6300-58-9Relevant academic research and scientific papers
Acyl Derivatives of Eudesmanolides To Boost their Bioactivity: An Explanation of Behavior in the Cell Membrane Using a Molecular Dynamics Approach
Mejías, Francisco J. R.,Durán, Alexandra G.,Zorrilla, Jesús G.,Varela, Rosa M.,Molinillo, José M. G.,Valdivia, Manuel M.,Macías, Francisco A.
, p. 1297 - 1307 (2021/02/09)
Semisynthetic analogs of natural products provide an important approach to obtain safer and more active drugs and they can also have enhanced physicochemical properties such as persistence, cross-membrane processes and bioactivity. Acyl derivatives of different natural product families, from sesquiterpene lactones to benzoxazinoids, have been synthesized and tested in our laboratories. These compounds were evaluated against tumoral and nontumoral cell lines to identify selective derivatives with a reduced negative impact upon application. The mode of action of these compounds was analyzed by anti-caspase-3 assays and molecular dynamics simulations with cell membrane re-creation were also carried out. Aryl derivatives of eudesmanolide stand out from the other compounds and are better than current anticancer drugs such as etoposide in terms of selectivity and activity. Computational studies provide evidence that lipophilicity plays a key role and the 4-fluorobenzoyl derivative can pass easily through the cell membrane.
Preparation method of symmetric disulfide bond-containing compound
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Paragraph 0020; 0045-0047, (2021/11/21)
The method comprises the following steps: adding a raw material and an oxidant to a reaction bottle containing a solvent; reacting 23W - 85W under the irradiation of 12 - 24h energy-saving lamps; and purifying the reaction product to obtain symmetrical disulfide bond-containing compounds. The raw material is mercaptan or thiophenol. The oxidizing agent is trichlorobromomethane, and the solvent is tetrahydrofuran. The method has the advantages of simple operation, high yield (70 - 90%), wide applicability, cheap and easily available raw materials, and provides a better way for the synthesis and production of symmetrical disulfide bond-containing compounds.
Synthesis of phenoxathiins and phenothiazines by aryne reactions with thiosulfonates
Hosoya, Takamitsu,Kanemoto, Kazuya,Sakata, Yuki,Yoshida, Suguru
supporting information, p. 593 - 596 (2020/05/19)
Novel synthetic methods for phenoxathiins and phenothiazines by aryne reactions are disclosed. We found that phenoxathiins were efficiently prepared by the reaction between aryne intermediates and S-(2-hydroxyaryl) 4-toluenethiosulfo-nates. A synthetic method for phenothiazines was also developed by the reaction of arynes with S-(2-aminoaryl) 4-toluenethiosulfonates.
An Organodiselenide with Dual Mimic Function of Sulfhydryl Oxidases and Glutathione Peroxidases: Aerial Oxidation of Organothiols to Organodisulfides
Rathore, Vandana,Upadhyay, Aditya,Kumar, Sangit
supporting information, p. 6274 - 6278 (2018/10/05)
A novel organodiselenide, which mimics sulfhydryl oxidases and glutathione peroxidase (GPx) enzymes for oxidation of thiols by oxygen and hydrogen peroxide, respectively, into disulfides has been presented. The developed catalyst oxidizes an array of organothiols into respective disulfides in practical yields by using aerial O2 to avoid any reagents/additives, base, and light source. The synthesized diselenide also catalyzes the reduction of hydrogen peroxide into water by following the GPx enzymatic catalytic cycle with a reduction rate of 49.65 ± 3.7 μM·min-1.
Magnetic iron oxide nanoparticles/K2S: a simple and scale-up method for the direct synthesis of symmetrical disulfides from aryl halides
Soleiman-Beigi, Mohammad,Mohammadi, Keivan,Mohammadi, Fariba
, p. 1545 - 1550 (2018/06/21)
A simple, one-pot, efficient and novel protocol has been developed for direct synthesis of symmetrical organic disulfides by domino reaction of aryl halides and K2S in the presence of magnetic Fe3O4 nanoparticles as a readily available, highly efficient and recyclable catalyst. A variety of diaryl disulfides can be obtained in good-to-excellent yields up to 98%.
A mild and efficient method for the conversion of aldehydes into nitriles and thiols into disulfides using an ionic liquid oxidant
Hosseinzadeh, Rahman,Golchoubian, Hamid,Nouzarian, Mahboobe
, p. 4713 - 4725 (2015/06/30)
A simple, mild and high yielding method for the conversion of various aldehydes to nitriles has been developed using an ionic liquid reagent, hexamethylene bis(N-methylimidazolium) bis(dichloroiodate) (HMBMIBDCI), in combination with aqueous ammonia in CH3CN at room temperature. Moreover, the treatment of aromatic and aliphatic thiols with HMBMIBDCI resulted in the corresponding disulfides in solvent-free condition at room temperature.
Aerobic oxidation of thioles to disulfides catalyzed by mixed-addenda vanadium (V) substituted heteropolyacids
Rezvani, M. A.,Harutyunyan, R.,Heravi, Majid M.
, p. 1232 - 1236,5 (2020/09/02)
The oxidation of thiols to related disulfides using mixed-addenda heteropolyacids as catalyst under mild condition has been studied. This system provides an efficient, convenient, and practical method for the syntheses of symmetrical disulfides. In this w
H5PV2Mo10O40 as an efficient catalyst for the oxidation of thiols to the corresponding disulfides using hydrogen peroxide as the oxidant
Shojaei, Abdollah Fallah,Rezvani, Mohamad Ali,Heravi, Majid
experimental part, p. 955 - 963 (2012/04/04)
The H5PV2Mo10O40 catalyzed the oxidation of thiols to their homodisulfides using hydrogen peroxide as the oxidant under mild conditions is reported. This system provides an efficient, convenient and practical me
Modifiable sulfur tethers as directing groups for aromatic C-H acetoxylation reactions
Richter, Heinrich,Beckendorf, Stephan,Mancheno, Olga Garcia
supporting information; experimental part, p. 295 - 302 (2011/04/16)
A designed new class of modifiable sulfur tethers for aromatic C-H bond functionalizations is presented. As a model, the palladium-catalyzed directed acetoxylation reaction was studied. The more challenging sulfoxide tethers were the most effective in this transformation, showing a broad functionality tolerance, high S oxido-redox stability and no catalyst poisoning. Preliminary mechanistic studies indicate that the higher reactivity and selectivity shown by the sulfoxide tethers vs. the corresponding sulfones can be attributed to an extra coordination of the sulfoxide S atom to the catalyst. The utility of the presented methodology to generate structurally interesting aromatic derivatives by a subsequent modification of the S-tether is also exemplified.
Efficient route for the preparation of benzyloxy-substituted benzenesulfonyl chlorides from mercaptophenols
Jumeaux, Coline,Cooper, David G.,Brown, Bruce T.,Forbes, Ian T.,Garzya, Vincenzo
scheme or table, p. 1805 - 1808 (2011/06/20)
A consistently high-yielding route has been developed for the preparation of benzyloxybenzenesulfonyl chlorides from mercaptophenols. This route allows rapid preparation of intermediates for array chemistry.
