6380-08-1Relevant articles and documents
A Broad-Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**
Wei, Mingjie,Liang, Dacheng,Cao, Xiaohui,Luo, Wenjun,Ma, Guojian,Liu, Zeyuan,Li, Le
supporting information, p. 7397 - 7404 (2021/02/16)
A broad-spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1-hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for sterically hindered substrates. Catalyst loading is generally low and only 0.02 mol % of catalyst is required for the multidecagram-scale synthesis of an amantadine derivative. In addition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via a key intermediate sulfonyl fluoride 13. Since a large number of amines are commercially available, this route provides a facile entry to access Fedratinib analogues for biological screening.
N-substituted benzenesulfonamide compounds: DNA binding properties and molecular docking studies
Güng?r, Seyit Ali,Tümer, Mehmet,K?se, Muhammet,Erkan, Sultan
, (2021/04/02)
Benzenesulfonamide-based imine compounds 5–8 were prepared and screened for their binding properties to the FSdsDNA. The structures of synthesized compounds were elucidated by the spectroscopic and analytical methods. Compounds 5–8 were screened for their
Method for preparing P-phenylenediamine from aniline
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Paragraph 0075-0126, (2020/07/21)
The invention provides a method for preparing p-phenylenediamine from aniline. The method comprises the following steps: protecting amino on aniline by using p-toluenesulfonyl, mixing the aniline withan amino donor, an oxidant and a catalyst Ru-Cu/TS-1 to carry out ammoniation reaction, and performing separation after deprotection to obtain p-phenylenediamine. According to the invention, a protecting group strategy is adopted to protect amino on aniline by p-toluenesulfonyl, meanwhile, a C-H bond of a benzene ring para-position is induced and activated, and a catalyst Ru-Cu/TS-1 is adopted for catalyzing an ammoniation reaction, so that the ammoniation efficiency and selectivity can be greatly improved, and the yield and purity of p-phenylenediamine are improved. Moreover, the reaction conditions are mild, the selectivity is good, and the method is a green and environment-friendly synthesis route.
Amide derivatives of Gallic acid: Design, synthesis and evaluation of inhibitory activities against in vitro α-synuclein aggregation
Bai, Su-Ping,Chen, Li,Huang, Guo-Long,Lü, Ming-Huan,Xu, Ji,Zhang, Yun-Xiao
supporting information, (2020/06/29)
Gallic acid (GA), a natural phenolic acid, has received numerous attention because of its anti-oxidative, anti-inflammatory, and anti-cancer activity. More importantly, GA can act as an efficient inhibitor of α-Synuclein (α-Syn) aggregation at early stages. Nevertheless, some evidences suggest that GA is unlikely to cross the blood–brain barrier because of its high hydrophilicity. Hence, GA may not be considered as a promising candidate or entering brain and directly affecting the central nervous system. Accordingly, we have designed and synthesized a series of amide derivatives of GA, some of which possess appropriate lipophilicity and hydrophilicity with LogP (2.09–2.79). Meanwhile, these sheet-like conjugated compounds have good π-electron delocalization and high ability of hydrogen-bond formation. Some compounds have shown better in vitro anti-aggregation activities than GA towards α-Syn, with IC50 down to 0.98 μM. The valid modification strategy of GA is considered an efficient way to discover novel inhibitors of α-Syn aggregation.
Design and synthesis of sulfonamide-substituted diphenylpyrimidines (SFA-DPPYs) as potent Bruton's tyrosine kinase (BTK) inhibitors with improved activity toward B-cell lymphoblastic leukemia
Liu, He,Qu, Menghua,Xu, Lina,Han, Xu,Wang, Changyuan,Shu, Xiaohong,Yao, Jihong,Liu, Kexin,Peng, Jinyong,Li, Yanxia,Ma, Xiaodong
, p. 60 - 69 (2017/04/24)
A new series of diphenylpyrimidine derivatives (SFA-DPPYs) were synthesized by introducing a functional sulfonamide into the C-2 aniline moiety of pyrimidine template, and then were biologically evaluated as potent Bruton's tyrosine kinase (BTK) inhibitors. Among these molecules, inhibitors 10c, 10i, 10j and 10k displayed high potency against the BTK enzyme, with IC50 values of 1.18?nM, 0.92?nM, 0.42?nM and 1.05?nM, respectively. In particular, compound 10c could remarkably inhibit the proliferation of the B lymphoma cell lines at concentrations of 6.49?μM (Ramos cells) and 13.2?μM (Raji cells), and was stronger than the novel agent spebrutinib. In addition, the inhibitory potency toward the normal PBMC cells showed that inhibitor 10c possesses low cell cytotoxicity. All these explorations indicated that molecule 10c could serve as a valuable inhibitor for B-cell lymphoblastic leukemia treatment.
Design, synthesis and biological evaluation of sulfonamide-substituted diphenylpyrimidine derivatives (Sul-DPPYs) as potent focal adhesion kinase (FAK) inhibitors with antitumor activity
Qu, Menghua,Liu, Zhihao,Zhao, Dan,Wang, Changyuan,Zhang, Jianbin,Tang, Zeyao,Liu, Kexin,Shu, Xiaohong,Yuan, Hong,Ma, Xiaodong
, p. 3989 - 3996 (2017/07/05)
A class of sulfonamide-substituted diphenylpyrimidines (Sul-DPPYs) were synthesized to improve activity against the focal adhesion kinase (FAK). Most of these new Sul-DPPYs displayed moderate activity against the FAK enzyme with IC50 values of less than 100?nM; regardless, they could effectively inhibit several classes of refractory cancer cell lines with IC50 values of less than 10?μM, including the pancreatic cancer cell lines (AsPC-1, Panc-1 and BxPC-3), the NSCLC-resistant H1975 cell line, and the B lymphocyte cell line (Ramos cells). Results of flow cytometry indicated that inhibitor 7e promoted apoptosis of pancreatic cancer cells in a dose-dependent manner. In addition, it almost completely induced the apoptosis at a concentration of 10?μM. Compound 7e may be selected as a potent FAK inhibitor for the treatment of pancreatic cancer.
Synthesis of Oxindoles through the gold-catalyzed oxidation of N-arylynamides
Yang, Liu-Qing,Wang, Kai-Bing,Li, Chuan-Ying
supporting information, p. 2775 - 2779 (2013/06/27)
α-Oxo gold carbenoids generated by the oxidation of N-arylynamides can be trapped intramolecularly at the ortho position of the aryl ring to give functionalized oxindoles under mild reaction conditions. Pyridine N-oxide works as the oxidant, ligand, and base in this transformation. Copyright
Samarium(0) and 1,1′-dioctyl-4,4′-bipyridinium dibromide: A novel electron-transfer system for the chemoselective reduction of aromatic nitro groups
Yu,Liu,Hu
, p. 919 - 924 (2007/10/03)
A mild and efficient electron-transfer method was developed for the chemoselective reduction of aromatic nitro groups using samarium(0) metal in the presence of a catalytic amount of 1,1′-dioctyl-4,4′-bipyridinium dibromide. This method was found to give the product aromatic amine in 79-99% yield with selectivity over a number of other functional and protecting groups such as alkene, azide, benzyl ether, nitrile, amide, halide, p-toluenesulfonamide, t-Boc, tert-butyldiphenylsilyl ether, and aliphatic nitro groups. Our results also indicate that samarium(0) plays an important role in the reduction process and that 1,1′-dioctyl-4,4′-bipyridinium dibromide acts as an electron-transfer catalyst and is essential in the activation of samarium(0) metal. The major active reducing agent responsible for the reduction is believed to be the radical cation species formed from 1,1′-dioctyl-4,4′-bipyridinium dibromide.
Photolysis of p-Toluenesulfonyl Azide and Its Charge-Transfer Complex with Aniline
Hoyle, C. E.,Lenox, R. S.,Christie, P. A.,Shoemaker, R. A.
, p. 2056 - 2061 (2007/10/02)
Photolysis of p-toluenesulfonyl azide (1) in p-xylene and cyclohexane gives primarily the products derived from insertion of (p-tolylsulfonyl)nitrene into the solvent.For p-xylene, an unstable intermediate product is formed which decomposes in the dark at room temperature to give both the ring-insertion product and the corresponding p-toluenesulfonamide (2).Photolysis of the ground-state charge-transfer complex between p-toluenesulfonyl azide and aniline gives six products, the major product being the sulfonyl hydrazide 7.Furthermore, formation of the insertion product by reaction with the solvent provides evidence for production of (p-tolylsulfonyl)nitrene from the excited charge-transfer complex.
