33693-48-0Relevant academic research and scientific papers
Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols
Nagasawa, Shota,Fujiki, Shogo,Sasano, Yusuke,Iwabuchi, Yoshiharu
, p. 6952 - 6968 (2021/05/29)
We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.
Copper-nickel mixed oxide catalysts from layered double hydroxides for the hydrogen-transfer valorisation of lignin in organosolv pulping
Albonetti, Stefania,Awan, Iqra Zubair,Beltrami, Giada,Bonincontro, Danilo,Cacciaguerra, Thomas,Cavani, Fabrizio,Di Renzo, Francesco,Gimello, Olinda,Martucci, Annalisa,Tanchoux, Nathalie
, (2020/12/02)
Copper and nickel mixed catalysts obtained by calcination of iron and aluminium hydrotalcites (layered double hydroxides, LDH) have been tested in the conversion of a lignin model dimer in subcritical methanol. Phase distribution and textural properties of the catalysts were characterized by X-ray diffraction Rietveld analysis and N2 physisorption. The presence of copper was critical for effective hydrogenation, both by direct hydrogen transfer from methanol to aldehyde groups and by reactivity of products from methanol reforming. TPR experiments showed that the hydrogenation activity was promoted by an enhanced reducibility of the Cu-catalysts, related to the presence of other oxide components. Characterisation of the catalysts after reaction indicated that metallic copper was formed by the reduction of CuO by methanol and that modifications of the oxide catalysts in the reaction medium played a major role in the formation of active sites.
Structure-based design, docking and binding free energy calculations of a366 derivatives as spindlin1 inhibitors
Luise, Chiara,Robaa, Dina,Regenass, Pierre,Maurer, David,Ostrovskyi, Dmytro,Seifert, Ludwig,Bacher, Johannes,Burgahn, Teresa,Wagner, Tobias,Seitz, Johannes,Greschik, Holger,Park, Kwang-Su,Xiong, Yan,Jin, Jian,Schüle, Roland,Breit, Bernhard,Jung, Manfred,Sippl, Wolfgang
, (2021/06/03)
The chromatin reader protein Spindlin1 plays an important role in epigenetic regulation, through which it has been linked to several types of malignant tumors. In the current work, we report on the development of novel analogs of the previously published lead inhibitor A366. In an effort to improve the activity and explore the structure–activity relationship (SAR), a series of 21 derivatives was synthesized, tested in vitro, and investigated by means of molecular modeling tools. Docking studies and molecular dynamics (MD) simulations were performed to analyze and rationalize the structural differences responsible for the Spindlin1 activity. The analysis of MD simulations shed light on the important interactions. Our study highlighted the main structural features that are required for Spindlin1 inhibitory activity, which include a positively charged pyrrolidine moiety embedded into the aromatic cage connected via a propyloxy linker to the 2-aminoindole core. Of the latter, the amidine group anchor the compounds into the pocket through salt bridge interactions with Asp184. Different protocols were tested to identify a fast in silico method that could help to discriminate between active and inactive compounds within the A366 series. Rescoring the docking poses with MM-GBSA calculations was successful in this regard. Because A366 is known to be a G9a inhibitor, the most active developed Spindlin1 inhibitors were also tested over G9a and GLP to verify the selectivity profile of the A366 analogs. This resulted in the discovery of diverse selective compounds, among which 1s and 1t showed Spindlin1 activity in the nanomolar range and selectivity over G9a and GLP. Finally, future design hypotheses were suggested based on our findings.
KETONES AND METHOD FOR MANUFACTURING ANALOG THEREOF
-
Paragraph 0070-0074, (2019/04/05)
PROBLEM TO BE SOLVED: To provide a technique for efficiently producing ketones by using cellulose after extracting chitin and chitosan extracted from the crustacean or sucrose from the beet in order to effectively using wastes, such as a crustacean or a beat to prepare a solid catalyst. SOLUTION: A method for manufacturing 1-phenyl-3-ketones and an analog (a compound 3) comprises using at least one kind selected from a group consisting of cellulose, chitin and chitosan as a carrier and reacting benzyl alcohols (a compound 1) with ketones (a compound 2) in the presence of a solid catalyst obtained by supporting a group 8-10 transition metal and a base. The following chemical formula 1 is shown. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
Versatile and Enantioselective Total Synthesis of Naturally Active Gnetulin
Shang, Changhui,Kang, Yulong,Yang, Qingyun,Zhu, Qibin,Yao, Chunsuo
, p. 3768 - 3776 (2019/07/12)
A versatile and efficient enantioselective total synthesis of natural isorhapontigenin dimers (?)-gnetulin, (+)-gnetulin, and (±)-gentulin was proposed. By using this method, we were able to synthesize the dimers from commercial available achiral materials in 13 steps, and achieve a 7%–9% overall yield with >98% enantiomeric excess. The key features of the method include the stereocontrolled enantioselective conjugate reduction of 3-arylindenone catalyzed by methyloxazaborolidine (Me-CBS) and the α-arylation of 3-aryl-1-indanones. Benzylic sulfide was accessed in excellent yield through the InCl3-catalyzed thio-etherification reaction between 2,3-diarylindanol and bezylic thiol. The method is practical and might thus be useful in the enantioselective synthesis of the optical antipodes of natural indane derivatives with or without methoxy groups at aromatic rings. (Figure presented.).
Synthesis of phenolic components of Grains of Paradise
Hattori, Hiroyuki,Mitsunaga,Clive, Derrick L.J.
supporting information, p. 1989 - 1991 (2019/07/03)
Two vanilloids, (5E)-8-(4-hydroxy-3-methoxyphenyl)oct-5-en-4-one (1) and 4-[3-hydroxydecyl]-2-methoxyphenol (2), isolated from the dried seeds of Grains of Paradise (Aframomum melegueta), were synthesized; the latter compound was made as the S-enantiomer and the material derived from the seeds was found to be a 1:1.7 mixture of the R and S isomers. The synthetic route used should allow the preparation of analogs having extended alkyl chains and consequently different lipophilicity, and 3, a homolog of 2, was also prepared.
Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides
Ong, Derek Yiren,Yen, Zhihao,Yoshii, Asami,Revillo Imbernon, Julia,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 4992 - 4997 (2019/03/13)
New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.
Synthetic method for dihydrostilbenes and anti-inflammatory compounds containing thereof
-
, (2018/05/03)
The present invention aims to provide an effective anti-inflammatory agent without side effects. The present inventors have invented a method for efficiently synthesizing dihydrostilbene and derivatives (compounds 1 to 5) from starting materials at a high yield. In addition, the anti-inflammatory effects were evaluated in LPS-induced RAW-264.7 macrophages. The compounds of dihydrostilbene do not exhibit cytotoxicity and are shown to weakly or well inhibit nitric oxide production induced by LPS at the concentration of 10 andmu;M.COPYRIGHT KIPO 2018
Simple Synthesis of Phytochemicals by Heterogeneous Pd- and Ir-Catalyzed Hydrogen-Borrowing C–C Bond Formation
Hori, Yoji,Suruga, Chiharu,Akabayashi, Yuta,Ishikawa, Tomoka,Saito, Marina,Myoda, Takao,Toeda, Kazuki,Maeda, Yuna,Yoshida, Yutaka
, p. 7295 - 7299 (2018/01/02)
Chitin-supported palladium and iridium catalysts (i.e., Pd/chitin, Ir/chitin) successfully promote the hydrogen borrowing C–C bond formation reaction to afford phytochemicals and aroma compounds in excellent yields.
Dihydrostilbenes and diarylpropanes: Synthesis and in vitro pharmacological evaluation as potent nitric oxide production inhibition agents
Jang, Ha Young,Park, Hyeong Jin,Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
, p. 5438 - 5443 (2016/11/09)
An efficient synthesis of dihydrostilbenes (1–5) and diarylpropanes (6–10) is achieved from the commercially available starting materials and Wittig-Horner reaction, Claisen–Schmidt condensation and hydrogenation as key steps. Later, their nitric oxide (NO) production inhibition effects were evaluated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages as an indicator of anti-inflammatory activity. All the tested compounds significantly decreased NO production in a concentration-dependent manner except compounds 2, 6 and 8 and did not show notable cytotoxicity except compound 1. Two compounds i.e., compound 9 (hindsiipropane B) (100%; IC50?=?1.84?μM) possessed the most potent NO inhibitory activity which was even stronger than the positive control, L-NMMA (90.1%; IC50?=?2.73?μM) followed by compound 4 (75.5%; IC50?=?2.98?μM) at 10?μM concentration and this finding was also further correlated by suppressed expression of LPS stimulated inducible NO synthase. Our study revealed that compound 9, a 1,3-diarylpropane scaffold with 3″,4″-dimethoxyphenyl and 3′,4′-dihydroxy-2′-methoxyphenyl motifs could be considered as potential compound or lead compound for further development of NO production-targeted anti-inflammatory agents.
