27738-46-1Relevant articles and documents
Effect of a substituent on an aromatic group in diastereomeric resolution
Kinbara, Kazushi,Oishi, Koji,Harada, Yoshiko,Saigo, Kazuhiko
, p. 6651 - 6655 (2000)
The diastereomeric resolution of p-substituted 1-arylethylamines by enantiopure (S)-3',4'-methylenedioxymandelic acid ((S)-2) was carried out in order to know how an electron-donating or -withdrawing group on the aromatic group of the racemic amines would affect the efficiency of resolution. As a result, it was found that 1-arylethylamines having an electron-withdrawing substituent could be efficiently resolved by (S)-2, while the amines having an electron-donating group could not. The crystal structures of the less- and more-soluble salts, and the molecular orbital calculations of the ammonium cations indicated that the p-substituted electron-withdrawing group enhanced the positive charge on the meta-hydrogen of the aromatic group of the ammonium cations, which is favorable for the formation of a CH···π interaction in crystal. (C) 2000 Elsevier Science Ltd.
Structure-activity relationships, biological evaluation and structural studies of novel pyrrolonaphthoxazepines as antitumor agents
Brindisi, Margherita,Ulivieri, Cristina,Alfano, Gloria,Gemma, Sandra,de Asís Balaguer, Francisco,Khan, Tuhina,Grillo, Alessandro,Chemi, Giulia,Menchon, Grégory,Prota, Andrea E.,Olieric, Natacha,Lucena-Agell, Daniel,Barasoain, Isabel,Diaz, J. Fernando,Nebbioso, Angela,Conte, Mariarosaria,Lopresti, Ludovica,Magnano, Stefania,Amet, Rebecca,Kinsella, Paula,Zisterer, Daniela M.,Ibrahim, Ola,O'Sullivan, Jeff,Morbidelli, Lucia,Spaccapelo, Roberta,Baldari, Cosima,Butini, Stefania,Novellino, Ettore,Campiani, Giuseppe,Altucci, Lucia,Steinmetz, Michel O.,Brogi, Simone
, p. 290 - 320 (2018/11/24)
Microtubule-targeting agents (MTAs) are a class of clinically successful anti-cancer drugs. The emergence of multidrug resistance to MTAs imposes the need for developing new MTAs endowed with diverse mechanistic properties. Benzoxazepines were recently identified as a novel class of MTAs. These anticancer agents were thoroughly characterized for their antitumor activity, although, their exact mechanism of action remained elusive. Combining chemical, biochemical, cellular, bioinformatics and structural efforts we developed improved pyrrolonaphthoxazepines antitumor agents and their mode of action at the molecular level was elucidated. Compound 6j, one of the most potent analogues, was confirmed by X-ray as a colchicine-site MTA. A comprehensive structural investigation was performed for a complete elucidation of the structure-activity relationships. Selected pyrrolonaphthoxazepines were evaluated for their effects on cell cycle, apoptosis and differentiation in a variety of cancer cells, including multidrug resistant cell lines. Our results define compound 6j as a potentially useful optimized hit for the development of effective compounds for treating drug-resistant tumors.
Novel synthesis method of sesamol
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Paragraph 0026; 0030; 0037; 0044; 0051, (2018/11/22)
The invention discloses a novel synthesis method of sesamol. The method specifically comprises the following steps: first, gamma-glycidyl oxypropyl trimethoxysilane is used as a dispersing agent to prepare modified mullite powder; then, the modified mullite powder is used as a carrier to prepare a supported catalyst; catechol and dichloromethane are used as raw materials to prepare 1,3-benzodioxole under the catalysis of the supported catalyst; glyoxylic acid, a sulfuric acid solution and 1,3-benzodioxole are used as raw materials to obtain 3,4-methylenedioxy phenyl glycolic acid; the 3,4-methylenedioxy phenyl glycolic acid reacts with a nitric acid solution to prepare piperonal; finally, the piperonal and MCPBA react to prepare the sesamol. The method disclosed in the invention is simpleto operate, low in preparation cost and high in product yield.
Method for preparing heliotropin
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Paragraph 0011, (2017/08/27)
The invention discloses a method for preparing heliotropin. The preparation method comprises the following steps: (a) preparing dilute sulfuric acid from concentrated sulfuric acid and water, adding the dilute sulfuric acid into a flask, adding glyoxylic acid, and cooling the mixed solution by using ice water; (b) adding benzodioxole into the mixed solution in a certain period of time, reacting for some time at the temperature of 0 DEG C, diluting by using water, separating out the precipitate, filtering, washing, drying in the shade, thereby obtaining white 3,4-methylenedioxymandelic acid; and (c) adding the 3,4-methylenedioxymandelic acid and dilute nitric acid into the three-neck flask, heating and stirring in a boiling water bath for some time, extracting by using diethyl ether, taking the organic phase, neutralizing and washing by using aqueous solution of sodium hydroxide, and finally, drying the organic phase by using anhydrous sodium sulfate, boiling off the organic solvent, cooling to obtain solids, recrystallizing by using methanol, thereby obtaining the heliotropin crystals. The method disclosed by the invention is fewer in preparation processes, low in input cost, good in yield effect and safe to operate, has excellent prospects and is suitable for large-scale industrial production.
Preparation and reactions of certain racemic and optically active cyanohydrins derived from 2-chlorobenzaldehyde, 4-fluorobenzaldehyde, benzo[d][1,3]-dioxole-5-carbaldehyde and 2,3-dihydrobenzo[b][1,4]dioxine-6-carbaldehyde. Antimicrobial and in vitro antitumor evaluation of the products
Yosef, Hisham Abdallah A.,Elmasry,Ibrahim, Nabila M.,Ismael, Eman H. I.,Mahran
, p. 301 - 328 (2017/06/08)
THE CHEMOENZYMATIC reaction of selected aldehydes, namely 2-chlorobenzaldehyde (1a), 4-fluorobenzaldehyde (1b), benzo[d][1,3]dioxole-5-carbaldehyde (1c) and/or 2,3-dihydrobenzo [b] [1,4] dioxine-6-carbaldehyde (1d) with hydrogen cyanide in presence of (R)-oxynitrilase (R)-Pa HNL [EC 4.1.2.10] from almonds, as a chiral catalyst, gave the optically active cyanohydrin enantiomers ( R)-2a-c, respectively. Acetone cyanohydrin (3), was also used, as a transcyanating agent, to give the same products. The racemic cyanohydrins (R,S)-2a-d have been synthesized, as well, by treating compounds 1a-d with aqueous potassium cyanide solution in presence of a saturated solution of sodium metabisulphite (Na2S2O5). The optical purity of cyanohydrins (R)-2a-c was determined through their derivatization with (S)-naproxen chloride (S)-5 to the respective diastereomers (R,2S)-6a-c which were obtained in diastereomeric excess (de) values up to 93 % (1H NMR). Heating compounds (R)-2a,b and / or their racemic analogues (R,S)-2a-c with concentrated hydrochloric acid gave the respective α-hydroxycarboxylic acids 7a-c. Moreover, reduction of cyanohydrins (R,S)-2b,c under different conditions resulted in a hydrodecyanation giving the respective primary alcohols 8a,b. Structures and configurations of the new compounds were confirmed with compatible elementary microanalyses and spectroscopic (IR, 1H NMR, 13C NMR, MS and single crystal X-ray crystallography) measurements. The antimicrobial activity of derivatives 6a-d against four bacterial species (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa) and two fungi (Aspergillus flavus and Candida albicans) were undertaken. Moreover, compounds (R,2S)-6b, (R,2S)(S,2S)-6b and (R,2S)-6c were screened for their in virto antitumor activity against three human solid cancer cell lines (HCT 116, HepG2 and MCF-7). In general, the tested compounds were found inactive or showed weak activities in comparison with the standard drugs.
Sesamol intermediate product process for preparing Piperonal and application
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Paragraph 0025 - 0027, (2017/02/09)
The invention belongs to the field of food additives and provides a preparation method of a sesamol intermediate heliotropin. The preparation method is convenient to use by taking nitric acid as a decarboxylating agent; the product, namely the sesamol intermediate heliotropin is good in purity; especially the decarboxylation efficiency is high, so that the decarboxylation reaction can be efficiently carried out to directly influence the synthesis yield of the overall preparation route; compared with other synthesis routes, the heliotropin synthesis route disclosed by the invention has considerable advantage on the cost, and the product competitiveness is relatively strong. The synthesis method disclosed by the invention has the advantages of cheap raw materials, simple reaction process and high yield and can be applied to large-scale synthesis of sesamol.
Process for the preparation of 3,4-methylenedioxymandelic acid
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, (2008/06/13)
A process for preparing 3,4-methylenedioxymandelic acid by reacting 1,2-methylenedioxybenzene with glyoxylic acid in the presence of a strong acid and of at least one substance selected from the group consisting of an aprotic organic solvent and 100 to 1200 ml of an organic acid per kg of 1,2-methylenedioxybenzene.
High selectivity in the oxidation of mandelic acid derivatives and in 0-methylation of protocatechualdehyde: New processes for synthesis of vanillin, iso-vanillin, and heliotropin
Bj?rsvik, Hans-Rene?,Liguori, Lucia,Minisci, Francesco
, p. 534 - 543 (2013/08/07)
New synthetic procedures for vanillin, iso-vanillin, heliotropin, and protocatechualdehyde starting from catechol are described. The utilisation of statistical experimental design and multivariate modelling and the mechanistic interpretation of the acid and base catalysis in the condensation of catechol derivatives with glyoxylic acid and in the regiocontrolled methylation of protocatechualdehyde and of the Cu(II) salt catalysis in the oxidative decarboxylation of mandelic acid derivatives have allowed the development of new highly selective processes.
Cephalosporin derivatives
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, (2008/06/13)
The present invention relates to a compound represented by the structural formula: STR1 or its pharmaceutically acceptable salt or ester, which is a novel optically active compound useful as a curing agent for bacterial infections, a process for production thereof and a use thereof.
