101601-80-3Relevant academic research and scientific papers
Halogen-Bond-Promoted Photoactivation of Perfluoroalkyl Iodides: A Photochemical Protocol for Perfluoroalkylation Reactions
Wang, Yaxin,Wang, Junhua,Li, Guo-Xing,He, Gang,Chen, Gong
, p. 1442 - 1445 (2017)
A new protocol for photochemical perfluoroalkylation reactions using perfluoroalkyl iodide, amine additive, and THF solvent is reported. This protocol does not require a photoredox catalyst and proceeds at ambient temperature with irradiation from a compact fluorescent lamp, low-intensity UV lamp, or sunlight. This protocol can be applied to the synthesis of perfluoroalkyl-substituted phenanthridines as well as effect the iodo-perfluoroalkylation of alkenes/alkynes and the C-H perfluoroalkylation of electron-rich arenes and heteroarenes. This C-H perfluoroalkylation reaction offers a unique method for site-selective labeling of oligopeptides at the tryptophan residue.
Preparation of unsymmetrical biaryls via Ni- or Pd-catalyzed coupling of aryl chlorides with arylzincs
Miller, Joseph A.,Farrell, Robert P.
, p. 6441 - 6444 (1998)
Unsymmetrical biaryls may be prepared in an efficient manner using aryl chlorides as substrates in Negishi-type cross-coupling reactions with arylzinc reagents via either Ni- or Pd-catalysis. Since a wide range of functional groups (e.g., nitrile, carbonyl, ester) tolerate arylzinc compounds, this methodology allows for the direct synthesis of biaryls from aryl chlorides possessing these moieties.
An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine
Caron, Stephane,Massett, Steve S.,Bogle, David E.,Castaldi, Michael J.,Braish, Tamim F.
, p. 254 - 256 (2001)
The synthesis of 2-phenyl-3-aminopyridine, a key intermediate in the preparation of 2-phenyl-3-aminopiperidine, from 2-chloro-3-aminopyridine is described using an imine as a protecting group for an aminopyridine. The in situ protection of 2-chloro-3-amin
Asymmetric hydrogenation of 2-aryl-3-phthalimidopyridinium salts: Synthesis of piperidine derivatives with two contiguous stereocenters
Zhang, Xumu,Chen, Gen-Qiang,Zheng, Long-Sheng,Wang, Fangyuan,Ye, Xiang-Yu
, p. 8882 - 8887 (2020)
Asymmetric hydrogenation of 2-aryl-3-phthalimido-pyridinium salts catalyzed by the Ir/SegPhos catalytic system was described, leading to the corresponding chiral piperidine derivatives bearing two contiguous chiral centers, with high levels of enantioselectivities and diastereoselectivities. A gram-scale experiment has demonstrated the utility of this approach. The phthaloyl group could be easily removed and then smoothly converted to key intermediate (+)-CP-99994 as one of the neurokinin 1 receptor antagonists.
A palladium complex confined in a thiadiazole-functionalized porous conjugated polymer for the Suzuki-Miyaura coupling reaction
Qian, Yingjie,Jeong, Sang Yung,Baeck, Sung-Hyeon,Jin, Myung-Jong,Shim, Sang Eun
, p. 33563 - 33571 (2019)
Porous organic polymers (POPs) with well-distributed and tunable functional groups acting as ligands for specific reactions are promising supports for confining useful novel metals such as Pd, Au, and Pd. Herein, a thiadiazole-containing POP has been successfully synthesized and used for immobilizing Pd species. Pd immobilized inside the micropores (2.3 nm) of the POP material is easily prepared owing to a large amount of the strong anchoring group, thiadiazole, which is intrinsically distributed in the as-prepared POP. The rigid thiadiazole-containing polymer can stabilize the central metal rather than poisoning it. The as-prepared catalyst shows excellent catalytic activity in Suzuki-Miyaura coupling reactions under mild reaction conditions and low catalyst loading. Importantly, the intrinsically distributed thiadiazole ligands can stabilize the Pd moiety, preventing aggregation and leaching, and afford excellent catalytic lifetimes. Consequently, the catalyst can be reused 10 times without a significant loss of its catalytic activity.
Direct synthesis of hetero-biaryl compounds containing an unprotected NH2 group via Suzuki-Miyaura reaction
Itoh, Takahiro,Mase, Toshiaki
, p. 3573 - 3577 (2005)
Hetero-biaryl compounds were prepared via the Suzuki-Miyaura coupling reaction of hetero-aryl moieties containing an unprotected NH2 group and arylboronic acids. D-t-BPF was found to be an efficient ligand for the cross-coupling of NH2/su
Discovery of novel 2-aryl-3-sulfonamido-pyridines (HoAns) as microtubule polymerization inhibitors with potent antitumor activities
Zhu, Heping,Ying, Shilong,Zhou, Bingluo,Liang, Xiao,He, Quan,Song, Ping,Hu, Xinyang,Shi, Keqiang,Xiong, Mingteng,Jin, Hongchuan,Pan, Yuanjiang
, (2020/12/29)
Microtubules play a vital role in cell mitosis. Drugs targeting taxol or vinca binding site of tubulin have been proved an effective way to against cancer. However, drug resistance and cancer recurrence are inevitable, there is an urgent need to search for new microtubule-targeting agents (MTAs). In our study, a series of novel 2-aryl-3-sulfonamido-pyridines (HoAns) had been designed, synthesized, and evaluated for their antiproliferative activities in vitro and in vivo. Among them, compound HoAn32 exhibited the most potent activity with IC50 values ranging from 0.170 to 1.193 μM in a panel of cancer cell lines. Mechanism studies indicated that compound HoAn32 bound to the colchicine site of β-tubulin, resulting in colony formation inhibition, G2/M phase cell cycle arrest, cell apoptosis as well as increased the generation of ROS in both RKO and SW620 cells. In addition, compound HoAn32 showed potent anti-vascular activity in vitro. Furthermore, compound HoAn32 also exhibited outstanding antitumor activity in SW620 xenograft tumor models without observable toxic effects, which was more potent than that of ABT-751. In conclusion, our findings suggest that compound HoAn32 may be a promising microtubule destabilizing agent and deserves for further development in cancer therapy.
Pyridine-2-aryl-3-sulfonamide compound as well as synthesis method and application thereof
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Paragraph 0036; 0037; 0122; 0123, (2020/07/13)
The invention discloses a pyridine-2-aryl-3-sulfonamide compound as well as a synthesis method and application thereof in preparation of an antitumor drug or tubulin polymerization inhibitor. The pyridine-2-aryl-3-sulfonamide compound has a structural general formula (I), X, Y and Z are selected from C or N atoms, and R1 represents a monosubstituted or polysubstituted group; r2 represents a monosubstituted or polysubstituted group; and R3 represents hydrogen or a different C1-5 alkoxy-substituted benzenesulfonyl group. The invention discloses application of pyridine-2-aryl-3-sulfonamide compounds in preparation of medicines. The pyridine-2-aryl-3-sulfonamide compounds are used as active ingredients for preparing antitumor medicines or tubulin polymerization inhibitors. The antitumor drugsare drugs for resisting colon cancer, breast cancer, liver cancer, lung cancer, stomach cancer or pancreatic cancer.
Pd-Catalyzed Suzuki coupling reactions of aryl halides containing basic nitrogen centers with arylboronic acids in water in the absence of added base
Li, Zhao,Gelbaum, Carol,Campbell, Zachary S.,Gould, Paul C.,Fisk, Jason S.,Holden, Bruce,Jaganathan, Arvind,Whiteker, Gregory T.,Pollet, Pamela,Liotta, Charles L.
supporting information, p. 15420 - 15432 (2017/12/15)
The Pd-catalyzed Suzuki coupling reactions of a series of aryl chlorides and aryl bromides containing basic nitrogen centers with arylboronic acids in water in the absence of added base are reported. The reactions proceed either partially or entirely under acidic conditions. After surveying twenty-two phosphorus ligands, high yields of products were obtained with aryl chlorides only when a bulky ligand, 2-(di-tert-butyl-phosphino)-1-phenyl-1H-pyrrole (cataCXiumPtB) was used. In contrast, aryl bromides produced high yields of products in the absence of both added base and added ligand. In order to explore the Suzuki coupling process entirely under acidic conditions, a series of reactions were conducted in buffered acidic media using several model substrates. 4-Chlorobenzylamine, in the presence of cataCXiumPtB, produced high yields of product at buffered pH 6.0; the yields dropped off precipitously at buffered pH 5.0 and lower. The fall-off in yield was attributed to the decomposition of the Pd-ligand complex due to the protonation of the ligand in the more acidic aqueous media. In contrast, in the absence of an added ligand, 4-amino-2-chloropyridine produced quantitative yields at buffered pH 3.5 and 4.5 while 4-amino-2-bromopyridine produced quantitative yields in a series of buffered media ranging from pH 4.5 to 1.5. These substrates are only partially protonated in acidic media and can behave as active Pd ligands in the Suzuki catalytic cycle.
METHODS FOR EXTERNAL BASE-FREE SUZUKI COUPLINGS
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Paragraph 0035-0036, (2017/07/14)
The present disclosure describes a method of coupling a first aromatic compound to a second aromatic compound, the method comprising: (a) preparing a reaction mixture comprising the first aromatic compound, the second aromatic compound, a catalyst and water; the reaction mixture does not contain an external base, the reaction mixture having an initial pH of from 11 to 1; the catalyst having at least one group 10 atom; the first aromatic compound having a halogen, triflate or sulfonate substituent; the second aromatic compound having a boron-containing substituent; wherein, at least one of the first aromatic compound or the second aromatic compound includes one or more heteroatom; and (b) reacting the first aromatic compound and the second aromatic compound in the reaction mixture, the reaction mixture having a final pH following reaction of the first aromatic compound and the second aromatic compound.
