- Design, synthesis and evaluation of tetrahydrocarbazole derivatives as potential hypoglycemic agents
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Two series of tetrahydrocarbazole derivatives have been designed and synthesized based on ZG02, a promising candidate developed in our previous studies. The newly prepared compounds were screened for glucose consumption activity in HepG2 cell lines. Aza-tetrahydrocarbazole compound 12b showed the most potent hypoglycemic activity with a 45% increase in glucose consumption when compared to the solvent control, which had approximately 1.2-fold higher activity than the positive control compounds (metformin and ZG02). An investigation of the potential mechanism indicated that 12b may exhibit hypoglycemic activity via activation of the AMPK pathway. Metabolic stability assays revealed that 12b showed good stability profiles in both artificial gastrointestinal fluids and blood plasma from SD rats. An oral glucose tolerance test (OGTT) was performed and the results further confirmed that 12b was a potent hypoglycemic agent.
- Chen, Rui,Cheng, Fei,Cui, Xing,Du, Yao,Fan, Ling-Ling,Guo, Bing,Li, Shu-Min,Tang, Lei,Wang, Jian-Ta,Wang, Li-Li,Wu, Hao-Shu,Yang, Sheng-Gang,Zhang, Ji-Quan,Zhang, Na-Na
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- A metal-free aerobic oxidative bromination of anilines and aryl ketones with 2-methylpyridinium nitrate as a reusable ionic liquid
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An aerobic oxidative bromination of anilines and aryl ketones catalyzed by recyclable 2-methylpyridinium nitrate ionic liquid is achieved in water using hydrobromic acid as the bromine source and molecular oxygen as the oxidant. The catalytic system shows good efficiency and atom economy.
- Li, Ming-Fang,Wang, Jian,Ke, Yong-Xin,Pan, Song-Cheng,Yin, Hong,Du, Wenting,Li, Jing-Hua
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p. 267 - 270
(2020/01/08)
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- AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS
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In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
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Paragraph 0098; 0136; 0137; 0213
(2018/03/25)
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- Method for synthesizing monobrominated aniline compound
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The invention discloses a method for synthesizing a monobrominated aniline compound. The method comprises the following steps: by taking an aniline compound as a raw material, and taking zinc aluminum hydrotalcite ZnAl-BrO3-LDHs with a bromate inserted layer and an alkali metal bromide as bromine sources in a mixed solvent of water and an organic solvent, reacting for 1-3h at 10-50 DEG C; after ending the reaction, extracting a reaction mixed solution A by using dichloromethane; adding a column chromatography silica gel into dichloromethane phase; removing the solvent in the manner of reduced pressure distillation; and acquiring a mono-bromination objective product in the manner of column chromatography separation by using an eluent composed of petroleum ether and ethyl acetate at the ratio of 10:1. The invention realizes a high-selectivity oxidative bromination method by adopting an aniline compound under the effects of ZnAl-BrO3-LDHs and potassium bromide; the monobrominated aniline compound is prepared; the reaction popularity is high and the raw material is low in cost and is easily acquired; the reaction condition is mild; the reaction yield is high; the atom utilization ratio is high; and the chemical selectivity is excellent and the environment is protected.
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Paragraph 0044; 0045; 0046; 0047
(2017/09/26)
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- Design and development of oxobenzimidazoles as novel androgen receptor antagonists
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Antiandrogens are a novel class of anticancer agents that inhibit cancer cell proliferation and induce apoptosis in various cell lines. To find the lead compound from the oxobenzimidazole derivatives, receptor-ligand docking studies were initially performed using Schr?dinger software. The best fit molecules were synthesized and characterized through IR, 1H-NMR, 13C-NMR and HRMS analyses. The structure of compound (9b) was further confirmed by single-crystal XRD analysis. The cell viability of the compounds was determined by MTT assay to find IC50 values against prostate cancer and breast cancer cell lines (PC-3, LNCaP, MCF-7 and MDA-MB-231). The ADME/T property studies were performed to rationalize the inhibitory properties of these compounds. It can be concluded from the study that 9b is the most active compound from the series against PC-3 and LNCaP cell lines.
- Elancheran,Saravanan,Choudhury, Bhaswati,Divakar,Kabilan,Ramanathan,Das, Babulal,Devi,Kotoky, Jibon
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p. 539 - 552
(2016/03/08)
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- SULFONAMIDE COMPOUNDS USEFUL AS CYP17 INHIBITORS
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Disclosed are sulfonamide compounds of Formula (I): or stereoisomers, N-oxides, prodrugs, or pharmaceutically acceptable salts thereof, wherein ring A, R1, R2, R3, R4 and R5 are defined herein. Also disclosed are methods of using such compounds in the treatment of conditions related to CYP17 enzyme, such as cancer, and pharmaceutical compositions comprising such compounds.
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Page/Page column 108
(2012/02/13)
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- Electrophilic bromination of meta-substituted anilines with N-bromosuccinimide: Regioselectivity and solvent effect
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N-Bromosuccinimide-mediated electrophilic aromatic bromination of a series of anilines substituted with an electron-with-drawing group in the meta position was investigated. The regioselectivity of the reaction is markedly dependent on the polarity of the solvent and the bromination reaction can be tuned by appropriate selection of the reaction medium. Georg Thieme Verlag Stuttgart.
- Bartoli, Sandra,Cipollone, Amalia,Squarcia, Antonella,Madami, Andrea,Fattori, Daniela
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experimental part
p. 1305 - 1308
(2009/12/24)
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- Vilsmeier-haack bromination of aromatic compounds with KBr and N-bromosuccinimide under solvent-free conditions
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Bromination of aromatic hydrocarbons is triggered by Vilsmeier-Haack reagent [N,N-dimethyl formamide (DMF-POCl3 system)] in the presence of KBr or N-bromosuccinimide (NBS) under solvent-free conditions by grinding the reactants in a mortar with a pestle. The reactions afforded corresponding bromo derivatives in very good yield with high regioselectivity. The results are comparable with those obtained under reflux conditions. Copyright Taylor & Francis Group, LLC.
- Chakradhar,Roopa,Rajanna,Saiprakash
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experimental part
p. 1817 - 1824
(2009/10/02)
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- Deprotection of N-BOC compounds
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Organic compounds having nitrogen atoms protected with t-butoxycarbonyl are effectively deprotected by heating in a fluorinated alcohol solution.
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Page/Page column 3
(2009/08/18)
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- Deprotection of N-BOC compounds
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Organic compounds having nitrogen atoms protected with t-butoxycarbonyl are effectively deprotected by heating in a fluorinated alcohol solution.
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Page/Page column 5-6
(2009/07/10)
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- Novel practical deprotection of N-Boc compounds using fluorinated alcohols
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The thermolytic deprotection of N-Boc compounds was accomplished using TFE (2,2,2-trifluoroethanol) or HFIP (hexafluoroisopropanol) as solvents. Even though the cleavage of the t-butylcarbamate (Boc) group can be achieved at solvent reflux temperature, the deprotection process was significantly accelerated under microwave-assisted conditions. The practicality of this methodology was demonstrated on alkyl, aryl, and heteroaromatic N-Boc-amines. Copyright Taylor & Francis Group, LLC.
- Choy, Jason,Jaime-Figueroa, Saul,Jiang, Laurence,Wagner, Paul
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p. 3840 - 3853
(2008/12/23)
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- 4- and 5-Substituted 2,3-dihydro-1H-isoindoles, pharmaceutical compositions and method of inhibiting phenylethanolamine N-methyltransferase
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Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase using novel 2,3-dihydro-1H-isoindole compounds having 4- and 5-substituents.
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