118-41-2Relevant articles and documents
Cloning and heterologous expression of two aryl-aldehyde dehydrogenases from the white-rot basidiomycete Phanerochaete chrysosporium
Nakamura, Tomofumi,Ichinose, Hirofumi,Wariishi, Hiroyuki
, p. 470 - 475 (2010)
We identified two aryl-aldehyde dehydrogenase proteins (PcALDH1 and PcALDH2) from the white-rot basidiomycete Phanerochaete chrysosporium. Both PcALDHs were translationally up-regulated in response to exogenous addition of vanillin, one of the key aromatic compounds in the pathway of lignin degradation by basidiomycetes. To clarify the catalytic functions of PcALDHs, we isolated full-length cDNAs encoding these proteins and heterologously expressed the recombinant enzymes using a pET/Escherichia coli system. The open reading frames of both PcALDH1 and PcALDH2 consisted of 1503 nucleotides. The deduced amino acid sequences of both proteins showed high homologies with aryl-aldehyde dehydrogenases from other organisms and contained ten conserved domains of ALDHs. Moreover, a novel glycine-rich motif "GxGxxxG" was located at the NAD+-binding site. The recombinant PcALDHs catalyzed dehydrogenation reactions of several aryl-aldehyde compounds, including vanillin, to their corresponding aromatic acids. These results strongly suggested that PcALDHs metabolize aryl-aldehyde compounds generated during fungal degradation of lignin and various aromatic xenobiotics.
One pot synthesis of α-aminophosphonates containing bromo and 3,4,5-trimethoxybenzyl groups under solvent-free conditions
Li, Caihong,Song, Baoan,Yan, Kai,Xu, Gangfang,Hu, Deyu,Yang, Song,Jin, Linhong,Xue, Wei,Lu, Ping
, p. 163 - 172 (2007)
New α-aminophosphonates were synthesized by the Kabachnik-Fields reaction of 3,4,5-trimethoxybenzaldehyde (TMB) with p- or m-bromoaniline and a dialkyl phosphite under solvent-free conditions. TMB was prepared from gallic acid via a four step synthetic sequence involving etherification, esterification, hydrazidation and potassium ferricyanide oxidation. The structures of all synthesized compounds were confirmed by elemental analysis, IR, 1H-, 13C- and 31P-NMR spectral data. Compound 7g was also characterized by X-ray crystallography. A half-leaf method was used to determine the in vivo curative efficacy of the eight title products against tobacco mosaic virus (TMV). It was found that compounds 7g and 7h possess good in vivo curative effects against TMV.
New flavones from Bauhinia championii Benth
Chen,Chen,Hsu,Chen
, p. 166 - 169 (1984)
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Herzig,Tscherne
, p. 991 (1905)
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The Selective Liquid-Phase Oxidation of 3,4,5-Trimethoxytoluene to 3,4,5-Trimethoxybezaldehyde
Kitajima, Nobumasa,Takemura, Kazuya,Moro-Oka, Yoshihiko,Yoshikuni, Tadatsugu,Akada, Mitsuo,et al.
, p. 1035 - 1038 (1988)
The selective liquid-phase oxidation of 3,4,5-trimethoxytoluene to 3,4,5-trimethoxybenzaldehyde, an important chemical intermediate for medicine production, was developed; when 2.0 mmol of the reactant was heated at 110 deg C for 2 h in an autoclave under 3 atm O2 with 10 ml of acetic acid in the presence of 0.75 mmol of Co(OAc)2-Mn(OAc)2 (3:1 mol ratio), a 92percent yield of the aldehyde was obtained.
Solvolysis, Electrochemistry, and Development of Synthetic Building Blocks from Sawdust
Nguyen, Bichlien H.,Perkins, Robert J.,Smith, Jake A.,Moeller, Kevin D.
, p. 11953 - 11962 (2015)
Either aldehyde or cinnamyl ether products can be selectively extracted from raw sawdust by controlling the temperature and pressure of a solvolysis reaction. These materials have been used as platform chemicals for the synthesis of 15 different synthetic substrates. The conversion of the initial sawdust-derived materials into electron-rich aryl substrates often requires the use of oxidation and reduction chemistry, and the role electrochemistry can play as a sustainable method for these transformations has been defined.
Synthesis and antitumor activity of novel 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives
Liu, Fang,Huai, Ziyou,Xia, Guotai,Song, Liuping,Li, Sha,Xu, Yulan,Hong, Kangjun,Yao, Mingyue,Liu, Gang,Huang, Yinjiu
, p. 2561 - 2565 (2018)
A series of 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives were synthesized as epidermal growth factor receptor (EGFR) inhibitors, and their antitumor activities were assessed in the gastric cancer cell line SGC7901 using MTT assay. All compounds of Tg1–14 were found to inhibit SGC7901 cell proliferation, and compound Tg11 (IC50 = 0.434 μM) was found to be slightly more effective against SGC7901 cells than epirubicin (IC50 = 5.16 μM). This suggests that compound Tg11 can be used as a new substitution structure to develop more efficacious antitumor agents. Western blot analysis showed that treatment with Tg11 (40 μM for 30 min) resulted in near complete inhibition of EGF-induced ERK1/2 phosphorylation, indicating that its anti-proliferative effect is largely associated with inhibition of ERK1/2 activation. These data imply that Tg11 is a potential anticancer agent capable of inhibiting cell proliferation.
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Saidkhodzhaev et al.
, (1978)
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Subramanian,Nair
, p. 1679 (1971)
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Synthesis and antioxidant activities of berberine 9-: O -benzoic acid derivatives
Liu, Yanfei,Long, Shuo,Zhang, Shanshan,Tan, Yifu,Wang, Ting,Wu, Yuwei,Jiang, Ting,Liu, Xiaoqin,Peng, Dongming,Liu, Zhenbao
, p. 17611 - 17621 (2021/05/29)
Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.
Oxidative carbon-carbon bond cleavage of 1,2-diols to carboxylic acids/ketones by an inorganic-ligand supported iron catalyst
Chen, Weiming,Xie, Xin,Zhang, Jian,Qu, Jian,Luo, Can,Lai, Yaozhu,Jiang, Feng,Yu, Han,Wei, Yongge
supporting information, p. 9140 - 9146 (2021/11/23)
The carbon-carbon bond cleavage of 1,2-diols is an important chemical transformation. Although traditional stoichiometric and catalytic oxidation methods have been widely used for this transformation, an efficient and valuable method should be further explored from the views of reusable catalysts, less waste, and convenient procedures. Herein an inorganic-ligand supported iron catalyst (NH4)3[FeMo6O18(OH)6]·7H2O was described as a heterogeneous molecular catalyst in acetic acid for this transformation in which hydrogen peroxide was used as the terminal oxidant. Under the optimized reaction conditions, carbon-carbon bond cleavage of 1,2-diols could be achieved in almost all cases and carboxylic acids or ketones could be afforded with a high conversion rate and high selectivity. Furthermore, the catalytic system was used efficiently to degrade renewable biomass oleic acid. Mechanistic insights based on the observation of the possible intermediates and control experiments are presented.
