- Iron-catalyzed cross-coupling of N?methoxy amides and arylboronic acids for the synthesis of N-aryl amides
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An efficient iron-catalyzed synthesis of N-aryl amides from N?methoxy amides and arylboronic acids is developed. FeCl3 is used as the sole catalyst for the cross-coupling reaction between N?methoxy amides and arylboronic acids without any other
- Li, Jinhui,Liu, Jin-Biao,Luo, Nianhua,Qiu, Guanyinsheng,Ren, Shangfeng,Wang, Ying,Xie, Huilin
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- Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP)
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This work describes the application of pentafluoropyridine (PFP), a cheap commercially available reagent, in the deoxyfluorination of carboxylic acids to acyl fluorides. The acyl fluorides can be formed from a range of acids under mild conditions. We also demonstrate that PFP can be utilized in a one-pot amide bond formation via in situ generation of acyl fluorides. This one-pot deoxyfluorination amide bond-forming reaction gives ready access to amides in yields of ≤94%.
- Brittain, William D. G.,Cobb, Steven L.
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supporting information
p. 5793 - 5798
(2021/08/01)
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- Manganese Catalyzed Direct Amidation of Esters with Amines
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The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.
- Fu, Zhengqiang,Wang, Xinghua,Tao, Sheng,Bu, Qingqing,Wei, Donghui,Liu, Ning
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p. 2339 - 2358
(2021/02/03)
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- Synthesis of polyaramids in γ-valerolactone-based organic electrolyte solutions
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The current synthetic procedures for polyaramids mainly involve the use of amide solvents such asN-methylpyrrolidone andN,N-dimethylacetamide. However, these solvents are suspected to be teratogenic and are considered ‘Substances of Very High Concern’ by the European Commission. Here we propose a benign alternative solvent system: an Organic Electrolyte Solution (OES) consisting of γ-valerolactone (GVL) and a small amount of the ionic liquid 1-methyl-3-octylimidazolium chloride, [C8MIm][Cl]. Three commercially relevant polyaramids were synthesized: poly-p-phenylene terephthalamide (PPTA), poly-m-phenylene isophthalamide (PMIA) and copoly(p-phenylene/3,4′-diphenylether terephthalamide) (ODA/PPTA). PMIA was successfully synthesized in the OES containing [C8MIm][Cl] in a molar fraction ofxIL= 0.043, achieving an inherent viscosity ofηinh= 1.94 ± 0.064 dL g?1, which is on par with the current industrial standard and the benchmark lab scale synthesis. The reaction mixture could also be directly used for the wet spinning of polyaramid fibers, and all components of the solvent could be recycled in good yields by a series of evaporation and distillation steps. ODA/PPTA could be synthesized, but only rather low inherent viscosities were achieved. The reaction mixture was too viscoelastic to be spun by our small-scale spinning setup. PPTA always instantly precipitated and could not be synthesized from a [C8MIm][Cl]/GVL OES. α-Picoline, the organic base which was added to capture the released HCl during the reaction, was found to play a pivotal role in the polymerization reaction. By undergoing an acid-base reaction with HCl, it forms a protic ionic liquidin situwhich increases the solubility of the polymer.
- Winters, Jonas,Bolia, Raheed,Dehaen, Wim,Binnemans, Koen
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supporting information
p. 1228 - 1239
(2021/02/26)
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- Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant
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An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
- Yi, Xuewen,Yi, Xuewen,Lei, Siyu,Liu, Wangsheng,Che, Fengrui,Yu, Chunzheng,Liu, Xuesong,Wang, Zonghua,Zhou, Xin,Zhang, Yuexia
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supporting information
p. 4583 - 4587
(2020/05/05)
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- Synthesis of 2-Amino-1,3-dienes from Propargyl Carbonates via Palladium-Catalyzed Carbon-Nitrogen Bond Formation
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A catalytic method to synthesize 1,3,-dienes from propargylic precursors is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction furnishes 2-amino-1,3-dienes in excellent yields (up to 98%) and shows a broad tolerance to functional group diversity. The reaction has been demonstrated for over 30 amine substrates, including anilines and indoles, and proceeds under mild neutral conditions. The resulting 1,3-dienes are of great synthetic interest because of their further reaction potential.
- O'Broin, Calvin Q.,Guiry, Patrick J.
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supporting information
p. 879 - 883
(2020/02/04)
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- N-Phenylbenzamide derivatives as alternative oxidase inhibitors: Synthesis, molecular properties, 1H-STD NMR, and QSAR
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In the present work, 117 N-phenylbenzamides (NPDs) were prepared and evaluated against recombinant AOX from the fungal pathogen Moniliophthora perniciosa. 1H, 13C NMR, FTIR, and mass spectra provided structural information on NPDs. The library compounds were tested as Alternative Oxidase inhibitors in two different assays using the model yeast Pichia pastoris: cell growth and oxygen consumption assays. The most active compound, 3FH, was further characterized by DRX and 1H-NMR-STD. Single crystal X-ray diffraction showed intra- and intermolecular interactions of 3FH in solid-state and elucidated its 3D structural configuration. 1H-NMR-STD allowed us to derive protein-ligand interactions in a membrane-mimetic system and evidenced an outstanding interaction of 3FH with this enzyme. Results of both biological assays were used as input to Quantitative Structure-Activity Relationship models, which highlighted the more important molecular fragments contributions for protein-ligand interaction.
- Barsottini, Mario R. O.,Carazzolle, Marcelo F.,Costa, Paulo C. S.,Evangelista, Joel S.,Miranda, Paulo C. M. L.,Nascimento, Andrey F. Z.,Pereira, Gon?alo A. G.,Pires, Bárbara A.,Rocco, Silvana A.,Sfor?a, Maurício L.,Silva, Jaqueline S.,Vieira, Maria L. L.,Zeri, Ana C. M.
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- Synthesis of new phenolic compounds and biological evaluation as antiproliferative agents
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New series of phenolic azomethine compounds in addition to 5-arylidene thiazolidinones are synthesized and screened for their anticancer activity against the brain cancer cell line SNB-75 and non-small lung cancer cells HOP-92. The azomethine derivative 12b is the most active compound against SNB-75 displaying an IC50 value of 0.14 μM. Compounds 7b, 16a and 27d display submicromolar activity against the HOP-92 cell line with IC50 values of 0.73, 0.74 and 0.81 μM, respectively. Moreover, studying the cytotoxic effects of the most active compounds against normal lung cells WI-38 revealed that compounds 7b, 16a and 27d showed high safety profiles as anticancer agents.
- Ibrahim, Marwa A,George, Riham F,Abou-Seri, Sahar M,El-Moghazy, Samir M
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p. 181 - 192
(2020/01/06)
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- Decarboxylative/Oxidative Amidation of Aryl α-Ketocarboxylic Acids with Nitroarenes and Nitroso Compounds in Aqueous Medium
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The decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with 5-aryl-3-nitroisoxazole-4-carboxylates and substituted dinitrobenzenes under oxidative aqueous conditions to afford N-aryl amides is described. The reaction is suggested to proceed via a radical pathway in which a benzoyl nitroxyl radical, the key intermediate formed from reaction between nitroarene and benzoyl radical from glyoxalic acid, couples with hydroxyl radical from water to produce amide. Mechanistic insight allowed the scope of the strategy to be expanded to the synthesis of amides via reaction between aryl α-ketocarboxylic acids and nitroso compounds.
- Barak, Dinesh S.,Dahatonde, Dipak J.,Dighe, Shashikant U.,Kant, Ruchir,Batra, Sanjay
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supporting information
p. 9381 - 9385
(2020/11/30)
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- Design, synthesis, in-silico studies and biological screening of quinazolinone analogues as potential antibacterial agents against MRSA
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Type or The emergence of resistance to antibiotic has developed a complicated situation in the treatment of bacterial infections. Considering the antimicrobial resistance phenomenon as one of the greatest challenge of medicinal chemists for search of better anti-bacterial agents, which have potential narrow spectrum activity with low development of resistance potential and low toxicity to host. Cross-linking of peptidoglycan is a key step catalyze by Penicillin binding protein (PBP) to maintain integrity of cell wall in bacterial cell. However, these Penicillin binding protein (PBP) has developed resistance in methicillin-resistant Staphylococcus aureus (MRSA) due to acquisition of additional PBP2a. Various Quinazolinone analogues are reported in literature as potential anti-bacterial agents against MRSA. In present study new quinazolinone analogues has been designed, guided by molecular docking, In-silico and MM-GBSA study. Newly designed molecules have been synthesized by medicinal chemistry route and their characterization was done by using IR, NMR, & HR-MS techniques. Biological evaluation of synthesized compounds has been done on wild type Gram-negative (Escherichia coli), Gram-positive (Staphylococcus aureus) and resistant MRSA bacterial strains using Streptomycin, Kanamycin and Linezolid as standard drugs respectively. The in vitro evaluation results have shown that compound 5f is active with MIC value 15.625 μg/mL against S. aureus and with MIC value 31.25 μg/mL against MRSA.
- Qureshi, Shahnawaz I.,Chaudhari, Hemchandra K.
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supporting information
p. 2676 - 2688
(2019/05/17)
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- Probing 2H-Indazoles as Templates for SGK1, Tie2, and SRC Kinase Inhibitors
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The broader and systematic application of a novel scaffold is often hampered by the unavailability of a short and reliable synthetic access. We investigated a new strategy for the design and synthesis of an array of N2-substituted aza-2H-indazole derivatives as potential kinase inhibitors. Guided by a rational ligand alignment approach to qualify the so-far underrepresented aza-2H-indazole scaffold, indazoles were connected at the N2 position with a phenyl spacer and an arylsulfonamide or amide linkage. Initial profiling against a panel of 30 kinases confirmed the in silico predicted selectivity bias. A synthesized focused library of 52 different aza-2H-indazole derivatives showed good initial selective inhibition against SGK1, Tie2, and SRC kinases, with the best representatives having IC50 values in the range of 500 nm. In a comparative computational study, these data were analyzed and rationalized in light of docking studies.
- Schoene, Jens,Gazzi, Thais,Lindemann, Peter,Christmann, Mathias,Volkamer, Andrea,Nazaré, Marc
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p. 1514 - 1527
(2019/08/07)
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- Synthesis of Amides by Mild Palladium-Catalyzed Aminocarbonylation of Arylsilanes with Amines Enabled by Copper(II) Fluoride
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A general Pd-catalyzed synthesis of amides by oxidative aminocarbonylation of arylsilanes under mild conditions was accomplished for the first time. The reaction is promoted by a commercially available copper(II) fluoride, which acts as a dual silane activator and mild oxidant, enabling highly efficient aminocarbonylation of versatile arylsilanes at atmospheric CO pressure. The reaction is tolerant of a wide range of arylsilanes and various sensitive halide functional groups as well as a broad scope of amines are compatible with this oxidative process using cheap CO. A significant aspect involves the increased efficiency by the catalyst system. The reaction represents a segue into the powerful Pd-catalyzed oxidative transformations of organosilanes.
- Zhang, Jin,Hou, Yanyan,Ma, Yangmin,Szostak, Michal
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p. 338 - 345
(2019/01/10)
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- Mn(III)-mediated radical cascade reaction of boronic acids with isocyanides: Synthesis of diimide derivatives
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A manganese(III)-promoted oxidative radical cascade reaction of easily accessible arylboronic acids with isocyanides to construct diimide derivatives was studied. This protocol provides a new way to synthesis of acetyl diimide derivatives. New C–C, C–N and C[dbnd]O bonds were formed in one step.
- Wang, Fei,Wei, Tian-Qi,Xu, Pei,Wang, Shun-Yi,Ji, Shun-Jun
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supporting information
p. 379 - 382
(2018/09/11)
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- Method for preparing derivatives of benzamide under microwave condition in aqueous phase
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The invention discloses a method for preparing derivatives of benzamide under a microwave condition in an aqueous phase. A coupling reaction is carried out between substituted benzoic acid and amine under the microwave condition in the aqueous phase. The method for preparing the derivatives of benzamide is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applicable to a large number of functional groups, is high in yield, produces fewer by-products, and further is easy to operate, safe, low in cost and environmentally friendly. A formula is shown in the description.
- -
-
Paragraph 0019; 0048
(2019/03/28)
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- Pd-Catalyzed Oxidation of Aldimines to Amides
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Methods for the synthesis of amides via the direct oxidation of imines are rarely reported. Here we report an efficient method for Pd-catalyzed oxidation of imines to amide derivatives by the use of cheap aqueous tert -butyl hydroperoxide as an oxidant through a Wacker-type reaction. This method is practically convenient and displays high functional group tolerance, allowing a variety of imines to transform into the corresponding amide derivatives in moderate to good yields.
- Gao, Shanshan,Ma, Yaorui,Chen, Weidong,Luo, Junfei
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supporting information
p. 2191 - 2194
(2018/10/02)
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- Synthesis of nanomagnetic supported thiourea–copper(I) catalyst and its application in the synthesis of triazoles and benzamides
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A novel nanomagnetic supported thiourea–copper(I) complex and inorganic–organic Takemoto-like hybrid nanomagnetic catalyst was designed, and synthesized. The prepared naomagnetic catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, energy-dispersive X-ray analysis, transmission and scanning electron microscopies, thermogravimetry, nitrogen adsorption/desorption, zeta potential and vibrating sample magnetometry. Furthermore, the fabricated dual-role inorganic–organic hybrid catalyst shows a striking and robust catalytic activity for the synthesis of triazoles and benzamides through click and coupling reactions, respectively, under mild and eco-friendly reaction conditions.
- Mohammadi, Leila,Zolfigol, Mohammad Ali,Khazaei, Ardeshir,Yarie, Meysam,Ansari, Samira,Azizian, Saeid,Khosravi, Maryam
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- Latent Bronsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides
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Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N, N -dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Bronsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.
- Otsuka, Rikuto,Maruhashi, Kazuo,Ohwada, Tomohiko
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supporting information
p. 2041 - 2057
(2018/05/04)
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- Selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis
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The selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis is described. The reaction tolerates a broad range of functional groups, and the desired products were obtained in 10–95% yield.
- Wang, Jingjing,Li, Feng,Pei, Wenlong,Yang, Mixue,Wu, Yidan,Ma, Danyang,Zhang, Furong,Wang, Jianhui
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supporting information
p. 1902 - 1905
(2018/04/19)
-
- N-aryl secondary aryl amide synthetic method
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The invention discloses an N-aryl secondary aryl amide synthetic method. The synthetic method is characterized in that arylboronic acid and aromatic primary amine, and a main catalyst and a cocatalystare added in a solvent, then the components are subjected to a carbonylation reaction and then separation and purification to obtain the N-aryl secondary aryl amide, and CO is introduced into a reaction system during a reaction process so that the pressure of the reaction system is 0.1-5 MPa. The synthetic method is concise and efficient, aromatic amine and organic boric acid and CO which are stable in air and easily available can be taken as the reaction raw materials, under existence of the solvent, the catalysts are added, and the secondary aryl amide is synthesized with high efficiency under mild reaction condition.
- -
-
Paragraph 0112; 0113; 0114; 0115; 0116
(2018/03/28)
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- Synthesis of Secondary Amides through the Palladium(II)-Catalyzed Aminocarbonylation of Arylboronic Acids with Amines or Hydrazines and Carbon Dioxide
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A new Pd-catalyzed aminocarbonylation of arylboronic acids with amines or phenylhydrazines has been developed. Various secondary amides were produced from readily available substrates and cheap common metal catalysts in a CO atmosphere (balloon). Remarkably, we presents the first example of aminocarbonylations between arylboronic acids and phenylhydrazines.
- Zhang, Jin,Ma, Yuqiang,Ma, Yangmin
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supporting information
p. 1720 - 1725
(2018/04/24)
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- Design, synthesis and evaluation of azaacridine derivatives as dual-target EGFR and Src kinase inhibitors for antitumor treatment
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Overexpression of EGFR is often associated with advanced stage disease and poor prognosis. In certain cancers, Src works synergistically with EGFR to promote proliferation, survival, invasion and metastasis. Development of dual-target drugs against EGFR and Src is of therapeutic advantage against these cancers. Based on molecular docking and our previous studies, we rationally designed a new series of azaacridine derivatives as potent EGFR and Src dual inhibitors. Most of the synthesized azaacridines displayed good antiproliferative activity against K562 and A549?cells. The representative compound 13b showed nM IC50 values against K562 and A549?cells, and inhibited EGFR at inhibition rate of 33.53% at 10?μM and Src at inhibition rate of 72.12% at 1?μM. Furthermore, compound 13b could inhibit the expression of EGFR, p-EGFR, Src and p-Src. Moreover, 13b efficiently inhibited the invasion of tumor cells and induced cancer cells apoptosis. Our study suggested that azaacridine scaffold can be developed as novel multi-target kinase inhibitors for cancer therapy.
- Cui, Zhishan,Chen, Shaopeng,Wang, Yanwei,Gao, Chunmei,Chen, Yuzong,Tan, Chunyan,Jiang, Yuyang
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p. 372 - 381
(2017/05/19)
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- Palladium-Catalyzed Direct Synthesis of Phenanthridones from Benzamides through Tandem N–H/C–H Arylation
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We report a palladium-catalyzed method for the direct synthesis of phenanthridones from benzamides in a single step. Unlike previous reports, the current protocol does not need any directing groups or any harsh conditions. This methodology has a wide functional group tolerance therefore a series of phenanthridones were synthesized with a yield up to 87 %. The efficacy of this protocol was further explored by synthesizing some important naturally occurring amaryllidaceae alkaloids in a single step with very good yields.
- Banerji, Biswadip,Chatterjee, Satadru,Chandrasekhar,Nayan, Chinmay,Killi, Sunil Kumar
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supporting information
p. 5214 - 5218
(2017/09/29)
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- Aza-acridine compound and preparation method and application thereof
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The invention discloses a method for efficiently preparing an aza-acridine compound. The structural formula of the aza-acridine compound is shown as a formula I; the preparation method comprises the following steps: adding a 2-aminoquinoline-3-methanamide compound and a solvent under an air condition, and heating to reaction temperature; after the reaction is ended, separating and purifying to obtain multisubstituted acridine derivatives shown as the following formula, wherein the reaction temperature is 100 to 200DEG C, and the reaction time is 1 to 24 hours. A synthetic method of the aza-acridine compound, disclosed by the invention, has the advantages of scientificity, reasonability, simple and easily-operated synthesis process and high synthetic yield; a product is easy to purify. The invention also relates to the aza-acridine compound which can be used for inhibiting EGFR (Epidermal Growth Factor Receptor) and SrC, a preparation method of the aza-acridine compound, activity of a drug containing the aza-acridine compound and the application of the drug. The compound is shown in a formula II and can be used for preparing an EGFR and SrC activity inhibitor and a disease treatment medicine activated and mediated by the EGFR and the SrC.
- -
-
Paragraph 0103; 0193; 0194
(2017/07/21)
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- Fragmentation of Protonated N-(3-Aminophenyl)Benzamide and Its Derivatives in Gas Phase
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An ion of m/z 110.06036 (ion formula [C6H8NO]+; error: 0.32 mDa) was observed in the collision induced dissociation tandem mass spectrometry experiments of protonated N-(3-aminophenyl)benzamide, which is a rearrangement product ion purportedly through nitrogen-oxygen (N–O) exchange. The N–O exchange rearrangement was confirmed by the MS/MS spectrum of protonated N-(3-aminophenyl)-O18-benzamide, where the rearranged ion, [C6H8NO18]+ of m/z 112 was available because of the presence of O18. Theoretical calculations using Density Functional Theory (DFT) at B3LYP/6-31?g(d) level suggest that an ion-neutral complex containing a water molecule and a nitrilium ion was formed via a transition state (TS-1), followed by the water molecule migrating to the anilide ring, eventually leading to the formation of the rearranged ion of m/z 110. The rearrangement can be generalized to other protonated amide compounds with electron-donating groups at the meta position, such as, –OH, –CH3, –OCH3, –NH(CH3)2, –NH-Ph, and –NHCOCH3, all of which show the corresponding rearranged ions in MS/MS spectra. However, the protonated amide compounds containing electron-withdrawing groups, including –Cl, –Br, –CN, –NO2, and –CF3, at the meta position did not display this type of rearrangement during dissociation. Additionally, effects of various acyl groups on the rearrangement were investigated. It was found that the rearrangement can be enhanced by substitution on the ring of the benzoyl with electron-withdrawing groups. [Figure not available: see fulltext.]
- Zu, Chengli,Mukhopadhyay, Sukrit,Hanley, Patrick S.,Xia, Shijing,Bell, Bruce M.,Grigg, David,Gilbert, Jeffrey R.,O’Brien, John P.
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p. 917 - 926
(2016/05/02)
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- A quick Chan-Lam C-N and C-S cross coupling at room temperature in the presence of square pyramidal [Cu(DMAP)4I]I as a catalyst
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A rapid and efficient protocol for C-N and C-S cross coupling has been developed using a new square pyramidal copper complex, [Cu(DMAP)4I]I. The complex was successfully synthesized via a disproportionation reaction of CuI and DMAP in DMSO. The catalytic activity of the complex was found to be excellent for Chan-Lam coupling reaction between aryl boronic acid and amine, amide, azide or thiol. The reaction could be carried out in the presence of only 2 mol% of the copper catalyst in methanol at room temperature within a short time.
- Roy, Subhasish,Sarma, Manas Jyoti,Kashyap, Bishwapran,Phukan, Prodeep
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supporting information
p. 1170 - 1173
(2016/01/15)
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- Phosphine-free atmospheric carbonylation of aryl iodides with aniline derivatives in the presence of a reusable silica-supported palladium catalyst
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Various palladium catalysts were obtained by the immobilisation of palladium on silica, modified with imidazolium salts. The efficiency of the catalysts was greatly dependent on the choice of the anion of the imidazolium salt, the palladium precursor and on the conditions of heterogenisation. Palladium acetate immobilised on silica with grafted imidazolium chloride moieties was shown to be a selective and recyclable catalyst for atmospheric aminocarbonylation of aryl iodides with aromatic amines in DMF. It was proved that the greater loss of palladium in DMSO can be explained by the formation of soluble palladium complexes.
- Urbán, Béla,Papp, Máté,Srankó, Dávid,Skoda-F?ldes, Rita
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p. 150 - 157
(2015/02/19)
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- Photocatalytic synthesis of anilides from nitrobenzenes under visible light irradiation: 2 in 1 reaction
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An efficient method has been developed for the synthesis of a series of anilides via a two in one reaction of nitrobenzenes with anhydride in the presence of TiO2 as a nanocatalyst and photocatalyst under sunlight or blue LED irradiation. In this method simultaneously, nitrobenzenes convert to the corresponding anilines via photocatalytic reduction on the TiO2 surface, and a condensation of aniline with the anhydride performed on the Lewis acid site of the TiO2 surface. Interestingly amidation step leads to the promotion of better reaction and good selectivity in reduction of nitrocompounds. This method is simple, rapid, high yield, and green.
- Zand, Zahra,Kazemi, Foad,Partovi, Adel
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-
- Potent and selective inhibitors of the TASK-1 potassium channel through chemical optimization of a bis-amide scaffold
-
TASK-1 is a two-pore domain potassium channel that is important to modulating cell excitability, most notably in the context of neuronal pathways. In order to leverage TASK-1 for therapeutic benefit, its physiological role needs better characterization; however, designing selective inhibitors that avoid the closely related TASK-3 channel has been challenging. In this study, a series of bis-amide derived compounds were found to demonstrate improved TASK-1 selectivity over TASK-3 compared to reported inhibitors. Optimization of a marginally selective hit led to analog 35 which displays a TASK-1 IC 50 = 16 nM with 62-fold selectivity over TASK-3 in an orthogonal electrophysiology assay.
- Flaherty, Daniel P.,Simpson, Denise S.,Miller, Melissa,Maki, Brooks E.,Zou, Beiyan,Shi, Jie,Wu, Meng,McManus, Owen B.,Aubé, Jeffrey,Li, Min,Golden, Jennifer E.
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p. 3968 - 3973
(2014/09/03)
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- Copper catalyzed N-arylation between aryl halides and nitriles in water: An efficient tandem synthesis of benzanilides
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A series of benzanilide compounds were synthesized through copper-catalyzed tandem reactions. With the assistance of ionic liquid as phase transfer catalyst, aryl halides, and nitriles underwent a hydrolysis/coupling pathway to form benzanilides in water. Advantages of this reaction include the use of water as the environmental friendly solvent, short reaction time, and the tolerance of various functional groups. A proposed mechanism based on control experiments is also presented.
- Wang, Jichao,Yin, Xinchi,Wu, Jun,Wu, Datong,Pan, Yuanjiang
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p. 10463 - 10469
(2013/11/19)
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- Recyclable, highly efficient and low cost nano-MgO for amide synthesis under SFRC: A convenient and greener 'NOSE' approach
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A clean synthesis of amide derivatives has successfully been accomplished utilizing reusable nano-MgO under 'SFRC' (solvent free reaction condition). The 'green-ness' of this protocol makes it a benign alternative for the large scale synthesis.
- Das, Vijay Kumar,Devi, Rashmi Rekha,Thakur, Ashim Jyoti
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p. 118 - 125
(2013/06/26)
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- Highly selective mono-N-benzylation and amidation of amines with alcohols or carboxylic acids using the Ph2PCl/I2/imidazole reagent system
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Chlorodiphenylphosphine, imidazole, and molecular iodine in refluxing dichloromethane are used for the efficient preparation of amides under mild reaction conditions. This reagent system also shows excellent selectivity for mono-N-alkylation of amines with alcohols. In this system, the resulting phosphorus byproduct (diphenylphosphinic acid) is easily removed by extraction using an aqueous basic solution in the workup processes, which avoids the tedious and time-consuming chromatographic methods.
- Nowrouzi, Najmeh,Jonaghani, Mohammad Zareh
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experimental part
p. 498 - 509
(2012/07/30)
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- Continuous flow synthesis of secondary amides by tandem azidation-amidation of anilines
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The continuous flow synthesis of a variety of secondary amides by tandem azidation-amidation of anilines is described. This new procedure benefits from the improved safety feature of generating aromatic azides in flow, thus ensuring low concentrations of any potentially hazardous intermediates. The protocol was amenable to the production of multi-gram quantities of the amide product. Georg Thieme Verlag Stuttgart · New York.
- Spiteri, Christian,Moses, John E.
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p. 1546 - 1548
(2012/08/07)
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- Thermally induced cyclization of electron-rich N-arylthiobenzamides to benzothiazoles
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Heating N-(2-methoxyphenyl)benzenecarbothioamides in refluxing nitrobenzene for 24 hours gives the corresponding benzothiazoles with intramolecular ipso substitution of the ortho-methoxy substituent. The thermal cyclization of various other N-arylthiobenzamides is also explored. Georg Thieme Verlag Stuttgart · New York.
- Barrett, Oscene V.,Downer-Riley, Nadale K.,Jackson, Yvette A.
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experimental part
p. 2579 - 2586
(2012/09/07)
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- Molecular modeling studies, synthesis and biological evaluation of derivatives of N-phenylbenzamide as Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors
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The search for new antimalarial agents is necessary as current drugs in the market have become vulnerable due to the emergence of resistant strains of Plasmodium falciparum (Pf). The enzyme dihydroorotate dehydrogenase (PfDHODH) is a validated target for development of antimalarial agents. PfDHODH is a crucial enzyme in the de novo pyrimidine biosynthesis pathway and is essential for the growth of the parasite. In this article, we report the design, synthesis and evaluation of benzanilides as inhibitors of PfDHODH. From the pool of molecules designed using molecular modeling techniques, candidates were shortlisted for further evaluation based on docking scores and 3D-QSAR studies. The activities of these shortlisted analogs were predicted from CoMFA and CoMSIA models. The most promising molecules were synthesized using solvent-free microwave-assisted synthesis and their structures characterized by spectroscopic techniques. The molecules were screened for in vitro antimalarial activity by the whole cell assay method. Two molecules viz. KMC-3 and KMC-15 were found to be active at 8.7 and 5.7 μM concentrations, respectively. Springer Science+Business Media, LLC 2011.
- Desai, Kumar R.,Shaikh, Mushtaque S.,Coutinho, Evans C.
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experimental part
p. 321 - 332
(2012/06/01)
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- Elaborate ligand-based pharmacophore exploration and QSAR analysis guide the synthesis of novel pyridinium-based potent β-secretase inhibitory leads
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β-Secretase (BACE) inhibitors have potential as anti-Alzheimer's disease treatments prompting us to explore the pharmacophoric space of 129 known BACE inhibitors. QSAR analysis was employed to select optimal combination of pharmacophoric models and 2D physicochemical descriptors capable of explaining bioactivity variation (r2 = 0.88, F = 60.48, rLOO2 = 0.85, rPRESS2 against 25 external test inhibitors = 0.71). We were obliged to use ligand efficiency as the response variable because the logarithmic transformation of bioactivities failed to access self-consistent QSAR models. Three pharmacophoric models emerged in the successful QSAR equation suggesting at least three binding modes accessible to ligands within BACE binding pocket. QSAR equation and pharmacophoric models were validated through ROC curves and were employed to guide synthesis of novel pyridinium-based BACE inhibitors. The best inhibitor illustrated an IC50 value of 1.0 μM against BACE.
- Al-Nadaf, Afaf,Sheikha, Ghassan Abu,Taha, Mutasem O.
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experimental part
p. 3088 - 3115
(2010/07/08)
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- Copper-catalyzed synthesis of benzoxazoles via a regioselective C-H functionalization/C-O bond formation under an air atmosphere
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(Chemical Equation Presented) An efficient method for the synthesis of functionalized benzoxazoles is described that involves a copper(II)-catalyzed regioselective C-H functionalization/C-O bond formation protocol. The use of dichlorobenzene as a solvent at 160°C allows the use of air as the terminal oxidant in the catalytic synthesis of benzoxazoles in a process that has high functional group tolerance. The presence of a directing group at the meta position markedly improves the reaction efficacy and a variety of 7-substituted benzoxazoles are selectively produced under mild reaction conditions. The mechanism of the reaction is also discussed in this report.
- Ueda, Satoshi,Nagasawa, Hideko
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supporting information; experimental part
p. 4272 - 4277
(2009/09/08)
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- Brine-mediated efficient benzoylation of primary amines and amino acids
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Benzoylation of primary amines and amino acids is efficiently carried out in a brine solution using a stoichiometric amount of benzoyl chloride followed by trituration with aqueous saturated bicarbonate solution. Copyright Taylor & Francis Group, LLC.
- Chattopadhyay, Gautam,Chakraborty, Suchandra,Saha, Chandan
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experimental part
p. 4068 - 4075
(2009/04/11)
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- Study of reaction between triphenylphosphine and activated acetylenic esters in the presence of benzanilide and some its derivatives
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Triphenylphosphine reacts with dialkyl acetylenedicarboxylates in the presence of NH-acids, such as benzanilide, 2-cyanobenzanilide, N-(2-acetylphenyl)benzamide, 3-nitrobenzanilide and methyl 2-benzamidobenzoate to generate stable phosphorus ylides. These stable ylides exist in solution as a mixture of two geometrical isomers as a result of restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group.
- Hazeri, Nourollah,Maghsoodlou, Malek Taher,Khorassani, Sayyed Mostafa Habibi,Nassiri, Mahmoud,Afarini, Zahra
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experimental part
p. 97 - 100
(2009/07/18)
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- Rhodium-catalysed addition reaction of aryl- and alkenylboronic acids to isocyanates
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The addition reaction of aryl- and alkenylboronic acids to isocyanates is catalysed by a rhodium(i) complex, affording secondary amides under mild conditions. The Royal Society of Chemistry.
- Miura, Tomoya,Takahashi, Yusuke,Murakami, Masahiro
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p. 3577 - 3579
(2008/03/12)
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- A mild and efficient procedure for the conversion of aromatic carboxylic esters to secondary amides
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A mild and efficient procedure has been developed for the conversion of aromatic carboxylic esters to secondary amides using reusable Zn dust with microwave heating in the presence of N,N-dimethylformamide or conventional heating by stirring in an oil bath using THF as solvent. Zn dust can be reused several times after simple washing with dil. HC1 and distilled water.
- Arora, Revika,Paul, Satya,Gupta, Rajive
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p. 1137 - 1140
(2007/10/03)
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- N-Silylation of amines and amino acid esters under neutral conditions employing TMS-Cl in the presence of zinc dust
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An expedient synthetic approach to N-silylamines has been developed. The protocol, using TMS-Cl/zinc dust instead of BSA, is useful for the conversion of amines or amino acid esters to the corresponding silyl derivatives, followed by acylation with an acyl chloride or Fmoc-amino acid chloride to give the corresponding amide or peptide. This procedure, affording products in good to excellent yields, is also efficient for the coupling of sterically hindered amino acids like α,α-dialkylamino acids and NMe-amino acids. Further, the use of an equimolar quantity of organic base, such as Et 3N/pyridine, is circumvented.
- Suresh Babu, Vommina V.,Vasanthakumar, Ganga-Ramu,Tantry, Subramanyam J.
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p. 4099 - 4102
(2007/10/03)
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- The inhibition of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids
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Cyclic β-oxocarboxylic acids inhibit factor inhibiting hypoxia-inducible factor via ligation to the active site iron. The Royal Society of Chemistry 2005.
- Banerji, Biswadip,Conejo-Garcia, Ana,McNeill, Luke A.,McDonough, Michael A.,Buck, Matthew R. G.,Hewitson, Kirsty S.,Oldham, Neil J.,Schofield, Christopher J.
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p. 5438 - 5440
(2008/01/27)
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- PhCOCI-Py/basic alumina as a versatile reagent for benzoylation in solvent-free conditions
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A solvent-free procedure using PhCOCl-Py/basic alumina under microwave irradiation has been developed for N-, O- and S-benzoylation.
- Paul, Satya,Nanda, Puja,Gupta, Rajive
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p. 374 - 380
(2007/10/03)
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- Determination of aromaticity indices of thiophene and furan by nuclear magnetic resonance spectroscopic analysis of their anilides
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A series of m- and p-substituted anilides of benzoic acid, 2-thienoic acid, and 2-furoic acid were prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shifts of proton and carbon signals of the acyl aromatic rings and the Hammett σ. Plots of the chemical shift values of the carbonyl carbons of the benzanilides against those of the 2-thienamides and 2-furamides gave an excellent correlation and the values of the slopes are 0.79 and 0.52, respectively, in dimethyl sulfoxide-d6. The slopes could be considered as a set of aromaticity index.
- Lee, Chang Kiu,Yu, Ji Sook,Ji, Young Ran
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p. 1219 - 1227
(2007/10/03)
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- Design, anticonvulsive and neurotoxic properties of retrobenzamides / N- (nitrophenyl)benzamides and N-(aminophenyl)benzamides
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Design, anticonvulsant properties in maximal electroshock-reduced seizures [MES] and seizures reduced by subcutaneous administration of pentetrazole (scPtz), and neurotoxicity of retrobenzamides (N- (nitrophenyl)benzamides and N-(aminophenyl) benzamides are reported. These data are further compared with those on carbamazepine, phenytoin, ameltolide and other reference compounds. Studies on retrobenzamides in mice dosed intraperitoneally point out a good anticonvulsant potential in the MES test for the amino derivatives (N-(aminophenyl)benzamides) and moderate activity for corresponding 'nitro' derivatives. In rats dosed orally, aminoretrobenzamides were, however, less active in the MES test than in mice dosed intraperitoneally. Differences between experimental animal species and administration routes lead to hypothesize rapid metabolization of compounds, reduced intestinal resorption and increased removal from body. The presence of a methyl substitution on the N-phenyl moiety of aminoretrobenzamides attenuated these discrepancies between mice and rats. Present results indicate that pharmacological values - including the dose offering anticonvulsant protection in 50 % of tested animals (ED50) and protective indices - obtained on some retrobenzamides may compete with phenytoin and carbamazepine values. By contrast with phenytoin, some retrobenzamides further exhibit activity in the scPtz test.
- Bourhim, Mustapha,Poupaert, Jacques H.,Stables, James P.,Vallee, Louis,Vamecq, Joseph
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- AMIDINE DERIVATIVES WITH NITRIC OXIDE SYNTHETASE ACTIVITIES
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Amidine derivative compounds of formula I as defined in the Specification having nitric oxide synthetase inhibitory activity as well as processes for the preparation of and compositions containing said compounds are described
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- SN2 mechanism for alcoholysis, aminolysis, and hydrolysis of acetyl chloride
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First-order solvolysis rate constants are reported for solvolyses of acetyl chloride in methanol and MeOD, and in binary aqueous mixtures with acetone, acetonitrile, ethanol, methanol, and trifluoroethanol at 0°C. Product selectivities (S = [MeCOOR]/[MeCOOH] x [water]/[alcohol]) are reported for solvolyses in ethanol/ and methanol/water at 0°C. Solvolyses of acetyl chloride show a high sensitivity to changes in solvent ionizing power, consistent with C-Cl bond cleavage. As the solvent is varied from pure ethanol (or methanol) to water, S values and rate-rate profiles show no evidence for the change in reaction channel observed for solvolyses of benzoyl and trimethylacetyl chlorides. However, using rate ratios in 40% ethanol/water and 97% trifluoroethanol/ water (solvents of similar ionizing power but different nucleophilicities) to compare sensitivities to nucleophilic attack, solvolyses of acetyl chloride are over 20-fold more sensitive to nucleophilic attack than benzoyl chloride. The solvent isotope effect of 1.29 (MeOH/MeOD) for acetyl chloride is similar to that for p-methoxybenzoyl chloride (1.22) and is lower than for benzoyl chloride (1.55). Second-order rate constants for aminolyses of acetyl chloride with m-nitroaniline in methanol at 0°C show that acetyl chloride behaves similarly to p-methoxybenzoyl chloride, whereas benzoyl chloride is 40-fold more sensitive to the added amine. The results indicate mechanistic differences between solvolyses of acetyl and benzoyl chlorides, and an SN2 mechanism is proposed for solvolyses and aminolyses by m-nitroaniline of acetyl chloride (i.e. these reactions are probably not carbonyl additions, but a strong sensitivity to nucleophilic attack accounts for their high rates).
- Bentley, T. William,Llewellyn, Gareth,McAlister, J. Anthony
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p. 7927 - 7932
(2007/10/03)
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- SYNERGISM AS A TEST FOR KINETICALLY INDISTINGUISHABLE MECHANISMS OF NUCLEOPHILIC AND GENERAL-BASE CATALYSIS IN THE ACYLATION OF ARYLAMINES. CHECKING THE TEST
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Our previously proposed test for the identification of the kinetically indistinguishable mechanisms of nucleophilic and general-base catalysis in acyl transfer processes, based on the synergistic effect in the action of a pair of catalysts, was checked for the case of the reaction of benzoyl chloride with 3-nitroaniline in benzene and dioxane (25 deg C), catalyzed by organic bases.With tetrabutylammonium chloride as catalyst marker (in the general-base mechanism) it was established that pyridine N-oxide is a nucleophilic catalyst, and this agrees with the version proposed in the literature.It was then shown with two independent catalyst markers (tetrabutylammonium chloride and pyridine N-oxide) that 4-methylpyridine and triethylamine catalyze the process by the nucleophilic mechanism while ε-caprolactam and hexamethylphosphorotriamide catalyze it in the general-base mechanism.The large amount of information provided by the proposed test is emphasized.
- Savelova, V.A.,Belousova, I.A.,Simanenko, Yu. S.
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p. 247 - 254
(2007/10/02)
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- CATALYSIS BY TETRABUTOXYTITANIUM IN REACTIONS OF SUBSTITUTED ANILINES WITH BENZOIC ACID
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During the benzoylation of arylamines by benzoic acid in boiling o-xylene or trichlorobenzene, catalyzed by tetrabutoxytitanium, the N-arylbenzamides are formed with yields of up to 98percent.The reaction takes place with amino-, methoxy-, methyl-, halogeno-, and nitroanilines and 1-aminoanthraquinone. 4-Aminophenol does not react with benzoic acid.
- Shteinberg, L. Ya.,Kondratov, S. A.,Shein, S. M.
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p. 1758 - 1762
(2007/10/02)
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- EFFECT OF THE STRUCTURE OF CARBOXYLIC ACIDS ON THEIR CATALYTIC ACTIVITY IN THE ALCOHOLYSIS OF CARBOXYLIC ACID CHLORIDES BY 1-BUTANOL IN TOLUENE
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The kinetics of the reactions of butyryl chloride with 1-butanol in toluene, catalyzed by trimethylacetic, acetic, and monochloro- and trichloroacetic acids, were studied.It was shown that these acids hardly differ at all in catalytic activity, and the Taft constant was ρ* 0.The obtained data are compared with those for the alcoholysis of 3,5-dinitrobenzoyl chloride and trichloroacetyl chloride and also for certain aminolysis reactions.Details of the mechanism of bifunctional catalysis are amplified.
- Semenyuk, G. V.,Oleinik, N. M.,Razumova, N. G.,Zhil'tsov, N. P.
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p. 1225 - 1231
(2007/10/02)
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