97726-03-9Relevant articles and documents
Azobioisosteres of Curcumin with Pronounced Activity against Amyloid Aggregation, Intracellular Oxidative Stress, and Neuroinflammation
Hofmann, Julian,Ginex, Tiziana,Espargaró, Alba,Scheiner, Matthias,Gunesch, Sandra,Aragó, Marc,Stigloher, Christian,Sabaté, Raimon,Luque, F. Javier,Decker, Michael
, p. 6015 - 6027 (2021)
Many (poly-)phenolic natural products, for example, curcumin and taxifolin, have been studied for their activity against specific hallmarks of neurodegeneration, such as amyloid-β 42 (Aβ42) aggregation and neuroinflammation. Due to their drawbacks, arising from poor pharmacokinetics, rapid metabolism, and even instability in aqueous medium, the biological activity of azobenzene compounds carrying a pharmacophoric catechol group, which have been designed as bioisoteres of curcumin has been examined. Molecular simulations reveal the ability of these compounds to form a hydrophobic cluster with Aβ42, which adopts different folds, affecting the propensity to populate fibril-like conformations. Furthermore, the curcumin bioisosteres exceeded the parent compound in activity against Aβ42 aggregation inhibition, glutamate-induced intracellular oxidative stress in HT22 cells, and neuroinflammation in microglial BV-2 cells. The most active compound prevented apoptosis of HT22 cells at a concentration of 2.5 μm (83 % cell survival), whereas curcumin only showed very low protection at 10 μm (21 % cell survival).
On the synthesis and biological properties of isocombretastatins: A case of ketone homologation during Wittig reaction attempts
Stocker, Vivien,Ghinet, Alina,Leman, Marie,Rigo, Benoit,Millet, Regis,Farce, Amaury,Desravines, Deborah,Dubois, Joelle,Waterlot, Christophe,Gautret, Philippe
, p. 3683 - 3696 (2013/04/11)
New isocombretastatins were synthesized by reacting the corresponding phenstatin analogs with CH3PPh3Br in presence of tBuOK. These new derivatives showed significant activities against cellular proliferation and tubulin polymerization. In particular, monomethoxylated derivatives of phenstatin and isoCA-4 exhibit similar activities to those of parent phenstatin. Attempts of the Wittig reaction on 2- (or 4-) methoxy-4′-nitrobenzophenones in the same conditions do not lead to the expected isocombretastatins but to methyleneketones with the exclusion of triphenylphosphine. A mechanism for this new ketone homologation was proposed.
Synthesis, molecular modelling and biological evaluation of 4-amino-2(1H)-quinazolinone and 2,4(1H,3H)-quinazolidone derivatives as antitumor agents
Richter, Stephanie,Gioffreda, Barbara
experimental part, p. 810 - 820 (2012/03/08)
A series of 6-benzoyl-, 6-arylthio- and 6-arylsulfonyl-4-amino-2(1H)- quinazolinones and -2,4(1H,3H)-quinazolinediones were prepared. They were evaluated in vitro for their cytotoxicity against the NCI-60 cancer cell lines. A series of 6-benzoyl-, 6-arylthio- and 6-arylsulfonyl-4-amino-2(1H)- quinazolinones and -2,4(1H,3H)-quinazolinediones were prepared. They were evaluated in vitro for their cytotoxicity against the NCI-60 cancer cell lines. Copyright
Process for the preparation of substituted benzophenones
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, (2008/06/13)
There is provided an efficient and effective process for the preparation of a compound of formula I (I) 1via the acylation of the appropriate substituted benzene substrate in the presence of graphite, optionally in the presence of FeCl3. Compounds of formula I are useful as intermediates in the manufacture of agrichemical agents.
Immunotherapeutic agents
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, (2008/06/13)
Cyano and carboxy derivatives of substituted styrenes are inhibitors of tumor necrosis factor α, nuclear factor κB, and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions. A typical embodiment is 3,3-bis-(3,4-dimethoxyphenyl)acrylonitrile.
REACTIONS OF 4-CHLORO-1-NITROBENZENE WITH (3-CHLORO-4-METHOXYPHENYL)ACETONITRILE AND (3,4-DIMETHOXYPHENYL)ACETONITRILE; SYNTHESIS OF 8-CHLORO-1-METHYL (AND METHYLTHIOMETHYL)-6-(3,4-DISUBSTITUTED PHENYL)-4H-s-TRIAZOLO-1,4-BENZODIAZEPINES
Vejdelek, Zdenek,Holubek, Jiri,Budesinsky, Milos,Ryska, Miroslav,Svatek, Emil,Protiva, Miroslav
, p. 361 - 372 (2007/10/02)
Reactions of 4-chloro-1-nitrobenzene with (3-chloro-4-methoxyphenyl)acetonitrile and (3,4-dimethoxyphenyl)acetonitrile in methanolic potassium hydroxide gave the corresponding 3-aryl-5-chloro-2,1-benzisoxazoles Ia and Ib in good yields; compounds Va, Vb, VI-VIII, and X were isolated as by-products and identified by means of spectra.Compounds Ia and Ib were transformed in five steps to the title componds XVab and XVIab which were found inactive in tests for central depressant and anticonvulsant activity.