- Copper(II) N, N, O-Chelating Complexes as Potential Anticancer Agents
-
Three novel dinuclear Cu(II) complexes based on a N,N,O-chelating salphen-like ligand scaffold and bearing varying aromatic substituents (-H, -Cl, and -Br) have been synthesized and characterized. The experimental and computational data obtained suggest that all three complexes exist in the dimeric form in the solid state and adopt the same conformation. The mass spectrometry and electron paramagnetic resonance results indicate that the dimeric structure coexists with the monomeric form in solution upon solvent (dimethyl sulfoxide and water) coordination. The three synthesized Cu(II) complexes exhibit high potentiality as ROS generators, with the Cu(II)/Cu(I) redox potential inside the biological redox window, and thus being able to biologically undergo Cu(II)/Cu(I) redox cycling. The formation of ROS is one of the most promising reported cell death mechanisms for metal complexes to offer an inherent selectivity to cancer cells. In vitro cytotoxic studies in two different cancer cell lines (HeLa and MCF7) and in a normal fibroblast cell line show promising selective cytotoxicity for cancer cells (IC50 about 25 μM in HeLa cells, which is in the range of cisplatin and improved with respect to carboplatin), hence placing this N,N,O-chelating salphen-like metallic core as a promising scaffold to be explored in the design of future tailor-made Cu(II) cytotoxic compounds.
- Pe?a, Quim,Sciortino, Giuseppe,Maréchal, Jean-Didier,Bertaina, Sylvain,Simaan, A. Jalila,Lorenzo, Julia,Capdevila, Mercè,Bayón, Pau,Iranzo, Olga,Palacios, òscar
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p. 2939 - 2952
(2021/03/08)
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- Proximity Histidine Labeling by Umpolung Strategy Using Singlet Oxygen
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While electrophilic reagents for histidine labeling have been developed, we report an umpolung strategy for histidine functionalization. A nucleophilic small molecule, 1-methyl-4-arylurazole, selectively labeled histidine under singlet oxygen (1O2) generation conditions. Rapid histidine labeling can be applied for instant protein labeling. Utilizing the short diffusion distance of 1O2 and a technique to localize the 1O2 generator, a photocatalyst in close proximity to the ligand-binding site, we demonstrated antibody Fc-selective labeling on magnetic beads functionalized with a ruthenium photocatalyst and Fc ligand, ApA. Three histidine residues located around the ApA binding site were identified as labeling sites by liquid chromatography-mass spectrometry analysis. This result suggests that 1O2-mediated histidine labeling can be applied to a proximity labeling reaction on the nanometer scale.
- Nakane, Keita,Sato, Shinichi,Niwa, Tatsuya,Tsushima, Michihiko,Tomoshige, Shusuke,Taguchi, Hideki,Ishikawa, Minoru,Nakamura, Hiroyuki
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supporting information
p. 7726 - 7731
(2021/05/29)
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- Copper nanoparticles (CuNPs) catalyzed chemoselective reduction of nitroarenes in aqueous medium
-
Abstract: A procedure for practical synthesis of CuNPs from CuSO4·5H2O is established, under appropriate reaction conditions, using rice (Oryza sativa) as an economic source of reducing as well as a stabilizing agent. Optical and microscopic techniques are employed for the characterization of the synthesized CuNPs and the sizes of the particles were found to be in the range of 8 ± 2 nm. The nanoparticles are used as a catalyst for chemoselective reduction of aromatic nitro compounds to corresponding amines under ambient conditions and water as a reaction medium. Graphic abstract: CuNPs are synthesized using hydrolysed rice and used as catalyst for chemoselective reduction of nitroarenes to their corresponding amines in water. [Figure not available: see fulltext.]
- Chand, Dillip Kumar,Rai, Randhir
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- C-H Amination of Arenes with Hydroxylamine
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This Letter describes the development of a TiIII-mediated reaction for the C-H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (30 min), compatibility with ambient moisture and air, scalability, and the use of inexpensive commercial reagents.
- See, Yi Yang,Sanford, Melanie S.
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p. 2931 - 2934
(2020/04/09)
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- Method for reducing aromatic nitro into arylamine
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The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.
- -
-
Paragraph 0137-0140
(2020/07/15)
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- Azobenzene-diamides as Photopharmacological Ligands for Insect Ryanodine Receptor
-
Photoresponsive ligands are powerful tool compounds for studying receptor function with spatiotemporal resolution. However, to the best of our knowledge, such a ligand is not available for the ryanodine receptor (RyR). Herein, we present a photochromic ligand (PCL) for insect RyR by decorating chlorantraniliprole (CHL) with photoswitchable azobenzene (AB). We demonstrated that one potent ligand, named ABCHL13, shows light-induced reversible trans-cis isomerization and 3.5-fold insecticidal activity decrease toward oriental armyworm (Mythimna separata) after UV-light irradiation, that is, trans-ABCH13 has higher activity than the cis-ABCH13. ABCHL13 enables optical control over intracellular Ca2+ release in dorsal unpaired median (DUM) neurons of M. separata and American cockroach (Periplaneta americana) and cardiac function of P. americana. Our results provide a first photopharmacological toolkit that is applicable to light-dependent regulation of RyR and heart beating.
- Chen, Meijun,Li, Yuxin,Shao, Xusheng,Wang, Long,Xia, Shanshan,Xu, Zhiping
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p. 14409 - 14416
(2020/12/22)
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- Method for preparing O-phenylenediamine from aniline
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The invention provides a method for preparing o-phenylenediamine from aniline. The method comprises the following steps: protecting an amino group on aniline by using an acetyl group, then mixing withan amino donor, an oxidant and a catalyst Pd-Cu/TS-1 to carry out an ammoniation reaction, carrying out deprotection, and separating to obtain o-phenylenediamine. A protecting group strategy is used,the acetyl group is adopted to protect the amino group on aniline, the catalyst is coordinated with a carbonyl group in acetanilide to induce and activate the o-position C-H bond, so the o-position selectivity is improved, the generation of byproducts is reduced, the ammoniation efficiency and selectivity can be greatly improved, and the yield and purity of o-phenylenediamine are improved; and the o-phenylenediamine is directly prepared from aniline, so the environmental pollution caused by nitrification and chlorination processes is avoided, and the method is more in line with the green andenvironment-friendly synthesis concept.
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-
- Metal-free Reduction of Nitro Aromatics to Amines with B 2 (OH) 4 /H 2 O
-
A metal-free reduction of nitro aromatics mediated by diboronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.
- Chen, Danyi,Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Liu, Qixing,Zhang, Kaili,Uozumi, Yasuhiro
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supporting information
p. 1765 - 1768
(2018/06/26)
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- Regioselective nitration of anilines with Fe(NO3)3·9H2O as a promoter and a nitro source
-
An efficient Fe(NO3)3·9H2O promoted ortho-nitration reaction of aniline derivatives has been developed. This reaction may go through a nitrogen dioxide radical (NO2) intermediate, which is generated by the thermal decomposition of iron(iii) nitrate. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the broad substrate scope and applications.
- Gao, Yang,Mao, Yuanyou,Zhang, Biwei,Zhan, Yingying,Huo, Yanping
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p. 3881 - 3884
(2018/06/08)
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- Cu-catalyzed reduction of azaarenes and nitroaromatics with diboronic acid as reductant
-
A ligand-free copper-catalyzed reduction of azaarenes with diboronic acid as reductant in an aprotic solvent under mild conditions has been developed. Most interestingly, the nitroazaarenes could be reduced exclusively to give the corresponding amines without touching the azaarene moieties. Furthermore, the reductive amination of aromatic nitro compounds and aromatic aldehydes has also been realized. A series of hydrogenated azaarenes and secondary amines were obtained with good functional group tolerance.
- Pi, Danwei,Zhou, Haifeng,Zhou, Yanmei,Liu, Qixing,He, Renke,Shen, Guanshuo,Uozumi, Yasuhiro
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p. 2121 - 2129
(2018/03/23)
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- Preparation method of o-phenylenediamine
-
The invention relates to a preparation method of o-phenylenediamine. A 2-aminoazo aromatic compound is used for reduction preparation, and reduction reaction is carried to obtain the o-phenylenediamine by one of the two following modes: the first mode com
- -
-
Paragraph 0004; 0008
(2019/01/14)
-
- Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid
-
An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.
- Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Pi, Danwei,Shen, Guanshuo
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p. 3898 - 3904
(2017/06/13)
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- Fe-Catalyzed Amination of (Hetero)Arenes with a Redox-Active Aminating Reagent under Mild Conditions
-
A novel and efficient Fe-catalyzed direct C?H amination (NH2) of arenes is reported using a new redox-active aminating reagent. The reaction is simple, and can be performed under air, mild, and redox-neutral conditions. This protocol has a broad substrate scope and could be used in the late-stage modification of bioactive compounds. Mechanistic studies demonstrate that a radical pathway could be involved in this transformation.
- Liu, Jianzhong,Wu, Kai,Shen, Tao,Liang, Yujie,Zou, Miancheng,Zhu, Yuchao,Li, Xinwei,Li, Xinyao,Jiao, Ning
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supporting information
p. 563 - 567
(2017/01/18)
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- Chitosan supported Zn(II) mixed ligand complexes as heterogeneous catalysts for one-pot synthesis of amides from ketones via Beckmann rearrangement
-
Chitosan supported Zn(II) mixed ligand complexes have been synthesized and characterized by FT-IR, UV–Vis, TGA, XRD, FESEM, EDX, AAS and Elemental Analysis. These complexes have been found to be efficient and recyclable heterogeneous catalysts for the one-pot synthesis of amides via Beckmann rearrangement. All three complexes can be easily filtered out from the reaction medium and reused up to five times without significant loss of catalytic activity. The reported protocol is economical and novel in the sense that amides can be easily synthesized in only one-step. All products were obtained as white to off-white crystalline solids and fully characterized by 1H NMR, FT-IR and Mass Spectra.
- Anuradha,Kumari, Shweta,Layek, Samaresh,Pathak, Devendra D.
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p. 368 - 373
(2016/11/03)
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- Folding Patterns in a Family of Oligoamide Foldamers
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A series of small, unsymmetrical pyridine-2,6-dicarboxylamide oligoamide foldamers with varying lengths and substituents at the end groups were synthetized to study their conformational properties and folding patterns. The @-type folding pattern resembled the oxyanion-hole motifs of enzymes, but several alternative folding patterns could also be characterized. Computational studies revealed several alternative conformers of nearly equal stability. These folding patterns differed from each other in their intramolecular hydrogen-bonding patterns and aryl-aryl interactions. In the solid state, the foldamers adopted either the globular @-type fold or the more extended S-type conformers, which were very similar to those foldamers obtained computationally. In some cases, the same foldamer molecule could even crystallize into two different folding patterns, thus confirming that the different folding patterns are very close in energy in spite of their completely different shapes. Finally, the best match for the observed NOE interactions in the liquid state was a conformation that matched the computationally characterized helix-type fold. Erase and refold: Like peptides, oligoamide foldamers fold into a number of different conformers that are very close in energy (see picture, stability energies in kcal mol-1 given in parentheses). By using a combination of computational, single-crystal X-ray diffraction, and NMR spectroscopic studies, these folding patterns have been identified and characterized for a family of seven different foldamers with varying substituents.
- Kortelainen, Minna,Suhonen, Aku,Hamza, Andrea,Pápai, Imre,Nauha, Elisa,Yliniemel?-Sipari, Sanna,Nissinen, Maija,Pihko, Petri M.
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supporting information
p. 9493 - 9504
(2015/06/30)
-
- Synthesis of 2-methyl-1-[(5-methylfuran-2-yl)methyl]- and 2-methyl-1-[(5-methylpyrrol-2-yl)methyl]-1H-benzimidazoles
-
A method for the synthesis of 2-methyl-1-[(5-methylfuran-2-yl)methyl]-1H- benzimidazoles based on the intramolecular cyclization of vicinal N-[(5-methylfuran-2-yl)methyl]aminoanilides has been developed. A study was carried out on the protolytic opening o
- Stroganova,Red'Kin,Kovalenko,Vasilin,Krapivin
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p. 1264 - 1273
(2014/01/17)
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- 2,4-DIAMINO-6,7-DIHYDRO-5H-PYRROLO[2,3]PYRIMIDINE DERIVATIVES AS FAK/Pyk2 INHIBITORS
-
The invention relates to a novel class of 2,4-diamino-6,7-dihydro-5H-pyrrolo[2,3]pyrimidine derivatives as a FAK and/or Pyk2 inhibitor, to a process for their preparation, and to a composition thereof, as well as to use of the compounds for the inhibiting FAK and/or Pyk2 and method for the treatment of a FAK and/ or Pyk2 mediated disorder or disease.
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Page/Page column 67
(2012/07/27)
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- Synthesis and photochemical properties of oligo-ortho-azobenzenes
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Azobenzenes have attracted great interest in recent years because of their ability to change conformation upon irradiation. This property has been featured in several applications not only in organic chemistry but also in biology. Even though monoazobenzenes have been extensively studied and documented in the literature, only a few methods are available for the synthesis of oligo-ortho-azobenzenes. Also, their photochemical properties have not been reported so far. This study shows an efficient strategy for the preparation of oligo-ortho-azobenzenes and the investigation of their photochemical properties. It is demonstrated that the absorption spectra are highly influenced by the substituents. Interestingly, none of the ortho-bis-, tris-, or tetra-azobenzenes showed any E → Z isomerization. Only the ortho-nitrogen-substituted monoazobenzenes' photochromic behavior upon UV irradiation was observed.
- Bellotto, Silvia,Reuter, Raphael,Heinis, Christian,Wegner, Hermann A.
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experimental part
p. 9826 - 9834
(2012/01/06)
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- Copper-catalyzed direct amination of ortho-functionalized haloarenes with sodium azide as the amino source
-
A simple copper-catalyzed direct amination of ortho-functionalized haloarenes (2-halobenzoic acid, 2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) has been developed with use of NaN3 as the amino source in ethanol, and the corresponding ortho-functionalized aromatic amines were synthesized in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN3 to lead to ortho-functionalized azidoarenes, followed by reduction with ethanol.
- Zhao, Haibo,Fu, Hua,Qiao, Renzhong
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experimental part
p. 3311 - 3316
(2010/08/05)
-
- CDK INHIBITORS
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The present invention relates to CDK inhibitors and their use in the treatment of cell proliferative diseases such as cancer.
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Page/Page column 61
(2010/07/09)
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- Synthesis and fungicidal activity of novel aminophenazine-1-carboxylate derivatives
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A series of novel 6-aminophenazine-1-, 7-aminophenazine-1- and 8-aminophenazine-1-carboxylate derivatives were synthesized by a facile method, and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry. Some unexpected byproducts V-7b-V-8d were noticed and isolated, and their structures were identified by 2D NMR spectra including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (Hmbc) and H-H correlation spectrometry (H-H COSY) approach. Their fungicidal activities against five fungi were evaluated, which indicated that most of the title compounds showed low fungicidal activities in vitro against Alternaria solanl, Cercospora arachidicola, Fusarium omysporum, Gibherella zeae, and Physalospora piricola at a dosage of 50 μg mL -1, while compounds IV-6a and IV-6b exhibited excellent activities against P. piricola at that dosage. Compound IV-6a could be considered as a leading structure for further design of fungicides. 2010 American Chemical Society.
- Wang, Ming-Zhong,Xu, Han,Yu, Shu-Jing,Feng, Qi,Wang, Su-Hua,Li, Zheng-Ming
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experimental part
p. 3651 - 3660
(2011/07/29)
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- Synthesis, photophysical and NMR evaluations of thiourea-based anion receptors possessing an acetamide moiety
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The synthesis and photophysical evaluation of three diaryl thiourea-based anion receptors (4-6) for comparison with their urea counterparts (1-3) is outlined. These anion receptors posses an acetamide functionality on one of the aryl groups and an electron-withdrawing CF3 group on the other. By varying the position of the acetamide group, in the o-, m- and p-positions of 4-6, respectively, the anion binding ability was both tuneable and found to be, in some cases, significantly different from that seen for the urea analogues 1-3. The binding affinities of the receptors 4-6, as well as the binding stoichiometries, were evaluated using UV-vis absorption spectroscopy in MeCN. However, these receptors were not sufficiently emissive to quantify the anion recognition using fluorescence. The results confirmed strong binding of these receptors to anions such as fluoride, acetate, phosphate, pyrophosphate and chloride. Nevertheless, the overall results obtained did not conform to the anticipated trends seen for 1-3, which is most likely due to the enhanced binding affinity of the thiourea analogues 4-6. The binding interactions were also investigated by using 1H NMR which confirmed that these receptors interacted with the anions in a stepwise manner, where the primary anion binding interaction occurred at the thiourea side, which led to an activation of the acetamide moiety towards the second anion binding interaction, an example of an allosteric activation mode.
- Boyle, Elaine M.,McCabe, Thomas,Gunnlaugsson, Thorfinnur
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experimental part
p. 586 - 597
(2011/01/03)
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- Highly enantioselective aldol reactions using N-arylprolinamides with enhanced acidity and double H-bonding potential
-
We have designed and synthesized N-arylprolinamides 7-10 with a potential to involve in the binding of electrophilic aldehydes via two N-H?O hydrogen bonds for application in organocatalytic aldol reactions. The catalyst 10 is shown to afford aldol produc
- Saha, Satyajit,Moorthy, Jarugu Narasimha
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supporting information; experimental part
p. 912 - 916
(2010/05/03)
-
- Regioselective syntheses of 2- and 4-formylpyrido[2,1-b]benzoxazoles
-
o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpy-rido[2,l-6]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2′-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,l-6]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for the formation of 5 involving sequential chlorination, dimerization, intramolecular elimination of HC1 to form the oxazole ring, formylation twice, and regioselective intramolecular nucleophilic cyclization to construct the pyridone ring is proposed.
- Li, Ke-Lai,Du, Zong-Bo,Guo, Can-Cheng,Chen, Qing-Yun
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supporting information; experimental part
p. 3286 - 3292
(2009/09/08)
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- Cross-coupling of aryl/heteroaryl bromides with ammonia using a copper-carbene catalyst
-
A variety of aryl and heteroaryl bromides were cross-coupled with ammonia in good to high yields in the presence of a copper-NHC catalyst. The Royal Society of Chemistry.
- Ntaganda, Rukundo,Dhudshia, Bhartesh,Macdonald, Charles L. B.,Thadani, Avinash N.
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supporting information; experimental part
p. 6200 - 6202
(2009/05/06)
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- The recognition and sensing of anions through "positive allosteric effects" using simple urea-amide receptors
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(Chemical Equation Presented) The design, synthesis, and X-ray crystallographic analysis of three simple diaryl-urea based anion receptors possessing an amide moiety on one of the aryl groups, and an electron withdrawing CF3 group on the other, is described. The three receptors differ only in the position of the amide functionality relative to the hydrogen bonding urea moiety (being para, meta, and ortho for 1, 2, and 3, respectively). This simple modification was shown to have a significant effect on the anion recognition ability, the strength of the recognition process, and the stoichiometry (host/guest) for these sensors. We demonstrate, by using both UV-vis absorption and 1H NMR spectroscopy, that these factors are caused by the ability of the amide moiety to both modulate the anion binding selectivity and the sensitivity of the urea moiety. We also demonstrate that, in the case of 1 and 2, this anion recognition at the urea moiety leads to concomitant activation (through enhanced inductive effect) in the amide functionality toward anions, which leads to the formation of an overall 1:2 (sensor/anion) binding stoichiometry for these receptors. This "activation" we describe as being an example of a "positive allosteric activation" by the urea site, caused directly by the first anion binding interaction, which to the best of our knowledge, has not been previously demonstrated for anion recognition and sensing.
- Dos Santos, Cidalia M. G.,McCabe, Thomas,Watson, Graeme W.,Kruger, Paul E.,Gunnlaugsson, Thorfinnur
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supporting information; experimental part
p. 9235 - 9244
(2009/04/06)
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- Selective reduction of aromatic nitro groups in the presence of amide functionality
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Pressure mediated selective reduction of aromatic nitro groups in the presence of amide functionality has been achieved by use of hydrazine hydrate.
- Deka, Dibakar Chandra,Kakati, Hari Sankar
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p. 223 - 224
(2007/10/03)
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- Eco-friendly reductive acetamidation of arylnitro compounds by thioacetate anion through in situ catalytic regeneration: application in the synthesis of Acetaminophen
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A novel one-step reductive acetamidation of arylnitro compounds mediated by thioacetate anion in thioacetic acid via in situ catalytic regeneration was developed and applied to an efficient synthesis of Acetaminophen.
- Bhattacharya, Apurba,Suarez, Victor,Tamez Jr., Victoriano,Wu, Jiejun
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p. 3221 - 3223
(2007/10/03)
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- Zeolites. Efficient and eco-friendly catalysts for the synthesis of benzimidazoles
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A superior method of synthesis of 2-substituted benzimidazoles by means of the heterogeneous catalysis of synthetic and natural zeolites in the reaction of 1,2-diaminobenzene with acid chlorides is described. Springer-Verlag 2005.
- Heravi, Majid M.,Tajbakhsh, Mahmood,Ahmadi, Amir N.,Mohajerani, Bagher
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p. 175 - 179
(2007/10/03)
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- Chemoselective acylation of amines in aqueous media
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Amines are efficiently acylated by both cyclic and acyclic anhydrides by dissolving them in an aqueous medium with the help of a surfactant, sodium dodecyl sulfate (SDS). Cyclic and acyclic anhydrides react with equal ease with an amine, and amines with various stereo-electronic factors react at the same rates with an anhydride. Chemoselective acylation of amines in the presence of phenols and thiols and of thiols in the presence of phenols has been achieved. No acidic or basic reagents are used during the reaction. No Chromatographic separation is required for isolation of the acylated products. Reactions in a neutral aqueous medium, easy isolation of products, and innocuous by-products make the present method a green chemical process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Naik, Sarala,Bhattacharjya, Gitalee,Talukdar, Bandana,Patel, Bhisma K.
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p. 1254 - 1260
(2007/10/03)
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- BF3·Et2O promoted one-pot expeditious and convenient synthesis of 2-substituted benzimidazoles and 3,1,5-benzoxadiazepines
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2-Substituted benzimidazoles and 3,1,5-benzoxadiazepines have been synthesized in excellent yields in a single pot by cyclodehydration of N-acyl-1,2-phenylenediamines and N,N′-diacyl-1,2- phenylenediamines prepared in situ from the corresponding 1,2-phenylenediamines and an acid chloride, respectively.
- Tandon, Vishnu K.,Kumar, Manoj
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p. 4185 - 4187
(2007/10/03)
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- Inhibitors of human phosphatidylinositol 3-kinase delta
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Methods of inhibiting phosphatidylinositol 3-kinase delta isoform (PI3Kδ) activity, and methods of treating diseases, such as disorders of immunity and inflammation, in which PI3Kδ plays a role in leukocyte function are disclosed. Preferably, the methods employ active agents that selectively inhibit PI3Kδ, while not significantly inhibiting activity of other PI3K isoforms. Compounds are provided that inhibit PI3Kδ activity, including compounds that selectively inhibit PI3Kδ activity. Methods of using PI3Kδ inhibitory compounds to inhibit cancer cell growth or proliferation are also provided. Accordingly, the invention provides methods of using PI3Kδ inhibitory compounds to inhibit PI3Kδ-mediated processes in vitro and in vivo.
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Page column 98
(2008/06/13)
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- Nitroarene reduction using Raney nickel alloy with ammonium chloride in water
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Aromatic nitroarenes are reduced in high yields using a user-friendly combination of Raney nickel alloy and ammonium chloride in water at 80-90°C.
- Bhaumik, Kankan,Akamanchi
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p. 197 - 198
(2007/10/03)
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- An easy method for the generation of amides from ketones by a Beckmann type rearrangement mediated by microwave
-
A facile and efficient procedure is developed for one-pot synthesis of amides from ketones in the presence of P2O5/SiO 2 reagent in dry media under microwave irradiation. Ketoximes indirectly in the same conditions gave amides by Beckmann rearrangement.
- Eshghi, Hossein,Gordi, Zinat
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p. 2971 - 2978
(2007/10/03)
-
- C2-Symmetric ligands containing hydrogen bond donors: Synthesis and properties of Cu(II) complexes of 2,6-bis[N,N′-(2-carboxamidophenyl)carbamoyl]pyridine
-
The synthesis of the new tridentate ligands 2,6-bis[N,N′-(2-acetamidophenyl)carbamoyl]pyridine (H41Me) and 2,6-bis[N,N′-(2-ferrocenylamidophenyl)carbamoyl]pyridine (H41Fc), and their corresponding CuII/sup
- Shirin, Zahida,Thompson, Joel,Liable-Sands, Louise,Yap, Glenn P. A.,Rheingold, Arnold L.,Borovik
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p. 1714 - 1720
(2007/10/03)
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- Hydrogenation of ortho-substituted nitrobenzenes over palladium catalysts
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Hydrogenation of o-nitrobenzenes, under mild conditions (1 atm of hydrogen, 20-40°C, organic solvents) over a Pd/C catalyst and the palladium-containing anion exchangers AN-1 and AV-17-8 proceeds without the formation of intermediate products. The yield of primary amines varies from 25 to 100%. It was shown that the palladium-containing anion exchangers are superior to Pd/C in selectivity and stability in the hydrogenation of o-nitrobenzenes. Based on quantum-chemical calculations of substrate molecules, a two-parameter correlation was proposed to describe the electronic and steric effects of the substituent on the hydrogenation rate.
- Klyuev,Volkova,Abdullaev
-
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- A short synthesis of phenanthro[2,3-d]imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles
-
Methyl cis-deisopropyldehydroabietate was selectively nitrated at the 12-position by reaction with 'claycop', a montmorillonite clay impregnated with copper(II) nitrate. The 12-nitro compound was reduced to the corresponding amine and this was subjected to a combined acylation and ortho nitration. The compounds so produced were further converted into octahydro-1H-phenanthro[2,3-d]imidazoles by reductive cyclization. The same acylation-ortho nitration methodology was shown to provide a short synthesis of 2-substituted benzimidazoles from aniline.
- Fonseca, Tatiana,Gigante, Bárbara,Gilchrist, Thomas L
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p. 1793 - 1799
(2007/10/03)
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- Formic acid with 10% palladium on carbon: A reagent for selective reduction of aromatic nitro compounds
-
The nitro group in aromatic nitro compounds also containing reducible substituents such as carbonyl, ethene, ethyne, nitrile, acid, phenol etc, is selectively and rapidly reduced at room temperature to corresponding amino derivatives in good yield employing formic acid in the presence of 10% palladium on carbon. The catalyst could be recovered and reused after washing with water and ethanol, and the results obtained indicate further, there is no apparent loss of catalytic activity.
- Channe Gowda,Gowda
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p. 709 - 711
(2007/10/03)
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- Synthesis of acetylenic and diacetylenic diamines by alkynylation of o-phenylenediamine
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Reactions of o-phenylenediamine with 2-propynyl bromide and 1-bromo-2,4-undecadiyne in a nonpolar solvent lead to formation of the corresponding N-monoalkynylated products. Increase in the solvent polarity favors alkynylation at the second amino group to
- Balova,Remizova,Pashchenko
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p. 1476 - 1479
(2007/10/03)
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- Synthesis and structural study of phospholidines derived from aromatic amides
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The preparation and structural study in solution by 1H, 13C and 31P NMR spectroscopy of 2-dimethylamine-N-acetylbenzoxazaphospholidine 1b, 2-dimethylamine-N-acetylbenzo diazaphospholidine 2b, 2-dimethyl-N,N'-diacetylbenzoxazaphospholidine 3b, bis-1,2-ethane 4b, bis oxalyl 5b.The reaction of compounds 1b-5b with BH3DMS afforded the corresponding P-BH3 adducts without reducing the heterocycles, 1c-5c were also studied by 11B NMR.The solid state structure determined by X-ray diffraction analysis of 1b and 3b shows phosphorus atoms with 45percent of sp3 character and with the NMe2 group in axial position. - Keywords: aromatic phospholidines; amides heterocycles; phosphorus-borane adducts; NMR; X-ray diffraction.
- Matrinez-Martinez, Francisco Javier,Leon-Romo, Jose Luis,Padilla-Martinez, Itzia I.,Rosales-Hoz, Maria de Jesus,Contreras, Rosalinda
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p. 217 - 226
(2007/10/03)
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- Chemoselectivity of 6-Bromo-2-methyl-3,1-benzoxazin-4-one towards Amines, Schiff Bases, and Azines
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6-Bromo-2-methyl-3,1-benzoxazin-4-one (1) undergoes an unusual cleavage at position 4 when it is allowed to react with o-phenylenediamine or anthranilic acid in dry benzene to give the corresponding compounds 2 5, respectively. The reaction of 1 with Schiff bases and azines results in the formation of the compounds 6a d and 8a, b, respectively. The reaction involves a cleavage of the Schiff base or the azine into its amine and arylidene moieties which are smoothly incorporated into 1 via nucleophilic attack of the amine at position 4 and condensation of the aldehyde with a reactive methyl group, at position 2 respectively. No displacement of the arylidene segment was observed.
- Derbala
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p. 103 - 110
(2007/10/03)
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- Chemical and Electrochemical Reduction of ortho-Nitroanilides. A Combined Chemical, Polarographic and EPR Study
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The acetyl and benzoyl o-nitroanilines 1a and 1b and the acetyl and benzoyl o-nitrodiphenylamines 1c and 1d have been reduced chemically (t-BuOK/DMSO) and electrochemically inside the cavity of an EPR spectrometer.For all compounds the EPR signal of the radical anions could be recorded and interpreted.In DMSO the radical anions 1c(1-) and 1d(1-) evolved to the phenazine radical anion within 1 h.The polarographic study showed that the four compounds are reduced in two different steps, the first being monoelectronic and reversible, as demonstrated by cyclic voltammetric experiments.Compounds 1a-d were reduced with Fe/AcOH to the benzimidazoles 5a-d.The catalytic reduction of 1a gave the hydroxy-2-methylbenzimidazole 7a together with the azoxy derivative 6a.The macroscale electrolysis of 1c and 1d may be regarded as a convenient synthetic method of preparing benzimidazoles 5c and 5d, while the catalytic reduction may be considered the best route to benzimidazole N-oxides 4c and 4d.
- Alberti, Angelo,Carloni, Patricia,Greci, Lucedio,Stipa, Pierluigi,Andruzzi, Romano,et al.
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p. 1019 - 1023
(2007/10/02)
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- Reduction of Aromatic Nitro Compounds with Baker's Yeast
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The reduction of the nitro group of aromatic nitro compounds with baker's yeast was strongly influenced by the nature of the substituent on nitrobenzene, and in the reaction of acyl nitrobenzenes, selective reduction occurred to give optically active nitro alcohol and amino alcohol and amino ketone without giving any amino alcohol.Keywords baker's yeast; nitro compound; selective reduction; acyl nitrobenzene; chiral nitro alcohol
- Takeshita, Mitsuhiro,Yoshida, Sachiko,Kiya, Rieko,Higuchi, Naoko,Kobayashi, Yumi
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p. 615 - 617
(2007/10/02)
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- 2-Substituted phenyl-4,5,6,7-tetrahydro-2H-iso-indole-1,3-diones, and their production and use
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A 2-substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione of the formula: STR1 wherein X is a chlorine atom or a bromine atom and R is a C1 -C6 alkyl group, a C3 -C7 cycloalkyl group, a C3 -Cs
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- 2-substituted phenyl-4,5,6,7,-tetrahydro-2H-indole-1,3,-diones, and their production and use
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3-Amino-4-fluoro-6-halophenylthioacetic acids of the formula: STR1 and 5-substituted acetanilides of the formula: STR2 , which are intermediary compounds for the synthesis of herbicidally effective 2-substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-
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- o-Nitrobenzylidene Compounds. Part 4. The Cyanide-induced Cyclisation of o-Acetamido-N-(o-nitrobenzylidene)anilines: an Improved Route to Quinoxalinocinnolines
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Cyclisation of o-acetamido-N-(o-nitrobenzylidene)anilines (7) with potassium cyanide in methanol (preferably under nitrogen) leads in most cases to quinoxalinocinnolines (6) of unambiguous substitution pattern.In some cases, cyclisation appears to be incomplete, and 2-amino-3-(o-nitrophenyl)quinoxalines (11) are obtained as by-products; in certain cases quinoxalinocinnoline 5-oxides (10) are also detected.These by-products are assumed to result from oxidation of intermediates in the cyclisation process (7) ----> (6).
- Shepherd, Thomas,Smith, David M.
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p. 501 - 506
(2007/10/02)
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- Development of a Solar Energy Storage Process. Photoisomerization of a Norbornadiene Derivative to a Quadricyclane Derivative in an Aqueous Alkaline Solution
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In an aqueous alkaline solution, the photoisomerization of norbornadiene derivatives 1 to quadricyclane derivatives 2 was investigated.Upon irradiation with sunlight, 1a-g isomerized quantitatively to 2a-g even in the presence of air, although the reactio
- Maruyama, Kazuhiro,Tamiaki, Hitoshi,Kawabata, Shigeki
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p. 4742 - 4749
(2007/10/02)
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- Investigations of the Kinetics and Mechanism of Polarographic Reduction of o-, m- and p-Nitroacetanilides in Aqueous Ethanolic Medium
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Polarographic behaviour of o-, m- and p-nitroacetanilides in aqueous ethanolic solutions has been studied as a function of pH using NaNO3 (0.1 M) and Triton X-100 (0.001 percent) as the supporting electrolyte and maxima suppressor, respectively with a view to investigate the kinetics and mechanism of the reduction of o-, m- and p-nitroacetanilides at d.m.e.The reduction of the depolarizers has been found diffusion-controlled and irreversible.The potential-dependent rate constant, kf,h, has been calculated by Koutecky's method at different pH and the values of kinetic parameters (αna and k0f,h) have been calculated from log kf,h vs Ed,e plots which are linear thereby indicating that only a single rate-determining step is involved in the electrode process of each depolarizer.Based on the values of αna and the variation of E1/2 with pH, the stoichiometry of the rate-determining step involved in the reduction of each depolarizer at d.m.e. has been established.A tentative mechanism for the polarographic reduction of each depolarizer has been postulated.
- Singh, Mukhtar
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p. 737 - 740
(2007/10/02)
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- Piperazinylcarbostyril compounds
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A piperazinylcarbostyril compound of the formula (I) STR1 wherein R1 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a phenyl-lower alkyl group; R2 represents a hydrogen atom or a lower alkoxy group; R3 represents a hydrogen atom, a lower alkanoyl group, a furoyl group, a pyridylcarbonyl group, a lower alkanesulfonyl group, a lower alkoxycarbonyl group, a lower alkoxycarbonyl-lower alkyl group, a phenylsulfonyl group which may be substituted with a lower alkyl group on the benzene ring thereof, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a phenylcarbonyl group, a phenyl-lower alkyl group or a phenyl-lower alkanoyl group where each of said phenylcarbonyl group, phenyl-lower alkyl group and phenyl-lower alkanoyl group may be substituted with 1 to 3 of a lower alkoxy group, a halogen atom, a lower alkyl group, a cyano group, a nitro group, an amino group, a hydroxy group, a lower alkanoylamino group, a lower alkylthio group and a lower alkanoyloxy group, or with a lower alkylenedioxy group on the benzene ring thereof; and the bonding between the 3- and 4-positions of the carbostyril nucleus is a single bond or a double bond; or its pharmaceutically acceptable salt, useful as a cardiotonic agent.
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