- Synthesis and anti-acetylcholinesterase activity of scopoletin derivatives
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A series of scopoletin derivatives incorporated with the pyridinium moiety was synthesized and evaluated for their acetylcholinesterase (AChE) inhibitory activity by the colorimetric Ellman's method. A 2-fluorobenzylpyridinium derivative was the most potent among the tested compounds, with an IC50 value of 0.215 ± 0.015 μM, which was greatly improved from that of scopoletin. Docking studies revealed that the scopoletin portion of the mentioned compound was bound to the peripheral anionic site of the AChE, whereas the N-benzylpyridinium residue to the catalytic anionic site.
- Khunnawutmanotham, Nisachon,Chimnoi, Nitirat,Saparpakorn, Patchreenart,Techasakul, Supanna
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- Synthetic method for rugchalcone A, B and their derivatives and their anti-inflammatory use
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The present invention provides an effective anti-inflammatory agent which does not have a side effect. The present inventors have invented an effective method for synthesizing 2-aroylbenzofuran, rugchalcone A, B, and a derivative thereof at high yield by a Rap-Stoermer reaction between substituted salicylaldehyde and phenacyl bromide. Moreover, the inventors have evaluated an anti-inflammatory effect of the compound in lipopolysaccharide-induced RAW 264.7 macrophages. The compound remarkably inhibits the generation of nitrogen oxide which mediates inflammation without having cytotoxicity at a concentration of 10 andmu;M, and an IC_50 value is in the range of 0.57-13.27 andmu;M. From 2-aroylbenzofuran synthesized according to the preset invention, compound 4 (99.6%; IC_50 = 0.57), rugchalcone B (compound 2)(99.3%; IC_50 = 4.13), compound 7 (96.8%; IC_50 = 1.90), and compound 8 (74.3%; IC_50 = 0.99) show a maximum inhibiting activity. Such a result shows that compounds 2, 4, 7, and 8 having 4-hydroxyphenyl group and/or a hydroxyl group in a 5- and/or 6- position of a benzofuran motif can be functioned as a structure needed in developing an iNOS inhibitor with respect to the application thereof to the anti-inflammatory field.COPYRIGHT KIPO 2017
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- Synthesis and biological evaluation of 2-aroylbenzofurans, rugchalcones A, B and their derivatives as potent anti-inflammatory agents
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An efficient synthesis of 2-aroylbenzofurans, rugchalcones A, B and their derivatives was accomplished in excellent yields by the Rap–Stoermer reaction between substituted salicylaldehydes and phenacyl bromides. Later their anti-inflammatory effects were evaluated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. The compounds were exhibited exceptional potency against inflammatory mediated NO production with no cytotoxicity at 10?μM concentration and IC50values are found in the range from 0.75 to 13.27?μM. Among the 2-aroylbenzofurans prepared in this study, compounds 4 (99.6%; IC50?=?0.57), rugchalcone B (2) (99.3%; IC50?=?4.13), 7 (96.8%; IC50?=?1.90) and 8 (74.3%; IC50?=?0.99) were showed the maximum inhibitory activity. This study suggests that compounds 2, 4, 7 and 8 which are having 4-hydroxyphenyl group and/or hydroxy (–OH) group at 5- and/or 6-position of benzofuran motif could be considered as a promising scaffolds for the further development of iNOS inhibitors for potential anti-inflammatory applications.
- Seo, Young Hwa,Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
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p. 1521 - 1524
(2016/07/29)
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- Divergent and concise total syntheses of dihydrochalcones and 5-deoxyflavones recently isolated from Tacca species and Mimosa diplotricha
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Dihydrochalcones and 5-deoxyflavones are types of compounds possessing various biologically interesting properties. Herein, we report the concise and divergent total syntheses of several naturally occurring dihydrochalcones and 5-deoxyflavones from readily available starting materials. The divergent strategy is based around manipulation of a common chalcone scaffold and features application of Algar-Flynn-Oyamada oxidation and benzoquinone C-H activation methodologies. These are the first reported total syntheses of these biologically interesting compounds and the concise and flexible route should be readily amenable to future analogue generation. Furthermore, this work provides an illustration of the utility of divergent synthesis for the expedient and step-economical preparation of natural product libraries.
- Sum, Tze Han,Sum, Tze Jing,Stokes, Jamie E.,Galloway, Warren R.J.D.,Spring, David R.
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p. 4557 - 4564
(2015/06/08)
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- Efficient preparation of ((3-chloro-2-fluorophenyl)-[7-methoxy-8-(3- morpholin-4-yl-propoxy)-10,11-dihydro-5-oxa-2,4,11-triazadibenzo(a,d) cyclohepten-1-yl]-amine) for in-vivo study
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An improved route for the preparation of highly functionalized 5,6-dihydropyrimido[4,5-b][1,4]oxazepine 1a in multigram quantities was developed. This new methodology was highlighted by the proper methoxy disposition via a regioselective methylation of 2,4,5-trihydroxy-benzaldehyde followed by a magnesium sulfate-promoted cyclization. Copyright Taylor & Francis LLC.
- Liu, Hu,Smith II, Leon M.,Mao, Yunyu,Pan, Weitao,Xu, Yong-Jiang,Burdzovic-Wizeman, Sabina,Duncton, Matthew A. J.,Wong, Wai C.
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p. 347 - 354
(2007/10/03)
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- PROCESS FOR PREPARATION OF ESCULETIN COMPOUNDS, ESCULETIN COMPOUNDS AND INTERMEDIATES THEREOF, AND USE OF BOTH
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An esculetin compound, an intermediate thereof, a process for manufacturing an esculetin compound, and an antifungal composition for agriculture and horticulture and an herbicide comprising an esculetin compound or an intermediate thereof are provided. The process for manufacturing an esculetin compound is a low-cost, high-yield, and industrially practicable process, and comprises the following step.A process for manufacturing an esculetin compound of the formula (2): characterized by cyclizing a trihydroxybenzaldehyde compound of the formula (1): in an aprotic polar solvent in the presence of a weak base, with acetic anhydride or the like.
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Page/Page column 13
(2010/01/31)
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