6554-98-9Relevant academic research and scientific papers
Fluorinated N, N -dialkylaminostilbenes for wnt pathway inhibition and colon cancer repression
Zhang, Wen,Sviripa, Vitaliy,Kril, Liliia M.,Chen, Xi,Yu, Tianxin,Shi, Jiandang,Rychahou, Piotr,Evers, B. Mark,Watt, David S.,Liu, Chunming
, p. 1288 - 1297 (2011)
Colorectal cancer (CRC) is the second leading cause of cancer-related mortality in the USA. CRC is initiated by mutations of the tumor suppressor gene, adenomatous polyposis coli (APC), or β-catenin gene. These mutations stabilize β-catenin and constitutively activate Wnt/β-catenin target genes, such as c-Myc and cyclin D1, ultimately leading to cancer. Naturally occurring stilbene derivatives, resveratrol and pterostilbene, inhibit Wnt signaling and repress CRC cell proliferation but are ineffective at concentrations less than 10 μM. To understand the structure-activity relationship within these stilbene derivatives and to develop more efficacious Wnt inhibitors than these natural products, we synthesized and evaluated a panel of fluorinated N,N-dialkylaminostilbenes. Among this panel, (E)-4-(2,6-difluorostyryl)-N,N-dimethylaniline (4r) inhibits Wnt signaling at nanomolar levels and inhibits the growth of human CRC cell xenografts in athymic nude mice at a dosage of 20 mg/kg. These fluorinated N,N-dialkylaminostilbenes appear to inhibit Wnt signaling downstream of β-catenin, probably at the transcriptional level.
Bimetallic Ni–Pd Synergism—Mixed Metal Catalysis of the Mizoroki-Heck Reaction and the Suzuki–Miyaura Coupling of Aryl Bromides
Kashid, Abhijit A.,Patil, Dharmaraj J.,Mali, Ramling D.,Patil, Vijay P.,Neethu,Meroliya, Heena K.,Waghmode, Shobha A.,Iyer, Suresh
, p. 353 - 358 (2020/08/05)
Abstract: A combination of Pd and Ni complexes activated aryl bromides for the thermal Mizoroki-Heck reaction and Suzuki coupling giving high yields in short reaction times. A thermal redox mechanism probably occurs whereby Ni complex transfers electron and reduces the Pd (II) to Pd (0) which then takes the reactants through the standard protocol of oxidative-addition, migratory insertion and reductive elimination, typical for the Mizoroki-Heck reaction and the Suzuki coupling. Graphic Abstract: [Figure not available: see fulltext.]
Palladium-Based Catalysts Supported by Unsymmetrical XYC–1 Type Pincer Ligands: C5 Arylation of Imidazoles and Synthesis of Octinoxate Utilizing the Mizoroki–Heck Reaction
Maji, Ankur,Singh, Ovender,Singh, Sain,Mohanty, Aurobinda,Maji, Pradip K.,Ghosh, Kaushik
, p. 1596 - 1611 (2020/04/29)
A series of new unsymmetrical (XYC–1 type) palladacycles (C1–C4) were designed and synthesized with simple anchoring ligands L1–4H (L1H = 2-((2-(4-methoxybenzylidene)-1-phenylhydrazinyl)methyl)pyridine, L2H = N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono)methyl)aniline, L3H = N,N-diethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono)methyl) aniline and L4H = 4-(4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono) methyl)phenyl)morpholine H = dissociable proton). Molecular structure of catalysts (C1–C4) were further established by single X-ray crystallographic studies. The catalytic performance of palladacycles (C1–C4) was explored with the direct Csp2–H arylation of imidazoles with aryl halide derivatives. These palladacycles were also applied for investigating of Mizoroki–Heck reactions with aryl halides and acrylate derivatives. During catalytic cycle in situ generated Pd(0) nanoparticles were characterized by XPS, SEM and TEM analysis and possible reaction pathways were proposed. The catalyst was employed as a pre-catalyst for the gram-scale synthesis of octinoxate, which is utilized as a UV-B sunscreen agent.
Chemoselective acid-catalyzed [4 + 2]-cycloaddition reactions of: Ortho -quinone methides and styrenes/stilbenes/cinnamates
Akkarasereenon, Kornkamon,Ploypradith, Poonsakdi,Ruchirawat, Somsak,Tangdenpaisal, Kassrin
supporting information, p. 8854 - 8866 (2020/11/23)
ortho-Quinone methides (o-QMs) generated from the corresponding benzyl acetate precursors chemoselectively underwent the formal [4 + 2]-cycloadditions with the olefin of styrene, stilbene, or cinnamate derivatives by using different transition metal salts or Br?nsted acids. Such selectivity was obtained when these olefins either separately acted as the dienophiles or were simultaneously present on the same dienophiles. Complete selectivity was also achieved between the stilbene olefin and acetylene to furnish the key chroman intermediate for the subsequent ring-closing metathesis (RCM), affording the corresponding tetracyclic 5H-dihydronaphtho[1,2-c]chromene. This journal is
Self-Assembled Multilayer Iron(0) Nanoparticle Catalyst for Ligand-Free Carbon-Carbon/Carbon-Nitrogen Bond-Forming Reactions
Akiyama, Toshiki,Arisawa, Mitsuhiro,Haneoka, Hitoshi,Harada, Kazuo,Hasegawa, Jun-Ya,Honma, Tetsuo,Mashima, Kazushi,Sato, Yoshihiro,Shimoda, Shuhei,Shio, Yasunori,Suzuki, Takeyuki,Tamenori, Yusuke,Tsurugi, Hayato,Tsuruta, Kazuki,Wada, Yuki,Yamada, Makito
supporting information, p. 7244 - 7249 (2020/10/12)
Self-assembled multilayer iron(0) nanoparticles (NPs, 6-10 nm), namely, sulfur-modified Au-supported Fe(0) [SAFe(0)], were developed for ligand-free one-pot carbon-carbon/carbon-nitrogen bond-forming reactions. SAFe(0) was successfully prepared using a well-established metal-nanoparticle catalyst preparative protocol by simultaneous in situ metal NP and nanospace organization (PSSO) with 1,4-bis(trimethylsilyl)-1,4-dihydropyrazine (Si-DHP) as a strong reducing agent. SAFe(0) was easy to handle in air and could be recycled with a low iron-leaching rate in reaction cycles.
A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation
Thiel, Niklas O.,Kaewmee, Benyapa,Tran Ngoc, Trung,Teichert, Johannes F.
, p. 1597 - 1603 (2020/02/05)
Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom-economic reducing agent dihydrogen (H2), only few catalysts for the challenging E-selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E-selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E-alkenes employing H2, which could serve as a general method for synthesis.
Convenient and efficient Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions catalyzed by 1,3,4-trisubstituted-1,2,3-triazolium iodide and palladium salt systems
Shahini,Achar, Gautam,Budagumpi, Srinivasa,Dateer, Ramesh B.,Müller-Bunz, Helge,Tacke, Matthias,Patil, Siddappa A.
, p. 528 - 549 (2019/02/26)
A series of 1,3,4-trisubstituted-1,2,3-triazolium iodide salts (4a–c) were synthesized via a three-step reaction sequence. Corresponding anilines (1a–c) were converted to azides (2a–c) which were then treated with phenylacetylene with “Click” chemistry to access 1,4-disubstituted-1,2,3-triazoles (3a–c). Subsequent methylation of 1,4-disubstituted-1,2,3-triazoles (3a–c) yielded 1,3,4-trisubstituted-1,2,3-triazoliumiodide salts (4a–c) in appreciable yields. All the synthesized compounds were characterized by 1H and 13C NMR, ATR–IR spectroscopic techniques and elemental analyses. Additionally, the structure of 1-(4-chlorophenyl)-4-phenyl-1,2,3-triazole (3b) was confirmed by single crystal X-ray diffraction analysis. The catalytic activity of 4a–c in a catalytic system consisting of 1,3,4-trisubstituted-1,2,3-triazoliumiodide salt/palladium(II) acetate/base were investigated toward Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions. The Suzuki–Miyaura cross-coupling reactions were carried out under mild reaction conditions with good to excellent yields, whereas Heck–Mizoroki cross-coupling reactions were performed at elevated temperature with moderate yields. Further, in situ method skips the synthetic procedure of preparing the palladium(II) complexes and hence is more economical and less tedious. (Figure presented.).
Cobalt catalyzed stereodivergent semi-hydrogenation of alkynes using H2O as the hydrogen source
Li, Kangkui,Khan, Ruhima,Zhang, Xuexin,Gao, Yang,Zhou, Yongyun,Tan, Heng,Chen, Jingchao,Fan, Baomin
supporting information, p. 5663 - 5666 (2019/05/21)
Cobalt-catalyzed stereodivergent semi-hydrogenation of internal alkynes to alkenes is developed. The reaction proceeded through transfer hydrogenation under mild conditions using a base metal CoI2 as the catalyst, and H2O/MeOH as the hydrogen source with Zn as the reductant. The E/Z-selectivity of the product could be switched by changing the solvent and by inclusion/exclusion of a bidentate phosphine ligand (dppe). This method provides a simple and cost effective pathway for the synthesis of 1,2-dideuterioalkenes.
Galloyl esters of trans-stilbenes are inhibitors of FASN with anticancer activity on non-small cell lung cancer cells
Tan, Yu-Jia,Ali,Tee, Sheng-Yang,Teo, Jun-Ting,Xi, Yu,Go, Mei-Lin,Lam
, (2019/08/20)
Fatty acid synthase (FASN) is a lipogenic enzyme that is selectively upregulated in malignant cells. There is growing consensus on the oncogenicity of FASN-driven lipogenesis and the potential of FASN as a druggable target in cancer. Here, we report the synthesis and FASN inhibitory activities of two novel galloyl esters of trans-stilbene EC1 and EC5. Inhibition of FASN was accompanied by a loss in AKT activation and profound apoptosis in several non-small cell lung cancer (NSCLC) cells at the growth inhibitory concentrations of EC1 and EC5. Both FASN and phospho-AKT levels were concurrently downregulated. However, addition of a lipid concentrate to the treated cells reinstated cell viability and reversed the loss of FASN and AKT protein levels, thus recapitulating the causal relationship between FASN inhibition and the loss in cell viability.
Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage
Peng, Yi,Fan, Yan-Hui,Li, Si-Yuan,Li, Bin,Xue, Jing,Deng, Qing-Hai
supporting information, p. 8389 - 8394 (2019/10/16)
C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.
