6635-20-7Relevant academic research and scientific papers
Method for producing entacapone
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Paragraph 0041-0049, (2021/04/10)
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.
Synthesis and biological activity of fibrate-based acyl- and alkyl-phenoxyacetic methyl esters and 1,2-dihydroquinolines
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)
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.
Copper-mediated nitrosation: 2-nitrosophenolato complexes and their use in the synthesis of heterocycles
Nicholls, Alexander J.,Batsanov, Andrei S.,Baxendale, Ian R.
, (2019/11/28)
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.
Method for preparing 5-nitrovanillin through nitrifying vanillin by nitrogen dioxide
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Paragraph 0011-0014, (2018/03/26)
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.
a naked-eye colorimetric receptor for anions based on nitro group featuring with benzimidazole unit
Rahmawati,Purwono,Matsjeh
, p. 1933 - 1936 (2018/08/09)
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.
Yttrium Nitrate mediated Nitration of Phenols at room temperature in Glacial Acetic acid
Mondal, Mohabul A,Mandal, Debashis,Mitra, Kanchan
, p. 39 - 43 (2017/01/24)
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.]
Synthesis and biological evaluation of cinnamido linked benzophenone hybrids as tubulin polymerization inhibitors and apoptosis inducing agents
Kamal, Ahmed,Reddy, Ch. Ratna,Vishnuvardhan,Mahesh,Lakshma Nayak,Prabhakar,Reddy, C. Suresh
supporting information, p. 2309 - 2314 (2014/05/20)
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.
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
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)
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.
Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases
Nitsche, Christoph,Steuer, Christian,Klein, Christian D.
experimental part, p. 7318 - 7337 (2012/01/05)
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.
Discovery of a long-acting, peripherally selective inhibitor of catechol- O -methyltransferase
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)
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.
