention provides heterocyclic compounds and organic electroluminescence devices thereof, and belongs to the technical field of organic electroluminescence materials. Amine type groups are introduced to specific positions of a naphthalene ring, thus properly adjusting the hole mobility and achieving an objective of balancing the hole mobility and carrier mobility. An exciton composition zoneis completely in a luminescence layer. A triarylamine structure is connected to an amine group on one side of the heterocyclic compounds to increase hole transporting capability. In addition, a carbonatom is provided with two substitute groups, making structures of the compounds similar to the structure of spirofluorene, thus ensuring that the compounds have higher glass transition temperatures.A technical problem that organic electroluminescence materials in the prior art have poor luminescence properties such as low luminescence efficiency and short service lifetime is solved. Compared with the prior art, the organic electroluminescence devices based on organic electroluminescence materials and ink compositions have improved luminescence properties and the compounds are excellent OLEDmaterials.
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Paragraph 0062-0064
(2018/12/01)
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- A heterocyclic compound and its organic light-emitting device (by machine translation)
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The present invention provides a heterocyclic compound and its organic light-emitting device, which belongs to the technical field of organic photoelectric material. In particular in the specific position of the naphthalene ring is introduced on the amide group, thus can be appropriate adjusting hole mobility, reach the hole mobility and balance the purpose of carrier mobility. The exciton consistent with the regional totally in the luminescent layer. Heterocyclic compounds at one side of the amide group on the amine structure connected, increase its hole transmission ability. At the same time a relatively large molecule volume and molecular weight it ensures that this material has higher glass transition temperature. In the prior art can be effectively solve the organic photoelectric material luminous efficiency is low, the driving voltage is relatively high, and short service life of the technical problem of poor performance of the. Compared with the prior art, the invention is based on organic electroluminescent material and ink composition of the organic light-emitting device, can significantly improve the luminescence, is an excellent OLED material. (by machine translation)
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Paragraph 0055; 0056; 0057
(2019/01/05)
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- Stoichiometric Reactions of CO2 and Indium-Silylamides and Catalytic Synthesis of Ureas
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The indium compounds In(N(SiMe3)2)2Cl?THF (2) and In(N(SiMe3)2)Cl2?(THF)n (3) were shown to react with CO2 to give [(Me3Si)2N)InX(μ-OSiMe3)]2 (X=N(SiMe3)2 4, Cl 5). 0.05–2.0 mol % of the species 3 acts as a pre-catalyst for the conversion of aryl and alkyl silylamines under CO2 (2–3 atm) to give the corresponding ureas in 70–99 % yields. A proposed mechanism is supported by experimental and computational data.
- Xu, Maotong,Jupp, Andrew R.,Stephan, Douglas W.
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supporting information
p. 14277 - 14281
(2017/10/31)
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- TETRAAMINE DERIVATIVE, METHOD FOR PRODUCING THE SAME, AND ORGANIC ELECTRONIC DEVICE USING THE SAME
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PROBLEM TO BE SOLVED: To provide a tetraamine derivative having naphthalene or perylene as a skeleton with cyclic urea bonds, which can be used as a coating-type organic semiconductor material such as an organic thin film transistor (organic TFT), an organic electroluminescent element (organic EL element), and an organic thin film solar cell, and a method for synthesizing the same. SOLUTION: There is provided as a coating-type semiconductor material, for example, a tetraamine derivative having a naphthalene skeleton with cyclic urea bonds, which can be obtained according to the following reaction formula. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0073-0076
(2018/10/24)
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- Visible light photoredox catalysis: Aerobic oxidation of perimidines to perimidinones
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Aerobic oxidation of a series of 2,3-dihydro-1H-perimidines to the corresponding 4- and 6-perimidinones via visible light photoredox catalysis using Ru(bpy)32+ as a catalyst was reported. The scope and limitation of this oxidation were investigated and a possible photochemical mechanism was proposed.
- Wu, Chun-Ku,Liou, Teau-Jiuan,Wei, Hao-Yi,Tsai, Pei-Shan,Yang, Ding-Yah
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p. 8219 - 8225
(2015/03/05)
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- Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR
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Basic molecular building blocks such as benzene rings, amidines, guanidines, and amino groups have been combined in a systematic way to generate ligand candidates for HIV-1 TAR RNA. Ranking of the resulting compounds was achieved in a fluorimetric Tat-TAR
- Zeiger, Mirco,Stark, Sebastian,Kalden, Elisabeth,Ackermann, Bettina,Ferner, Jan,Scheffer, Ute,Shoja-Bazargani, Fatemeh,Erdel, Veysel,Schwalbe, Harald,G?bel, Michael W.
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supporting information
p. 5576 - 5580
(2015/01/08)
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- Scope of chemical fixation of carbon dioxide catalyzed by a bifunctional monomeric tungstate
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The tungsten-oxo moiety in a simple monomeric tungstate, TBA 2[WO4] (I, TBA = tetra-n-butylammonium), showed bifunctional activation of both CO2 and 1,2-phenylenediamine (1a). It was confirmed by 1H, 13C, and 183W NMR spectroscopies that adducts I-1a and I-(CO2)n (n = 1 and 2) were formed by the reactions of I with 1a and CO2, respectively. These adducts played important roles in formation of the corresponding carbamic acid intermediates. The present bifunctionality could be applied to chemical fixation of CO2 even at atmospheric pressure with various kinds of structurally diverse aryl diamines, primary monoamines, propargylic alcohols, and propargylic amines into cyclic urea derivatives, 1,3-disubstituted urea derivatives, cyclic carbonates, and cyclic carbamates, respectively.
- Kamata, Keigo,Kimura, Toshihiro,Sunaba, Hanako,Mizuno, Noritaka
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p. 160 - 166
(2014/03/21)
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- A bifunctional tungstate catalyst for chemical fixation of CO2 at atmospheric pressure
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No pressure: A simple monomeric tungstate, [WO4]2-, serves as a highly efficient homogeneous catalyst for various transformations of CO2 at atmospheric pressure. The tungsten-oxo moiety activates CO2 and the substrate simultaneously. The catalyst system is high yielding and applicable to a wide range of substrates such as amines (see scheme), 2-aminobenzonitriles, and propargylic alcohols. Copyright
- Kimura, Toshihiro,Kamata, Keigo,Mizuno, Noritaka
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supporting information; experimental part
p. 6700 - 6703
(2012/08/28)
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- NEW ORGANIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME
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Disclosed is a compound represented by formula 1: [formula 1] wherein each of A, X, Y, Y' and Y'' has the same meaning as described herein. When used in an organic light emitting device, the compound represented by formula 1 has at least one function selected from the group consisting of hole injection, hole transport, light emitting, electron transport, electron injection, etc., depending on the type of each unit forming the trimer or substituents in each unit. An organic light emitting device is also disclosed. The organic light emitting device includes a first electrode, an organic film having one or more layers and a second electrode, laminated successively, wherein at least one layer of the organic film includes at least one compound represented by formula 1.
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- Organic compound and organic light emitting device using the same
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Disclosed is a compound represented by formula 1: [formula 1] wherein each of A, X, Y, Y′ and Y″ has the same meaning as described herein. When used in an organic light emitting device, the compound represented by formula 1 has at least one function selected from the group consisting of hole injection, hole transport, light emitting, electron transport, electron injection, etc., depending on the type of each unit forming the trimer or substituents in each unit. An organic light emitting device is also disclosed. The organic light emitting device includes a first electrode, an organic film having one or more layers and a second electrode, laminated successively, wherein at least one layer of the organic film includes at least one compound represented by formula 1.
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- Efficient synthesis of ureas by direct palladium-catalyzed oxidative carbonylation of amines
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A general synthesis of symmetrically disubstituted ureas and trisubstituted ureas by direct Pd-catalyzed oxidative carbonylation of primary amines or of a mixture of a primary and a secondary amine, respectively, with unprecedented catalytic efficiencies for this kind of process, is reported. Reactions are carried out at 90-100 °C in DME as the solvent in the presence of PdI 2 in conjunction with an excess of KI as the catalytic system and under 20 atm of a 4:1 mixture of CO and air. In some cases, working in the presence of an excess of CO2 (40 atm) in addition to CO and air (60 atm total) had a beneficial effect on substrate reactivity and product yield. Cyclic five-membered and six-membered ureas were easily formed from primary diamines. The methodology has been successfully applied to the synthesis of pharmacologically active ureas, such as those deriving from α-amino esters or urea NPY5RA-972, a potent antagonist of the neuropeptide Y5 receptor.
- Gabriele, Bartolo,Salerno, Giuseppe,Mancuso, Raffaella,Costa, Mirco
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p. 4741 - 4750
(2007/10/03)
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- A NEW SYNTHESIS OF HETEROCYCLES VIA CARBONILATION OF AMINES WITH CARBON MONOXIDE IN THE PRESENCE OF SELENIUM
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Amines which contain a second functional group in the appropriate position react with carbon monoxide in the presence of selenium to form heterocyclic derivatives in which carbon monoxide is incorporated.For instance, diamines, aminoalcohols, and their related compounds undergo carbonylation to give cyclic ureas, urethanes and the corresponding carbonylated compounds.For diamines and amino alcohols with more than two carbon atoms between the functional groups, intermolecular carbonylative coupling takes place competing with the intramolecular reaction.High selectivity has been attained under specified reaction conditions.Anilines having cyano or acetyl groups on the ortho position afford new classes of selenium-containing heterocycles.In these reactions, carbamoselenoate has been suggested as the common key intermediate.
- Yoshida, Tohru,Kambe, Nobuaki,Ogawa, Akiya,Sonoda, Noboru
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p. 137 - 148
(2007/10/02)
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- Potential Antitumor Agents. 53. Synthesis, DNA Binding Properties, and Biological Activity of Perimidines Designed as "Minimal" DNA-Intercalating Agents
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A series of compounds based on perimidine have been synthesized and evaluated for their DNA-binding properties and antitumor activity.The fused tricyclic perimidine chromophore appears to be the minimal structural requirement for intercalative binding to DNA since the mode of binding could be dictated by the position of attachment of the side chain.The intercalating compounds have DNA association constants (log K = 5.8-6.5) and cytotoxic potencies (IC50 = 500-1500 nM) comparable to those shown by other classes of linear, tricyclic DNA-intercalating antitumor agents (acridinecarboxamides, phenazinecarboxamides), but none of the compounds showed in vivo activity.
- Herbert, John M.,Woodgate, Paul D.,Denny, William A.
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p. 2081 - 2086
(2007/10/02)
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- A New Synthesis of Cyclic Ureas, Cyclic Urethanes, and a Quinazolinedione. Selenium-Assisted Carbonylation of Aromatic Amines with Carbon Monoxide
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Five-, six-, and seven-membered cyclic ureas were synthesized in excellent yields from various aromatic diamines by reaction with carbon monoxide and a stoichiometric or excess amount of selenium in the presence of an oxidizing agent such as oxygen or dimethyl sulfoxide producing selectively the five- and six-membered cyclic ureas.In the case of 2-(2-aminoethyl)aniline under the catalytic conditions, intra- and intermolecular carbonylation competed resulting in the formation of a mixture of the seven-membered cyclic urea, 1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one and the acyclic urea, 1,3-bisurea.The distribution ratio of these two products varied depending on the reaction conditions, but selective formation of the cyclic urea was attained only when a stoichiometric or excess amount of selenium was used.In addition to the above diamino compounds, 2-carbamoylaniline, 2-amino-3-pyridinol, and 2-(hydroxymethyl)-aniline also underwent similar carbonylation to give 2,4(1H,3H)-quinazolinedione, oxazolopyridin-2-(3H)-one, and 1,4-dihydro-2H-3,1-benzoxazin-2-one, respectively.
- Yoshida, Tohru,Kambe, Nobuaki,Murai, Shinji,Sonoda, Noboru
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p. 1793 - 1800
(2007/10/02)
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- BEHAVIOUR OF SOME PERIMIDINES TOWARDS OXIDANTS
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The oxidation of some perimidines with 3-chloroperbenzoic acid, trifluoroperacetic acid, and dipotassium nitrosodisulphonate is reported.Perimidine-2-thione is oxidised to perimidine-2-sulphonic acid, while other perimidines are oxidised to give 4- and 6-perimidinones.
- Herbert, John M.,Woodgate, Paul D.,Denny, William A
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p. 1043 - 1050
(2007/10/02)
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