31731-23-4Relevant articles and documents
Iridium-catalyzed highly chemoselective and efficient reduction of nitroalkenes to nitroalkanes in water
Chen, Yang,Liu, Changmeng,Xu, Dong,Xu, Jiaxi,Yang, Zhanhui
supporting information, p. 6050 - 6058 (2021/08/23)
An iridium-catalyzed highly chemoselective and efficient transfer hydrogenation reduction of structurally diverse nitroalkenes was realized at very low catalyst loading (S/C = up to 10000 or 20?000), using formic acid or sodium formate as a traceless hydride donor in water. Excellent functionality tolerance is also observed. The turnover number and turnover frequency of the catalyst reach as high as 18?600 and 19?200 h-1, respectively. An inert atmosphere protection is not required. The reactivities of nitroalkenes are dependent on their substitution pattern, and the pH value is a key factor to accomplish the complete conversion and excellent chemoselectivity. Purification of products is achieved by simple extraction without column chromatography. The reduction procedure is facilely amplified to 10 g scale at 10?000 S/C ratio. The potential of this green reduction in enantioselective hydrogenation has been demonstrated.
2D-2D Nanocomposite of MoS2-Graphitic Carbon Nitride as Multifunctional Catalyst for Sustainable Synthesis of C3-Functionalized Indoles
Bahuguna, Ashish,Kumar, Ashwani,Kumar, Suneel,Chhabra, Tripti,Krishnan, Venkata
, p. 3121 - 3132 (2018/07/29)
A nanocomposite of two-dimensional MoS2 supported on graphitic C3N4 nanosheets has been prepared by a facile ultrasonication method followed by demonstrating its ability to catalyze the synthesis of several indole derivatives. The as-prepared nanocomposite catalyst was characterized in detail by using different microscopic and spectroscopic techniques to understand its structure and physicochemical properties. Subsequently, this nanocomposite catalyst was used as a heterogeneous multifunctional catalyst to synthesize several C3-functionalized indoles in the aqueous medium. The employed strategy also provided very good catalyst recyclability and versatility for the synthesis of various precursors of medicinally significant indoles, such as serotonin, melatonin, and various β-carboline alkaloids. In addition, a natural product derivate has been prepared on the gram-scale by using this methodology. Furthermore, high atom economy (100 %) and lower E-factor (0.042) makes this strategy a sustainable approach for the synthesis of C3-functionalized indoles.
Indole derivative and uses thereof
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, (2017/09/01)
The present invention relates to an indole derivative and uses thereof, wherein the compound and the pharmaceutical composition comprising the compound can be used for antagonizing orexin receptors. The present invention further relates to a method for preparing the compound and the pharmaceutical composition, and uses of the compound and the pharmaceutical composition in treatment or prevention of diseases associated with orexin receptors.
New insights into the catalytic reduction of aliphatic nitro compounds with hypophosphites under ultrasonic irradiation
Letort,Lejeune,Kardos,Métay,Popowycz,Lemaire,Draye
supporting information, p. 4583 - 4590 (2017/10/13)
This work describes an efficient process for the reduction of nitro compounds to the corresponding amines with a catalytic amount of Pd/C (0.6 mol%), and a mixture of sodium hypophosphite and hypophosphorous acid as a reducing agent in H2O/2-MeTHF at 60 °C. The reaction was optimized under silent conditions. The conditions for the in situ production of H2 using the mixture NaH2PO2/H3PO2 were studied. The influence of ultrasonic activation was investigated both in terms of efficiency and kinetics. The reaction was shown to be efficient in water, at 70 °C with a quantitative conversion and a maximal yield in only 15 min thanks to the ultrasonic activation. Finally, ultrasound was proved to act as a physical agent of phase transfer.
Synthesis and anti-inflammatory activity of indole glucosinolates
Vo, Quan V.,Trenerry, Craige,Rochfort, Simone,Wadeson, Jenny,Leyton, Carolina,Hughes, Andrew B.
, p. 856 - 864 (2014/01/23)
The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassici
Dissecting metabolic puzzles through isotope feeding: A novel amino acid in the biosynthetic pathway of the cruciferous phytoalexins rapalexin A and isocyalexin A
Pedras, M. Soledade C.,Yaya, Estifanos E.
, p. 1149 - 1166 (2013/03/29)
Understanding defence pathways of plants is crucial to develop disease-resistant agronomic crops, an important element of sustainable agriculture. For this reason, natural plant defenses such as phytoalexins, involved in protecting plants against microbial pathogens, have enormous biotechnological appeal. Crucifers are economically important plants, with worldwide impact as oilseeds, vegetables of great dietetic value and even nutraceuticals. Notably, the intermediates involved in the biosynthetic pathways of unique cruciferous phytoalexins such as rapalexin A and isocyalexin A remain unknown. Toward this end, using numerous perdeuterated compounds, we have established the potential precursors of these unique phytoalexins and propose for the first time their detailed biosynthetic pathway. This pathway involves a variety of intermediates and a novel amino acid as the central piece of this complex puzzle. This work has set the stage for the discovery of enzymes and genes of the biosynthetic pathway of cruciferous phytoalexins of unique scaffolds.
Total synthesis and biological activity of marine alkaloid eudistomins Y1-Y7 and their analogues
Jin, Huijuan,Zhang, Puyong,Bijian, Krikor,Ren, Sumei,Wan, Shengbiao,Alaoui-Jamali, Moulay A.,Jiang, Tao
, p. 1427 - 1439 (2013/07/11)
Eudistomin Y class compounds are a series of β-carbolines which was originally isolated from a marine turnicate or ascidian near the South Korea Sea. These compounds contain bromo-substituted groups, which is one of the typical characters of marine natural products. We report herein the chemical synthesis and biological evaluation of seven new β-carboline-based metabolites, Eudistomins Y1-Y7, and their hydroxyl-methylated phenyl derivatives. Using bromo-substituted tryptamines and bromo-substituted phenylglyoxals as the key intermediates, Eudistomins Y 1-Y7 and their derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H- and 13C-NMR and mass spectroscopy. Biological studies revealed that all of the compounds showed moderate growth inhibitory activity against breast carcinoma cell line MDA-231 with IC50 of 15-63 μM and the inhibitory activities of hydroxyl-methylated phenyl products were higher than that of the corresponding natural products Eudistomins Y 1-Y7.
Design and bio-evaluation of indole derivatives as potent Kv1.5 inhibitors
Guo, Xiaoke,Yang, Qian,Xu, Jing,Zhang, Li,Chu, Hongxi,Yu, Peng,Zhu, Yingying,Wei, Jinglian,Chen, Weilin,Zhang, Yaozhong,Zhang, Xiaojin,Sun, Haopeng,Tang, Yiqun,You, Qidong
, p. 6466 - 6476 (2013/10/22)
Atrial fibrillation (AF) is one of the common arrhythmias that threaten human health. Kv1.5 potassium channel is reported as an efficacious and safe target for the treatment of AF. In this paper, we designed and synthesized three series of compounds through modifying the lead compound RH01617 that was screened out by the pharmacophore model we reported earlier. All of the compounds were evaluated by the whole-patch lamp technology and most of them possessed potent inhibitory activities against Kv1.5. Compounds IIIi and IIIl were evaluated for the target selectivity as well as the pharmacodynamic effects in an isolated rat model. Due to the promising pharmacological behavior, compound IIIl deserves further pharmacodynamic and pharmacokinetic evaluations.
New approach to oximes through reduction of nitro compounds enabled by visible light photoredox catalysis
Cai, Shunyou,Zhang, Shaolong,Zhao, Yaohong,Wang, David Zhigang
supporting information, p. 2660 - 2663 (2013/07/11)
A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)3Cl2 photocatalyst, Hünig's base, Mg(ClO 4)2 activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated with classical Beckmann rearrangement, enables such high-value industrial feedstock as caprolactam to be readily accessed from simple precursor nitrocyclohexane.
Visible-light-promoted C-C bond cleavage: Photocatalytic generation of iminium ions and amino radicals
Cai, Shunyou,Zhao, Xinyang,Wang, Xinbo,Liu, Qisong,Li, Zigang,Wang, David Zhigang
supporting information; experimental part, p. 8050 - 8053 (2012/08/29)
Photoscissors: Structurally variable and synthetically robust iminium ions and amino radicals species could be simultaneously generated by visible-light-promoted photoredox cleavage of the C-C bonds in simple vicinal diamine precursors under very mild reaction conditions. Copyright
