103-71-9Relevant articles and documents
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Hoshino et al.
, p. 3097 (1952)
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CARBONYLATION OF NITROBENZENE WITH RUTHENIUM CLUSTERS
Basu, Amitabha,Bhaduri, Sumit,Khwaja, Hanif
, p. C28 - C30 (1987)
Evidence is presented for the participation of cluster intermediates in the carbonylation of nitrobenzene.
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Kurita,K. et al.
, p. 2070 - 2071 (1976)
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Preferred Binding of Carboxylates by Chiral Urea Derivatives Containing α-Phenylethyl Group
Cortés-Hernández, Mayra,Rojas-Lima, Susana,Hernández-Rodríguez, Marcos,Cruz-Borbolla, Julián,López-Ruiz, Heraclio
, p. 416 - 424 (2016)
An efficient, simple protocol for the synthesis of a new family of chiral ureas 1 – 4 is described. The binding properties of 1 – 4 toward different anion (acetate, benzoate, fluoride, and chloride) have been studied by1H-NMR titration and have been observed in the case of 4 is a selective receptor for acetate. The theoretical calculation M06/6-311+G(d,p) helped us explain the binding properties observed. The most interesting observation is that this calculated structure is consistent with expected, based on the concept of allylic 1,3-strain (A1,3strain). When chiral caboxylates were studied, urea 1 was the best in discriminating between enantiomers.
SYNTHESIS OF ISOCYANATES BY THE CARBONYLATION OF AROMATIC NITRO COMPOUNDS, AZOBENZENE, AND AZOXYBENZENE ON PALLADIUM CATALYSTS CONTAINING MOLYBDENUM AND VANADIUM
Lapidus, A. L.,Manov-Yuvenskii, V. I.,Petrovskii, K. B.
, p. 2282 - 2284 (1981)
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Manov-Yuvenskii,Nefedov
, (1979)
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The curtius rearrangement of acyl azides revisited - Formation of cyanate (R-O-CN)
Wentrup, Curt,Bornemann, Holger
, p. 4521 - 4524 (2005)
The Curtius rearrangement is a synthesis of isocyanates (R-N=C=O) by thermal or photochemical rearrangement of acyl acides and/or acylnitrenes. The photochemical rearrangement of benzoyl azide is now shown for the first time to produce a small amount of phenyl cyanate (Ph-O-CN) together with phenyl isocyanate. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
CATALYTIC CARBONYLATION OF NITRO COMPOUNDS IN THE PRESENCE OF CARBONYL IONIC COMPLEXES OF Rh(I), Ir(I), Pd(I), AND Pd(II)
Abakumov, G. A.,Knyazeva, I. L.,Vavilina, N. N.,Gorbunova, L. V.,Zhivtsova, S. V.
, p. 1242 - 1245 (1984)
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EFFECT OF CATALYST COMPOSITION AND REACTION CONDITIONS ON SYNTHESIS OF PHENYL ISOCYANATE BY CARBONYLATION OF NITROBENZENE
Manov-Yuvenskii, V. I.,Nefedov, B. K.,Smetanin, A. V.
, p. 1817 - 1819 (1980)
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Reactivity of Carbamoyl Radicals: the First General and Convenient Free-radical Synthesis of Isocyanates
Minisci, Francesco,Coppa, Fausta,Fontana, Francesca
, p. 679 - 680 (1994)
The first free-radical synthesis of isocyanates was performed by oxidation of oxalic acid monoamides by S2O82-, catalysed by silver(I) and copper(II) salts, in a two-phase system.
Synthesis and biological evaluation of novel 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives as potential antitumor agents
Hu, Min,Meng, Nana,Xia, Yong,Xu, Youzhi,Yu, Luoting,Zeng, Xiuxiu,Zhou, Shuyan
, (2021)
A novel series of 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives were synthesized and evaluated against different tumor cell lines. Experiments in vitro showed that these derivatives could inhibit the proliferation of two kinds of human cancer cell lines (HepG2, HCT116) at low micromolar concentrations and the most potent analog 5q possessed broad-spectrum antiproliferative activity. Experiments in vivo demonstrated that 5q could effectively prolong the longevity of colon carcinoma-burdened mice and slow down the progression of cancer cells by suppression of angiogenesis and the induction of apoptosis and necrosis.
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Hofmann,A. W.
, p. 655 (1870)
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Synthesis of new coumarin compounds and its hypoglycemic activity and structure-activity relationship
Qi, Gang,Zhang, Wenguo
, p. 9835 - 9839 (2013)
Novel coumarin compounds were designed and synthesized by combining the active moieties of hypoglycemic drugs. The coumarin compounds were made by sulfanilamide with isocynate, the intermediate sulfanilamide was formed from coumarin by chlorosulfonated and aminated. These targeted compounds were characterized by FT-IR, 1H NMR and MS spectra and their hypoglycemic activities were evaluated in mice. The preliminary results showed that some compounds exhibited evident hypoglycemic effect (P > 0.01, CMC-Na as negative control). The relationship between these compounds structure with their hypoglycemic activities were studied in order to design new antidiabetic agents.
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Magee,Daniels
, p. 829 (1957)
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Mukaiyama,T. et al.
, p. 4381 - 4384 (1961)
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Preparation and photocatalytic property of hexagonal cylinder-like bipods ZnO microcrystal photocatalyst
Liu, Yumin,Hua, Lv,Li, Shuangqing,Xing, Xinyan,Xi, Guoxi
, p. 443 - 449 (2012)
Single crystalline ZnO with hexagonal cylinder-like bipods morphologies were successfully synthesized via a cationic surfactant-assisted hydrothermal microemulsion route. The structure, morphologies and properties of the as-prepared samples were determined using X-ray diffraction, scanning electron microscopy, photoluminescence spectrum and Ultraviolet and Visible absorption spectroscopy. The photocatalytic activities of the obtained products were evaluated by the degradation of Reactive Brilliant Red K-2BP in aqueous solution under a variety of conditions. Under the optimum condition, approximately 99.5% decolorization efficiency within 45 min and 65.3% TOC removal efficiency within 3 h were achieved, which were higher than that by the commercial ZnO. Moreover, the degradation products were analyzed by a gas chromatography coupled with mass spectrometry system and the probable pathways for the formation of the intermediates were proposed. The photocatalytic results indicated that the as-prepared ZnO showed good photocatalytic activity and it could be considered as a promising photocatalyst for dyes wastewater treatment.
EFFECT OF SOLVENT AND TRANSITION-METAL OXIDE AND CHLORIDE ON CATALYST ACTIVITY IN PHENYL ISOCYANATE SYNTHESIS BY NITROBENZENE CARBOXYLATION
Manov-Yuvenskii, V. I.,Nefedov, B. K.
, p. 816 - 819 (1981)
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Bamberger,Destraz
, p. 1885 (1902)
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Thermal Decomposition of Benzoyl Azide and Diazoacetone in the Gas Phase
Prokudin, V. G.,Sipyagin, A. M.,Kartsev, V. G.,Vozchikova, S. A.
, p. 1541 - 1544 (1988)
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Coleman et al.
, p. 4534,4535 (1954)
Design, synthesis and structure-activity relationships of novel diaryl urea derivatives as potential EGFR inhibitors
Jiang, Nan,Bu, Yanxin,Wang, Yu,Nie, Minhua,Zhang, Dajun,Zhai, Xin
, (2016)
Two novel series of diaryl urea derivatives 5a-i and 13a-l were synthesized and evaluated for their cytotoxicity against H-460, HT-29, A549, and MDA-MB-231 cancer cell lines in vitro. Therein, 4-aminoquinazolinyl-diaryl urea derivatives 5a-i demonstrated significant activity, and seven of them are more active than sorafenib, with IC50 values ranging from 0.089 to 5.46 μM. Especially, compound 5a exhibited the most active potency both in cellular (IC50 = 0.15, 0.089, 0.36, and 0.75 μM, respectively) and enzymatic assay (IC50 = 56 nM against EGFR), representing a promising lead for further optimization.
Synthesis and Crystal Structure of , a Ruthenium Cluster with a Phenyl Isocyanate Ligand
Bhaduri, Sumit,Khwaja, Hanif,Jones, Peter G.
, p. 194 - 195 (1988)
The ruthenium cluster = (Ph3P)2N> has been synthesised by intramolecular nucleophilic attack on CO and characterised by X-ray structure determination.
Aminolysis of phenyl N-phenylcarbamate via an isocyanate intermediate: Theory and experiment
Ilieva, Sonia,Nalbantova, Didi,Hadjieva, Boriana,Galabov, Boris
, p. 6440 - 6449 (2013)
A comprehensive examination of the mechanism of the uncatalyzed and base-catalyzed aminolysis of phenyl N-phenylcarbamate by theoretical quantum mechanical methods at M06-2X/6-311+G(2d,2p) and B3LYP-D3/6-31G(d,p) levels, combined with an IR spectroscopic study of the reaction, was carried out. Three alternative reaction channels were theoretically characterized: concerted, stepwise via a tetrahedral intermediate, and stepwise involving an isocyanate intermediate. In contrast to dominating views, the theoretical results revealed that the reaction pathway through the isocyanate intermediate (E1cB) is energetically favored. These conclusions were supported by an IR spectroscopic investigation of the interactions of phenyl N-phenylcarbamate with several amines possessing varying basicities and nucleophilicities: n-butylamine, diethylamine, triethylamine, N-methylpyrrolidine, and trimethylamine. The reactivity of substituted phenyl N-phenylcarbamates in the aminolysis reaction was rationalized using theoretical and experimental reactivity indexes: electrostatic potential at nuclei (EPN), Hirshfeld and NBO atomic charges, and Hammett constants. The obtained quantitative relationships between these property descriptors and experimental kinetic constants reported in the literature emphasize the usefulness of theoretical parameters (EPN, atomic charges) in characterizing chemical reactivity.
Discovery of Potent EGFR Inhibitors With 6-Arylureido-4-anilinoquinazoline Derivatives
Li, Meng,Xue, Na,Liu, Xingang,Wang, Qiaoyun,Yan, Hongyi,Liu, Yifan,Wang, Lei,Shi, Xiaowei,Cao, Deying,Zhang, Kai,Zhang, Yang
, (2021/06/14)
According to the classical pharmacophore fusion strategy, a series of 6-arylureido-4-anilinoquinazoline derivatives (Compounds 7a–t) were designed, synthesized, and biologically evaluated by the standard CCK-8 method and enzyme inhibition assay. Among the title compounds, Compounds 7a, 7c, 7d, 7f, 7i, 7o, 7p, and 7q exhibited promising anti-proliferative bioactivities, especially Compound 7i, which had excellent antitumor activity against the A549, HT-29, and MCF-7 cell lines (IC50 = 2.25, 1.72, and 2.81?μM, respectively) compared with gefitinib, erlotinib, and sorafenib. In addition, the enzyme activity inhibition assay indicated that the synthesized compounds had sub-micromolar inhibitory levels (IC50, 11.66–867.1?nM), which was consistent with the results of the tumor cell line growth inhibition tests. By comparing the binding mechanisms of Compound 7i (17.32?nM), gefitinib (25.42?nM), and erlotinib (33.25?nM) to the EGFR, it was found that Compound 7i could extend into the effective region with a similar action conformation to that of gefitinib and interact with residues L85, D86, and R127, increasing the binding affinity of Compound 7i to the EGFR. Based on the molecular hybridization strategy, 14 compounds with EGFR inhibitory activity were designed and synthesized, and the action mechanism was explored through computational approaches, providing valuable clues for the research of antitumor agents based on EGFR inhibitors.
Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides
Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong
supporting information, p. 2820 - 2826 (2021/02/01)
A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.