cas 6635-20-7, 5-Nitrovanillin | Articles data

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Method for producing entacapone
The present invention relates to an entacapone production method, which comprises a nitration reaction, a de-methylation reaction and a condensation reaction. The nitration reaction is completed by glacial acetic acid, vanillin and 65% nitric acid within 3-5 hours; the de-methylation reaction is completed by reaction among nitrovanillin, dichloromethane, tetrabutyl ammonium bromide, anhydrous aluminum chloride and pyridine; and the condensation reaction is completed by reaction among isopropanol, 3,4-dihydroxyl-5-nitro benzaldehyde, N,N-diethyl cyanoacetamide and piperidine. The entacapone production method provided by the invention is high in yield, high in purity and stable in quality.
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Paragraph 0041-0049

(2021/04/10)

Synthesis and biological activity of fibrate-based acyl- and alkyl-phenoxyacetic methyl esters and 1,2-dihydroquinolines
A series of highly potent antihyperlipidemic agents constituted by a fibrate-based structure was recently reported by our group, whose synthesis started from isovanillin derivatives. In the interest of evaluating the bioisosteric effect of the vanillin-based isomers on their antihyperlipidemic activity, the present study focuses on the synthesis of 5-acyl-1-phenoxyacetic methyl esters 5a–c and their saturated side-chain 5-alkyl-1-phenoxyacetates 6a–c. Their strong in vivo effect was associated with the inhibition of HMG-CoA reductase. Since 1,2-dihydroquinolines inhibit this enzyme, a series of such heterocycles (9a–d) was prepared by our efficient regioselective, one-step, solvent-free method. Apart from showing hypolipidemic activity in vivo, some of the compounds displayed antifungal, antioxidant and cytotoxic activity in vitro. The binding mode of four compounds at the active site of HMGRh was examined with docking simulations, observing an interaction with most of the amino acids targeted by simvastatin.
Chamorro-Cevallos, Germán,Cruz-López, María C.,Delgado, Francisco,Fuentes-Benites, Aydeé,Gómez-García, Omar,Gardu?o-Siciliano, Leticia,González-Romero, Carlos,Hernández-Benitez, Roberto I.,Jiménez, Fabiola,López, Julio,Madrigal, Damián A.,Mendieta, Aarón,Pucheta, Abraham,Ramírez-Villalva, Alejandra,Ramón-Gallegos, Eva,Romero, Liseth,Rosales-Acosta, Blanca,Rugerio-Escalona, Catalina,Sequeda-Juárez, Alfonso,Tamariz, Joaquín,Vázquez, Miguel A.,Villa-Tanaca, Lourdes
(2020/01/31)

Copper-mediated nitrosation: 2-nitrosophenolato complexes and their use in the synthesis of heterocycles
A simple protocol yielding ortho-substituted nitrosophenols from phenols is demonstrated, in the form of copper(II) bis(nitrosophenolato) complexes. The developed methodology was applied to a range of substrates, confirming the role of the copper in both the formation and protection of the challenging 1, 2-substitution pattern. Using polymer supported thiourea, the Cu could be stripped from the complexes and thus enabled the isolation or identification of the uncoordinated ligands and their decomposition products, in yields generally low in line with the intrinsic high reactivity of 2-nitrosophenols. The product complexes are useful intermediates as demonstrated in revisiting a formal [4 + 2] cycloaddition with dimethylacetylene dicarboxylate to synthesise bicyclic products in variable yields, revealing the product has a novel structure different from those previously reported in the literature.
Nicholls, Alexander J.,Batsanov, Andrei S.,Baxendale, Ian R.
(2019/11/28)

Method for preparing 5-nitrovanillin through nitrifying vanillin by nitrogen dioxide
The invention discloses a method for preparing 5-nitrovanillin through nitrifying vanillin by nitrogen dioxide. The method is characterized in that the vanillin and the nitrogen dioxide are stirred and reacted in the presence of a catalyst to obtain the 5-nitrovanillin. The nitrogen dioxide is used as a nitrifying reagent to substitute a nitric acid-acetic acid mixed acid nitrifying agent, so thecleanness of the above reaction is improved, and the environment pollution is reduced; the atom utilization rate and the atom economy property of the reaction are improved; reaction conditions are mild, the reaction is carried out in a nonacid medium, so waste acid treatment is avoided, the corrosion to a device is reduced, energy is saved, the emission is reduced, and the safety is high; and thecatalyst can be simply recovered, and can be reused multiple times.
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Paragraph 0011-0014

(2018/03/26)

a naked-eye colorimetric receptor for anions based on nitro group featuring with benzimidazole unit
A novel receptor based on nitro group featuring with benzimidazole unit (S2) was successfully synthesized and applied to the anion (CN–, F–and H2PO4–) recognition. The S2 changed its colour for light yellow to dark yellow on addition of the anions in DMSO solvent. The LOD and Kass values determined by UV-visible titration was 2.8 × 10–6 M and 1.2 (± 0.25) × 106 M–1 for CN– ion; 1.14 × 10–6 M and 2.5 (± 0.25) × 106 M–1 for F– ion; and 1.23 × 10–5 M and 6.25 (± 0.177) × 106 M–1 for H2PO4– ion, respectively.
Rahmawati,Purwono,Matsjeh
p. 1933 - 1936
(2018/08/09)

Yttrium Nitrate mediated Nitration of Phenols at room temperature in Glacial Acetic acid
Rapid nitration of electron rich phenols using Y(NO 3) 3.6H 2O in glacial acetic acid at room temperature was observed with good yield. The method allows nitration of phenols without oxidation, and isolation of nitration product in a rapid and simple way. The described method is selective for phenols. [Figure not available: see fulltext.]
Mondal, Mohabul A,Mandal, Debashis,Mitra, Kanchan
p. 39 - 43
(2017/01/24)

Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students
We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.
Chen, Hui-Zhen,Chen, You-Bao,Lv, Ya-Ping,Zeng, Fang,Zhang, Juan,Zhou, Yong-Lie,Li, Han-Bing,Chen, Li-Fei,Zhou, Bin-Jie,Gao, Jian-Rong,Xia, Chun-Nian
p. 4367 - 4371
(2015/02/06)

Synthesis and biological evaluation of cinnamido linked benzophenone hybrids as tubulin polymerization inhibitors and apoptosis inducing agents
A new class of hybrid molecules containing cinnamide subunit linked to benzophenone as inhibitors of tubulin polymerization were synthesized and evaluated for their anticancer potential. These hybrids exhibit anticancer activity with IC50 values ranging from 0.06 to 16.3 μM. Compounds 4f and 4g possessing fluoro and trifluoromethyl on the cinnamido subunit showed significant cytotoxic activity with IC50 values 0.06 and 0.09 μM against HeLa cell line, respectively. These compounds showed cell cycle arrest at G2/M phase of the cell cycle and inhibited tubulin polymerization followed by activation of caspase-3 activity and apoptotic cell death. Further in vitro tubulin polymerization assay showed that the level of tubulin inhibition was comparable to that of 2a for the compounds 4f and 4g. Moreover, Hoechst 33258 staining and DNA fragmentation assay suggested that these compounds induce cell death by apoptosis. Overall, the current study demonstrates that the synthesis of benzophenone linked cinnamide subunit conjugates as promising anticancer agents with G2/M arrest and apoptotic-inducing ability via targeting tubulin.
Kamal, Ahmed,Reddy, Ch. Ratna,Vishnuvardhan,Mahesh,Lakshma Nayak,Prabhakar,Reddy, C. Suresh
supporting information
p. 2309 - 2314
(2014/05/20)

Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases
The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a Ki-value of 35.7 μM at the Dengue and 44.6 μM at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively.
Nitsche, Christoph,Steuer, Christian,Klein, Christian D.
experimental part
p. 7318 - 7337
(2012/01/05)

Discovery of a long-acting, peripherally selective inhibitor of catechol- O -methyltransferase
Novel nitrocatechol-substituted heterocycles were designed and evaluated for their ability to inhibit catechol-O-methyltransferase (COMT). Replacement of the pyrazole core of the initial hit 4 with a 1,2,4-oxadiazole ring resulted in a series of compounds endowed with longer duration of COMT inhibition. Incorporation of a pyridine N-oxide residue at position 3 of the 1,2,4-oxadiazole ring led to analogue 37f, which was found to possess activity comparable to entacapone and lower toxicity in comparison to tolcapone. Lead structure 37f was systematically modified in order to improve selectivity and duration of COMT inhibition as well as to minimize toxicity. Oxadiazole 37d (2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4, 6-dimethylpyridine 1-oxide (BIA 9-1067)) was identified as a long-acting, purely peripheral inhibitor, which is currently under clinical evaluation as an adjunct to l-Dopa therapy of Parkinson's disease.
Kiss, László E.,Ferreira, Humberto S.,Torr?o, Leonel,Bonifácio, Maria Jo?o,Palma, P. Nuno,Soares-Da-Silva, Patrício,Learmonth, David A.
supporting information; experimental part
p. 3396 - 3411
(2010/09/05)

4-(3-Halo/amino-4,5-dimethoxyphenyl)-5-aryloxazoles and-N-methylimidazoles That Are cytotoxic against combretastatin a resistant tumor cells and vascular disrupting in a cisplatin resistant germ cell tumor model
New combretastatin A analogues featuring oxazole or N-methylimidazole bridged Z-alkenes and halo-or amino-substituted A-rings were tested against various cancer cell lines and in testicular germ cell tumor xenografts in mice. Imidazoles with 3-halo-4,5-dimethoxy substituted A-rings and 3-amino-4-methoxy substituted B-rings (7b and 8b) were efficacious at nanomolar concentrations against cells of combretastatin A refractory HT-29 colon carcinoma, multidrug-resistant MCF-7/Topo breast carcinoma, and cisplatin-resistant 1411HP testicular germ cell tumor. They induced apoptosis and inhibited tubulin polymerization. While well tolerated by mice at high doses, these imidazoles initiated extensive intratumoral hemorrhage and regressions of highly vascularized 1411HP xenografts.
Schobert, Rainer,Biersack, Bernhard,Dietrich, Andrea,Effenberger, Katharina,Knauer, Sebastian,Mueller, Thomas
body text
p. 6595 - 6602
(2010/11/19)

Mixed ligand cobalt(II) complex as an efficient catalyst for oxidative deoximation using hydrogen peroxide
Mixed ligand cobalt(II) complexes having an amino acid as a ligand are reported to catalyze the decomposition of hydrogen peroxide. This property was utilized for carrying out an easy and efficient deoximation of oximes to the corresponding carbonyl compounds.
Das, Pranab J.,Das, Amal,Baruah, Akashi
experimental part
p. 1140 - 1143
(2010/11/02)

Zeolite H-Y-supported copper(II) nitrate: A simple and effective solid-supported reagent for nitration of phenols and their derivatives
Highly regiospecific mononitration of phenols and substituted phenols is accomplished by employing copper(II) nitrate supported on a catalytic amount of zeolite H-Y in a solid state. Copyright Taylor & Francis Group, LLC.
Lalitha,Sivakumar
p. 1745 - 1752
(2008/09/20)

Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 μM, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 μM for CAPE against BEL-7404.
Xia, Chun-nian,Li, Hai-bo,liu, Feng,Hu, Wei-xiao
scheme or table
p. 6553 - 6557
(2009/09/06)

NEW PHARMACEUTICAL COMPOUNDS
Compounds of formula (I), wherein R1-R4, X, Y and Z are as defined in claims, exhibit COMT enzyme inhibiting activity and are thus useful as COMT inhibitors.
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Page/Page column 41-42

(2008/06/13)

Highly efficient nitration of phenolic compounds by zirconyl nitrate
Zirconyl nitrate was found to be an excellent reagent in the nitration of phenol and substituted phenols to give nitrated phenols. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity.
Selvam, J. Jon Paul,Suresh,Rajesh,Reddy, S. Ravinder,Venkateswarlu
p. 2507 - 2509
(2007/10/03)

p-Toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates
Highly regiospecific mononitration of phenols and substituted phenols is accomplished employing a metal nitrate and a catalytic amount of p-toluenesulfonic acid in acetone. An exclusive ortho-selectivity was observed with excellent yields. A variety of metal nitrates were used to obtain o-nitrophenols exclusively in good to excellent yields. The use of p-toluenesulfonic acid is key for the selectivity observed.
Anuradha,Srinivas,Aparna,Rao, J. Madhusudana
p. 4933 - 4935
(2007/10/03)

Nitration of aromatic compounds by Zn(NO3)2· 2N2O4 and its charcoal-supported system
Zn(NO3)2·N2O4 and its charcoal supported system were found to be efficient nitrating agents. Mononitration of aromatic compounds such as benzene, alkyl benzenes, halobenzenes, nitrobenzene, anisol, and the highly selective mono-, di-, and trinitration of phenol, and dinitraion of substituted phenols were also performed in the presence of these reagents.
Iranpoor, Nasser,Firouzabadi, Habib,Heydari, Reza,Shiri, Morteza
p. 263 - 270
(2007/10/03)

Synthesis and evaluation of bifunctional nitrocatechol inhibitors of pig liver catechol-O-methyltransferase
Bifunctional compounds were tested in vitro as potential inhibitors of pig liver catechol-O-methyltransferase (COMT) with respect to the catechol substrate 4-[(3,4-dihydroxyphenyl)azo]benzenesulfonate. The bifunctional compounds were a composite of either two nitrocatechols or one nitrocatechol and one phenol, linked by amide bonds to a spacer unit comprising two to five methylene groups. The unsymmetrical compounds N-[2-(4-hydroxybenzoylamine)ethyl]-3,4-dihydroxy-5- nitrobenzamide], N-[3-(4-hydroxybenzoyl-amine)propyl]-3,4-dihydroxy-5- nitrobenzamide] and N-[5-(4-hydroxybenzoylamine)pentyl]-3,4-dihydroxy-5- nitrobenzamide] demonstrated strong inhibitory action against COMT with K i values in the 100 nM range. In comparison, the monofunctional nitrocatechol analogues of these compounds had Ki values that were significantly higher.
Bailey, Karl,Tan, Eng Wui
p. 5740 - 5749
(2007/10/03)

Synthesis of condensed quinolines and quinazolines as DNA ligands
Among new condensed quinolines and quinazolines the design of which were inspired by anti-cancer DNA-binding alkaloids such as camptothecin and batracyclin, DNA binding tests identify the 8-methoxy-7- piperazinylpropoxyindeno[1,2-b]quinolin-11-one tetracyclic system as a new motif for DNA recognition.
Malecki, Natacha,Carato, Pascal,Rigo, Benoit,Goossens, Jean-Francois,Houssin, Raymond,Bailly, Christian,Henichart, Jean-Pierre
p. 641 - 647
(2007/10/03)

Synthesis and physico-chemical properties of nitrocaffeic acids
The synthesis and spectroscopic properties of the three isomers of nitrocaffeic acid are described. The three pKa s of each isomer were measured by UV-visible spectroscopy. The comparison of the UV-visible spectra of nitrocaffeic acids and those obtained from the reaction of caffeic acid with reactive nitrogen species led to the conclusion that the nitration of caffeic acid with acidic nitrite does not significantly occur and confirmed trie absence of nitration when caffeic acid reacts with peroxynitrite. Attempts to obtain free radical species from nitrocaffeic acids by classical methods showed a different reactivity to that of nitroaromatics and catechols. Nitrocaffeic acids do not autoxidize under aqueous basic conditions and are insensitive to t-BuOK or O2-. (two reactants known for their capabilities to oxidize catechols and reduce nitroaromatics). Nitroaromatic anion radicals may be obtained using sodium borohydride as reductant and are particularly stable under an uncontrolled atmosphere. Copyright
Grenier,Cotelle,Catteau,Cotelle
p. 511 - 517
(2007/10/03)

Isoquinoline compound melanocortin receptor ligands and methods of using same
The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.
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(2008/06/13)

Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel
The reaction of phenol with acetyl nitrate in chloroform gives nitrophenol with an ortho/para ratio of 1.8. This ratio increase to 13.3 when the reaction was carried out with acetyl nitrate pre-adsorbed on dry silica gel. Silica may be acting as a template to bring phenol close to acetyl nitrate by hydrogen bonds forming a ternary complex, which undergoes a six- center rearrangement to o-nitrophenol. The formation of this ternary complex is evaluated by ab initio molecular orbital calculation.
Augusto,Rodrigues,De Oliveira Filho, Antonio Pedro,Moran, Paulo J. S.,Custodio, Rogerio
p. 6733 - 6738
(2007/10/03)

Gas/Solid Reactions with Nitrogen Dioxide
Numerous gas/solid reactions of nitrogen dioxide with organic substrates are investigated preparatively and mechanistically.Gaseous NO2 reacts with crystalline stable free radicals (nitroxyls 1, verdazyl 6) by electron transfer.The nitrite ions formed are irreversibly oxidized by NO2 via oxygen atom transfer.Solid cation nitrates are formed quantitatively.Thione bonds of thiohydantoins 8 are transformed to carbonyl bonds with formation of sulfur and NO presumably via nitrites as intermediates.Hydantoin 13 oxygenates at its free 5-methylene group via C-H abstraction and nitrite or it undergoes N-1 nitration via N-H abstraction depending on the conditions.Both reactions proceed quantitatively. 1,3-Oxazolidin-2-one (15) gives N-nitration and N-nitrosation with the NO produced.Nonenolized crystalline barbituric acids 17 are quantitatively nitrated (C-N bond formation with radicals) at their methylene groups. 4-Hydroxybenzaldehyde (19) and vanilline (22) give quantitative aromatic nitration (C-N bond formation with arenes) without melting.All possible regioisomers are formed.Solid 9-methylanthracene (26) gives a quantitative yield of its 10-nitro derivative 27.Crystalline anthracene (28) and gaseous NO2 yield 3 primary products 29 (cis; trans) and the new dimeric product 30 as well as the stable secondary products 31 and 32.The gas/solid tetranitration of tetraphenylethylene (33) is severely hindered by the water of reaction.However, a 95percent yield of pure tetrakis(p-nitrophenyl)ethylene is obtained if the drying agent MgSO4*2H2O is admixed and the product 34 extracted.The gas/solid procedures avoid solvents and fuming nitric acid.They give pure products without necessity for recrystallization in most cases and they avoid wastes.Atomic force microscopy (AFM) measurements on prominent faces of single crystals of 1a, 11a, 28, and 33 reveal phase rebuildings with well-directed long-range molecular transport.Nanoliquids were only present on (110) of 28.The characteristic AFM features are correlated with known X-ray crystal structure data and compared with previous results.The shape of the features depends on the molecular packing in the crystal bulk and on the molecular shapes.Molecular interpretations of the AFM features are given.
Kaupp, Gerd,Schmeyers, Jens
p. 5494 - 5503
(2007/10/02)

TOTAL SYNTHESIS OF MAYTANSINOIDS. APPROACH TO 4,6-BISDEMETHYLMAYTANSINE AND 4-DEMETHYLMAYTANSINE
A convergent strategy was elaborated to synthesize maytansine 1 and maytansinoids modified on the carbon skeleton, especially 4-demethylmaytansine 2, 6-demethylmaytansine 3, 4,6-bisdemethylmaytansine 4.In this paper, the feasibility of the project was verified by the preparation of key intermediates for the synthesis of 4,6-bisdemethylmaytansine and 6-demethylmaytansine.The C-1-N open chain compound 18 in the 4,6-bisdemethyl series was obtained.
Benechie, Michel,Delpech, Bernard,Khuong-Huu, Qui,Khuong-Huu, Francoise
p. 1895 - 1910
(2007/10/02)

KINETICS AND MECHANISM OF SUBSTITUTIVE NITRATION OF GUAIACOL DERIVATIVES WITH DILUTE NITRIC ACID
The kinetics of the nitration reactions of a series of compounds which model the guaiacylpropane unit of lignin (vanillin, vanillic acid, and vanillic alcohol) to dinitroguaiacol by dilute nitric acid and aqueous sulfuric-nitric acid mixtures were investigated.It was shown that the substitution of the functional groups at the para position to the hydroxyl by a nitro group does not include an intermediate nitrosation stage but takes place by a free-radical mechanism, involving the formation and dissociation of nitroquinolide compounds.
Bazanova, G. V.,Stotskii, A. A.
p. 1845 - 1850
(2007/10/02)