- First synthesis of tabamides A–C and their derivatives: In vitro nitric oxide inhibitory activity
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The first synthesis of natural phenolic amides, tabamides A–C (1–3), and their derivatives (4–12) was accomplished using Stobbe condensation and amide coupling reactions as key steps. The in vitro nitric oxide (NO) inhibitory effects of these compounds in LPS-induced RAW-264.7 macrophages were evaluated as an indicator of anti-inflammatory activity. All compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without significant cytotoxicity. Compound 6, a tabamide A derivative (IC50 = 82.6 μM), followed by tabamide A (1, IC50 = 100.7 μM), was the most potent from the series. The present study revealed that tabamide A (1) could be considered as a lead structure to develop NO production-targeted anti-inflammatory agents.
- Damodar, Kongara,Shin, Sooyong,Jeon, Sung Ho,Lee, Jeong Tae
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supporting information
(2021/11/10)
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- Synthesis of Polysubstituted 3-Methylisoquinolines through the 6π-Electron Cyclization/Elimination of 1-Azatrienes derived from 1,1-Dimethylhydrazine
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A convenient one pot microwave-assisted 6π-electron cyclization/aromatization approach toward 3-methylisoquinolines is reported. The starting 1-azatriene derivatives were prepared in situ by reaction of 2-propenylbenzaldehydes with 1,1-dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4-dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.
- Vargas, Didier F.,Larghi, Enrique L.,Kaufman, Teodoro S.
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supporting information
p. 5605 - 5614
(2018/10/09)
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- Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry
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The title natural products (1 and 2, respectively) have been synthesized by Au(I)-catalyzed intramolecular hydroarylation (IMHA) of the relevant aryl propiolate esters (e.g., 13), which were themselves formed by reaction of the corresponding phenols with either 3-(trimethylsilyl)propiolic acid or propiolic acid and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride or dicyclohexylcarbodiimide. (±)-Purpurasol (3) was readily derived from fraxetin (2) by established procedures.
- Cervi, Aymeric,Aillard, Paul,Hazeri, Nourallah,Petit, Laurent,Chai, Christina L. L.,Willis, Anthony C.,Banwell, Martin G.
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p. 9876 - 9882
(2013/10/22)
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- An efficient synthesis of a potent anti-inflammatory agent, viscolin, and its inducible nitric oxide synthase inhibitory activity
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A new and efficient synthetic pathway employed the aldol condensation between the acetophenone (3) and vanillin derivative (4) resulted in the precursor chalcone intermediate (14). The target compound viscolin (1) could be afforded through the hydrogenation of the chalcone and followed by deprotection. The present strategy described the development of a more efficient procedure that allowed large-scale production of viscolin for the further research of biological activity both in vitro and in vivo.
- Kuo, Ping-Chung,Chen, Yi-Hsien,Leu, Yann-Lii,Huang, Chieh-Hung,Liao, Yu-Ren,Lee, E.-Jian,Yang, Mei-Lin,Wu, Tian-Shung
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experimental part
p. 557 - 561
(2012/06/01)
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- A concise synthesis of viscolin, and its anti-inflammatory effects through the suppression of iNOS, COX-2, ERK phosphorylation and proinflammatory cytokines expressions
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In the present report, a concise synthesis of viscolin (1) has been achieved. The anti-inflammatory effect of viscolin was investigated in vitro and in vivo. Viscolin blocked the expression of iNOS and COX-2, and it also inhibited the ERK for the activation of NF-κB in LPS-stimulated RAW 264.7 macrophages. Western blotting and immunohistochemical analysis revealed that viscolin decreased Carr-induced iNOS and COX-2 expressions. These results could help to deduce the anti-inflammatory mechanisms.
- Huang, Guan-Jhong,Bhaskar Reddy, M. Vijaya,Kuo, Ping-Chung,Huang, Chieh-Hung,Shih, Hung-Cheng,Lee, E.-Jian,Yang, Mei-Lin,Leu, Yann-Lii,Wu, Tian-Shung
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p. 371 - 378
(2012/03/26)
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- A convenient synthesis of 3,4-dimethoxy-5-hydroxybenzaldehyde
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Synthesis of 3,4-dimethoxy-5-hydroxybenzaldehyde (1) in three steps from vanillin with the key step being a copper catalyzed hydrolysis of 5- bromovanillin to give 4,5-dihydroxy-3-methoxybenzaldehyde.
- Ellis, James E.,Lenger, Steven R.
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p. 1517 - 1524
(2007/10/03)
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- Radiation-induced effects in lignin model compounds: A pulse and steady-state radiolysis study
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A lignin model compound β-(2-methoxyphenoxy)-3,4-dimethoxyacetophenone (1) was subjected to 60Co gamma irradiation and pulse radiolysis under different conditions (dose, medium, pH). interaction with hydroxyl radicals resulted in aryl hydroxylation, fragmentation, and cleavage. A hydroxylation-cleavage pathway was found at all pH values. At alkaline pH, fragmentation reactions were also observed. The predominant reaction with solvated electrons was fragmentation of the β-aryl ether bond followed by cleavage reactions.
- Chuaqui,Rajagopal,Kovacs,Stepanik,Merritt,Gyorgy,Whitehouse,Ewing
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p. 9689 - 9698
(2007/10/02)
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- Aromatic Hydroxylation. Hydroxybenzaldehydes from Bromobenzaldehydes via Reaction of in Situ Generated, Lithiated α-Morpholinobenzyl Alkoxides with Nitrobenzene
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A general method for the one-step conversion of bromobenzaldehydes to the corresponding hydroxybenzaldehydes has been developed.The method involves in situ protection of the aldehyde function of the bromobenzaldehyde as its lithium morpholinoalkoxide, followed by lithium-bromine exchange, reaction with nitrobenzene at -75 deg C, and a subsequent acidic workup.The method has been applied to the synthesis of 4,5-dimethoxy-3-hydroxy- (1a), 3,5-dimethoxy-2-hydroxy- (2a), 3,5-bis(benzyloxy)-2-hydroxy- (2b), 3,4-dimethoxy-2-hydroxy- (14), 3-hydroxy-4,5-(methylenedioxy)- (16), and 4,5-dimethoxy-2-hydroxybenzaldehydes (18) from the bromobenzaldehydes 4, 12a, 12b, 13, 15, and 17, respectively.
- Sinhababu, Achintya K.,Borchardt, Ronald T.
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p. 1941 - 1944
(2007/10/02)
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- SYNTHESIS OF 6,7,2',3'-TETRAMETHOXY-5,4',6'-TRIHYDROXYFLAVONE
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6,7,2',3'-Tetramethoxy-5,4',6'-trihydroxyflavone and its positional isomers were synthesized, and any of them were not identical with the flavone isolated from Notholaena aschenborniana.
- Iinuma, Munekazu,Tanaka, Toshiyuki,Matsuura, Shin
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p. 2425 - 2428
(2007/10/02)
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