- PhzA/B catalyzes the formation of the tricycle in phenazine biosynthesis
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Phenazines are redox-active bacterial secondary metabolites that participate in important biological processes such as the generation of toxic reactive oxygen species and the reduction of environmental iron. Their biosynthesis from chorismic acid depends
- Ahuja, Ekta G.,Janning, Petra,Mentel, Matthias,Graebsch, Almut,Breinbauer, Rolf,Hiller, Wolf,Costisella, Burkhard,Thomashow, Linda S.,Mavrodi, Dmitri V.,Blankenfeldt, Wulf
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- Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines
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A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).
- Wolf, Christian,Liu, Shuanglong,Mei, Xuefeng,August, Adam T.,Casimir, Michael D.
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- Ligand-free iron/copper cocatalyzed N-arylations of aryl halides with amines under microwave irradiation
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Ligand-free iron/copper cocatalyzed cross-coupling reactions of aryl halides with amines were carried out to provide the corresponding coupling products in good yields. It is worth noting that the method displays a broad substrate scope, and is convenient, rapid, low-cost and environmentally friendly.
- Guo, Diliang,Huang, He,Zhou, Yu,Xu, Jinyi,Jiang, Hualiang,Chen, Kaixian,Liu, Hong
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- Iridium-Catalyzed Direct C-H Amination with Alkylamines: Facile Oxidative Insertion of Amino Group into Iridacycle
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Described herein is the development of CpIr(III)-catalyzed direct arene C-H amination using alkylamines as an amino source. This C-N bond formation showcases a notable example of cross-dehydrogenative coupling to install an amino functionality at the orth
- Kim, Hyunwoo,Chang, Sukbok
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- Melatonin derivatives combat with inflammation-related cancer by targeting the Main Culprit STAT3
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The combination between two well-studied bioactive compounds melatonin and salicylic acid with proper modifications unexpectedly creates a sharp pair of “scissors” cutting off the vicious connection between inflammation and cancer by targeting a key contributor Signal Transducers and Activators of Transcription 3 (STAT3) in the two pathological processes. A representative compound P-3 with IC50 values on each tested cell line ranging from 7.37 to 18.62 μM among the designed melatonin derivatives is equipped with the ability of curbing inflammation-promoting cancer by down-regulating the expression, activation and nuclear translocation of STAT3, breaking the feedforward loop of STAT3 activation by decreasing the expression of pro-tumorigenic cytokines, and inducing cell apoptosis through ROS triggered Cyto-c/Caspase-3 pathway. This study suggests that the melatonin derivative P-3 is likely to become a promising chemical structure for developing the novel anti-cancer agents taking effect through hindering the mutual-promoting processes between inflammation and cancer.
- Ma, Shumeng,Zhu, Longqing,Fan, Xiaohong,Luo, Tian,Liu, Dan,Liang, Ziyi,Hu, Xiaoling,Shi, Tao,Tan, Wen,Wang, Zhen
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- A General and Direct Reductive Amination of Aldehydes and Ketones with Electron-Deficient Anilines
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In our ongoing efforts in preparing tool compounds for investigating and controlling the biosynthesis of phenazines, we recognized the limitations of existing protocols for C-N bond formation of electron-deficient anilines when using reductive amination. After extensive optimization, we have established three robust and scalable protocols for the reductive amination of ketones with electron-deficient anilines, by using either BH3·THF/AcOH/CH2Cl2 (method A), with reaction times of several hours, or the more powerful combinations BH3·THF/TMSCl/DMF (method B) and NaBH4/TMSCl/DMF (method C), which give full conversions for most substrates within 10 to 25 minutes. The scope and limitations of these reactions have been defined for 12 anilines and 14 ketones.
- Pletz, Jakob,Berg, Bernhard,Breinbauer, Rolf
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supporting information
p. 1301 - 1317
(2016/05/02)
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- Sulfonato-Cu(salen) complex catalyzed N-arylation of aliphatic amines with aryl halides in water
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A water-soluble sulfonato-Cu(salen) complex catalyzed procedure for the N-arylation of simple aliphatic amines, amino alcohols and amino acids in pure water have been developed. A variety of substituted aryl iodides, bromides and electron-deficient chlorides were found to be applicable, and 1,2-disubstituted benzimidazoles could be prepared easily by a cascade amination/condensation process in this catalytic system.
- Wu, Zhiqing,Zhou, Li,Jiang, Zhaoqiong,Wu, Di,Li, Zhengkai,Zhou, Xiangge
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experimental part
p. 4971 - 4975
(2010/11/03)
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- Efficient copper-catalyzed synthesis of N-alkylanthranilic acids via an ortho-substituent effect of the carboxyl group of 2-halobenzoic acids at room temperature
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We have developed an efficient copper-catalyzed method for the synthesis of N-alkylanthranilic acids. The protocol uses inexpensive copper(I) iodide/racemic 1,1'-binaphthyl-2,2'-diol (rac-BINOL) as the catalyst/ligand system, readily available 2-halobenzoic acids and aliphatic amines as the starting materials, the coupling reactions were performed at room temperature, and various functionalities in the substrates were tolerated.
- Zeng, Liang,Fu, Hua,Qiao, Renzhong,Jiang, Yuyang,Zhao, Yufen
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supporting information; experimental part
p. 1671 - 1676
(2011/02/25)
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- 2-AMINOBENZAMIDE DERIVATIVE
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To provide a novel and excellent agent for treating or preventing nociceptive pain, neuropathic pain, cancer pain, headache, bladder function disorder and the like, based on the inhibitory action on the capsaicin receptor VR1 activation. The present inven
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Page/Page column 16; 31
(2008/12/07)
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- Regioselective copper-catalyzed C-N and C-S bond formation using amines, thiols and halobenzoic acids
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A regioselective method for highly efficient C-N and C-S bond formation with 2-halobenzoic acids is described. The Cu/Cu2O-catalyzed reaction is carried out in 2-ethoxyethanol or ethylene glycol diethyl ether and does not require the use of strong base or other additives. This procedure eliminates the need for acid protection, tolerates a wide range of functional groups and provides aromatic and aliphatic amines and sulfides in 81-99% yield. Georg Thieme Verlag Stuttgart.
- Liu, Shuanglong,Pestano, John Paul C.,Wolf, Christian
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p. 3519 - 3527
(2008/09/19)
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