705-76-0Relevant articles and documents
Synthesis of [6,6,m]-Tricyclic Compounds via [4+2] Cycloaddition with Au or Cu Catalyst
Kang, Juyeon,Ham, Seunghwan,Seong, Chaehyeon,Oh, Chang Ho
, p. 1039 - 1043 (2021/05/05)
We synthesized [6,6,6]- and [6,6,7]-tricyclic compounds via intramolecular [4+2] cycloaddition by gold or copper catalysts. Substrates for cyclization were prepared by coupling reactions between eight types of diyne and four types of aromatic moieties. We have successfully synthesized eleven tricyclic compounds.
Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction
Sunnapu, Ranganayakulu,Banoth, Saikumar Naik,Reyno,Thomas, Aleena,Venugopal, Navyasree,Rajendar, Goreti
, p. 4103 - 4113 (2020/03/05)
The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.
4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent
Kobayashi, Shoji,Tamura, Tomoki,Yoshimoto, Saki,Kawakami, Takashi,Masuyama, Araki
, p. 3921 - 3937 (2019/11/11)
4-Methyltetrahydropyran (4-MeTHP) is a hydrophobic cyclic ether with potential for industrial applications. We herein report, for the first time, a comprehensive study on the performance of 4-MeTHP as an organic reaction solvent. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen-metal exchange, reduction, oxidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This breadth suggests 4-MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However, 4-MeTHP was found incompatible with strong Lewis acids, and the C?O bond was readily cleaved by treatment with BBr3. Moreover, the radical-based degradation pathways of 4-MeTHP, THP and 2-MeTHF were elucidated on the basis of GC-MS analyses. The data reported herein is anticipated to be useful for a broad range of synthetic chemists, especially industrial process chemists, when selecting the reaction solvent with green chemistry perspectives.
Studies toward the synthesis of caramboxin analogues
Oliveira Filho, Ronaldo E.,Higa, Vanessa M.,Omori, álvaro T.
, p. 528 - 540 (2019/08/26)
Intrigued by the recent discovery of caramboxin by Brazilian researchers, we present the results from our studies toward the racemic synthesis of caramboxin analogs through the ortho-carboxylation of 3,5-dimethoxy benzyl derivatives. Three different approaches were tested, and the route involving a Vilsmeier-Haack formylation followed by a Lindgren oxidation provide a potential intermediate for the synthesis of several caramboxin analogs.
Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-κB/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase
Ho?ek, Jan,Leláková, Veronika,Bobál, Pavel,Pí?ová, Hana,Gazdová, Markéta,Malaník, Milan,Jakubczyk, Karolina,Vesely, Ond?ej,Landa, P?emysl,Temml, Veronika,Schuster, Daniela,Prachyawarakorn, Vilailak,Pailee, Phanruethai,Ren, Gang,Zpurny, Filip,Oravec, Michal,?mejkal, Karel
, p. 1839 - 1848 (2019/08/20)
Stilbenoids are important components of foods (e.g., peanuts, grapes, various edible berries), beverages (wine, white tea), and medicinal plants. Many publications have described the anti-inflammatory potential of stilbenoids, including the widely known trans-resveratrol and its analogues. However, comparatively little information is available regarding the activity of their prenylated derivatives. One new prenylated stilbenoid (2) was isolated from Artocarpus altilis and characterized structurally based on 1D and 2D NMR analysis and HRMS. Three other prenylated stilbenoids were prepared synthetically (9-11). Their antiphlogistic potential was determined by testing them together with known natural prenylated stilbenoids from Macaranga siamensis and Artocarpus heterophyllus in both cell-free and cell assays. The inhibition of 5-lipoxygenase (5-LOX) was also shown by simulated molecular docking for the most active stilbenoids in order to elucidate the mode of interaction between these compounds and the enzyme. Their effects on the pro-inflammatory nuclear factor-κB (NF-κB) and the activator protein 1 (AP-1) signaling pathway were also analyzed. The THP1-XBlue-MD2-CD14 cell line was used as a model for determining their anti-inflammatory potential, and lipopolysaccharide (LPS) stimulation of Toll-like receptor 4 induced a signaling cascade leading to the activation of NF-κB/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) was further evaluated using LPS-stimulated THP-1 macrophages.
Parallel in vitro and in silico investigations into anti-inflammatory effects of non-prenylated stilbenoids
Leláková, Veronika,?mejkal, Karel,Jakubczyk, Karolina,Vesely, Ond?ej,Landa, P?emysl,Václavík, Ji?í,Bobá?, Pavel,Pí?ová, Hana,Temml, Veronika,Steinacher, Theresa,Schuster, Daniela,Granica, Sebastian,Hanáková, Zuzana,Ho?ek, Jan
, p. 431 - 440 (2019/02/19)
Stilbenoids represent a large group of bioactive compounds, which occur in food and medicinal plants. Twenty-five stilbenoids were screened in vitro for their ability to inhibit COX-1, COX-2 and 5-LOX. Piceatannol and pinostilbene showed activity comparable to the zileuton and ibuprofen, respectively. The anti-inflammatory potential of stilbenoids was further evaluated using THP-1 human monocytic leukemia cell line. Tests of the cytotoxicity on the THP-1 and HCT116 cell lines showed very low toxic effects. The tested stilbenoids were evaluated for their ability to attenuate the LPS-stimulated activation of NF-κB/AP-1. Most of the tested substances reduced the activity of NF-κB/AP-1 and later attenuated the expression of TNF-α. The effects of selected stilbenoids were further investigated on inflammatory signaling pathways. Non-prenylated stilbenoids regulated attenuation of NF-?B/AP-1 activity upstream by inhibiting the phosphorylation of MAPKs. A docking study used to in silico analyze the tested compounds confirmed their interaction with NF-?B, COX-2 and 5-LOX.
Methanol as hydrogen source: Transfer hydrogenation of aromatic aldehydes with a rhodacycle
Aboo, Ahmed H.,Bennett, Elliot L.,Deeprose, Mark,Robertson, Craig M.,Iggo, Jonathan A.,Xiao, Jianliang
supporting information, p. 11805 - 11808 (2018/11/10)
A cyclometalated rhodium complex has been shown to perform highly selective and efficient reduction of aldehydes, deriving the hydrogen from methanol. With methanol as both the solvent and hydrogen donor under mild conditions and an open atmosphere, a wide range of aromatic aldehydes were reduced to the corresponding alcohols, without affecting other functional groups.
Discovery of boron-containing compounds as Aβ aggregation inhibitors and antioxidants for the treatment of Alzheimer's disease
Lu, Chuan-Jun,Hu, Jinhui,Wang, Zechen,Xie, Shishun,Pan, Tingting,Huang, Ling,Li, Xingshu
, p. 1862 - 1870 (2018/11/24)
A novel series of boron-containing compounds were designed, synthesized and evaluated as multi-target-directed ligands against Alzheimer's disease. The biological activity results demonstrated that these compounds possessed a significant ability to inhibit self-induced Aβ aggregation (20.5-82.8%, 20 μM) and to act as potential antioxidants (oxygen radical absorbance capacity assay using fluorescein (ORAC-FL) values of 2.70-5.87). In particular, compound 17h is a potential lead compound for AD therapy (IC50 = 3.41 μM for self-induced Aβ aggregation; ORAC-FL value = 4.55). Compound 17h also functions as a metal chelator. These results indicated that boron-containing compounds could be new structural scaffolds for the treatment of AD.
Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents
Semenova, Marina N.,Demchuk, Dmitry V.,Tsyganov, Dmitry V.,Chernysheva, Natalia B.,Samet, Alexander V.,Silyanova, Eugenia A.,Kislyi, Victor P.,Maksimenko, Anna S.,Varakutin, Alexander E.,Konyushkin, Leonid D.,Raihstat, Mikhail M.,Kiselyov, Alex S.,Semenov, Victor V.
, p. 700 - 721 (2019/01/03)
A series of both novel and reported combretastatin analogues, including diarylpyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles, were synthesized via improved protocols to evaluate their antimitotic antitubulin activity using in vivo sea urchin embryo assay and a panel of human cancer cells. A systematic comparative structure-activity relationship studies of these compounds were conducted. Pyrazoles 1i and 1p, isoxazole 3a, and triazole 7b were found to be the most potent antimitotics across all tested compounds causing cleavage alteration of the sea urchin embryo at 1, 0.25, 1, and 0.5 nM, respectively. These agents exhibited comparable cytotoxicity against human cancer cells. Structure-activity relationship studies revealed that compounds substituted with 3,4,5-trimethoxyphenyl ring A and 4-methoxyphenyl ring B displayed the highest activity. 3-Hydroxy group in the ring B was essential for the antiproliferative activity in the diarylisoxazole series, whereas it was not required for potency of diarylpyrazoles. Isoxazoles 3 with 3,4,5-trimethoxy-substituted ring A and 3-hydroxy-4-methoxy-substituted ring B were more active than the respective pyrazoles 1. Of the azoles substituted with the same set of other aryl pharmacophores, diarylpyrazoles 1, 4,5-diarylisoxazoles 3, and 4,5-diaryl-1,2,3-triazoles 7 displayed similar strongest antimitotic antitubulin effect followed by 3,4-diarylisoxazoles 5, 1,5-diaryl-1,2,3-triazoles 8, and pyrroles 10 that showed the lowest activity. Introduction of the amino group into the heterocyclic core decreased the antimitotic antitubulin effect of pyrazoles, triazoles, and to a lesser degree of 4,5-diarylisoxazoles, whereas potency of the respective 3,4-diarylisoxazoles was increased.
A facile, efficient and chemoseletive deprotection of silyl ethers using zinc (II) trifluoromethanesulfonate
Reddy, Kotthireddy Thirumal,Sreenivasulu, Reddymasu,Veronica, Deekala,Chandrasekhar, Choragudi,Anitha, Kowthalam,Raju, Rudraraju Ramesh
, p. 191 - 195 (2018/03/09)
Background: A number of protective groups for hydroxyl functional groups have been developed to date. Alcohols are most commonly protected as ethers and esters, where in alkyl and benzyl ethers are strong protective groups while others, like THP, TBS, TPS and MEM/MOM ethers are acid labile. Among all other hydroxyl protecting groups, Silyl ethers are the most frequently used protecting groups because they are easily and efficiently installed and are stable to a variety of useful reagents and reaction conditions. Among the silyl ethers, triethylsilyl (TES), tert-butyldimethylsilyl (TBDMS), triisopropylsilyl (TIPS), and tert-butyldiphenylsilyl (TBDPS) moieties are the frequently used hydroxyl protecting groups in multi step organic syntheses. Methods: A mild, efficient and selective method for the deprotection of variety of silyl ethers developed in high yields by using 20 mol % of Zinc (II) trifluoromethanesulfonate (Zn(OTf)2) at room temperature in methanol as a solvent without affecting both the acid and base sensitive protecting groups was reported. Results: To study the generality of this methodology, several silyl ethers were prepared from a variety of substrates having different protecting groups and subjected to desilylation using Zn(OTf)2 in MeOH. Conclusion: In conclusion, mild and efficient protocols for the deprotection of variety of silyl ethers using 20 mol % of Zn(OTf)2 at room temperature in MeOH have been established, in which both the acid and base sensitive groups are unaffected.
