101601-80-3Relevant articles and documents
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.
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.
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.
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.
