4282-49-9Relevant academic research and scientific papers
Quantifying Through-Space Substituent Effects
Adam, Catherine,Burns, Rebecca J.,Cockroft, Scott L.,Mati, Ioulia K.,Muchowska, Kamila B.
supporting information, p. 16717 - 16724 (2020/07/24)
The description of substituents as electron donating or withdrawing leads to a perceived dominance of through-bond influences. The situation is compounded by the challenge of separating through-bond and through-space contributions. Here, we probe the experimental significance of through-space substituent effects in molecular interactions and reaction kinetics. Conformational equilibrium constants were transposed onto the Hammett substituent constant scale revealing dominant through-space substituent effects that cannot be described in classic terms. For example, NO2 groups positioned over a biaryl bond exhibited similar influences as resonant electron donors. Meanwhile, the electro-enhancing influence of OMe/OH groups could be switched off or inverted by conformational twisting. 267 conformational equilibrium constants measured across eleven solvents were found to be better predictors of reaction kinetics than calculated electrostatic potentials, suggesting utility in other contexts and for benchmarking theoretical solvation models.
N-Sulfonyl-aminobiaryls as Antitubulin Agents and Inhibitors of Signal Transducers and Activators of Transcription 3 (STAT3) Signaling
Lai, Mei-Jung,Lee, Hsueh-Yun,Chuang, Hsun-Yueh,Chang, Li-Hsun,Tsai, An-Chi,Chen, Mei-Chuan,Huang, Han-Lin,Wu, Yi-Wen,Teng, Che-Ming,Pan, Shiow-Lin,Liu, Yi-Min,Mehndiratta, Samir,Liou, Jing-Ping
, p. 6549 - 6558 (2015/09/07)
A series of N-sulfonyl-aminobiaryl derivatives have been examined as novel antitubulin agents. Compound 21 [N-(4′-cyano-3′-fluoro-biphenyl-2-yl)-4-methoxy-benzenesulfonamide] exhibits remarkable antiproliferative activity against four cancer cell lines (pancreatic AsPC-1, lung A549, liver Hep3B, and prostate PC-3) with a mean GI50 value of 57.5 nM. Additional assays reveal that 21 inhibits not only tubulin polymerization but also the phosphorylation of STAT3 inhibition with an IC50 value of 0.2 μM. Four additional compounds (8, 10, 19, and 35) are also able to inhibit this phosphorylation. This study describes novel N-sulfonyl-aminobiaryl (biaryl-benzenesulfonamides) as potent anticancer agents targeting both STAT3 and tubulin. (Chemical Equation Presented).
Microwave-enhanced cadogan cyclization: An easy access to the 2-substituted carbazoles and other fused heterocyclic systems
Appukkuttan, Prasad,Van Der Eycken, Erik,Dehaen, Wim
, p. 127 - 133 (2007/10/03)
A microwave-enhanced Suzuki-Miyaura cross-coupling reaction in combination with a microwave-assisted Cadogan reductive cyclization is presented as an easy access to a variety of 2-substituted carbazoles and other fused heterocyclic systems. Microwave irradiation was found very useful in minimizing the proto-deboronation issues in the cross-coupling reaction, and enhances the rate of reductive cyclization in a dramatic manner.
Substituted piperidines and methods of use
-
Page 35, (2010/02/05)
Selected substituted piperidine compounds are effective for prophylaxis and treatment of diseases, such as obesity and the like. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving activation of the melanocortin receptor. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.
Potassium peroxodisulfate: A convenient oxidizing agent for aromatization of 1,4-dihydropyridines
Memarian,Mohammadpoor-Baltork,Sadeghi,Samani
, p. 727 - 728 (2007/10/03)
A series of 13 different 4-substituted 2,6-dimethyl-3,5-diethoxycarbonyl)-1,4-dihydropyridines have been oxidized to pyridine derivatives by potassium peroxodisulfate in dry and wet acetonitrile solution at reflux condition. Formation of two kinds of products has been observed depending on the type of 4-substituent. Addition of water affects only the rate of oxidation.
Stille and suzuki cross coupling reactions of o-nitrophenyl triflates: A versatile route to a variety of heterocycles
Holzapfel, Cedric W.,Dwyer, Catherine
, p. 1513 - 1518 (2007/10/03)
The cross coupling reactions of selected o-nitrophenyl triflates with arylstannane and arylboron substrates are reported. The resultant 2-nitrobiphenyls provide ready access to a variety of substituted heterocycles.
Some coordination chemistry of the bidentate nitrogen-donor ligand 2-(2-aminophenyl)pyridine
Cargill Thompson, Alexander M.W.,Batten, Stuart R.,Jeffery, John C.,Rees, Leigh H.,Ward, Michael D.
, p. 109 - 114 (2007/10/03)
Complexes of the chelating bidentate nitrogen-donor ligand 2-(2-aminophenyl)pyridine (L) are described. [PdL2] [PF6]2 (1) forms two types of crystal (1a,b) of which (1a) was crystallographically characterized [space group
A simple and efficient synthesis of 2,- 3-, or 4-(2-nitrophenyl)pyridine derivatives via palladium catalyzed ullmann cross-coupling reaction
Shimizu, Noboru,Kitamura, Takahiro,Watanabe, Koichiro,Yamaguchi, Takashi,Shigyo, Hiromichi,Ohta, Tomio
, p. 3421 - 3424 (2007/10/02)
The Ullmann cross-coupling reaction of halopyridines with 2-bromonitirobenzenes was successffully catalyzed by low valent palladium [Pd(PPh3)4, PdCl2(PPh3)2, PdCl2] to afford (2-nitrophenyl)pyridine derivatives in good to excellent yield.
