951-82-6Relevant articles and documents
One-Pot Biocatalytic In Vivo Methylation-Hydroamination of Bioderived Lignin Monomers to Generate a Key Precursor to L-DOPA
Birmingham, William R.,Galman, James L.,Parmeggiani, Fabio,Seibt, Lisa,Turner, Nicholas J.
, (2022/01/13)
Electron-rich phenolic substrates can be derived from the depolymerisation of lignin feedstocks. Direct biotransformations of the hydroxycinnamic acid monomers obtained can be exploited to produce high-value chemicals, such as α-amino acids, however the reaction is often hampered by the chemical autooxidation in alkaline or harsh reaction media. Regioselective O-methyltransferases (OMTs) are ubiquitous enzymes in natural secondary metabolic pathways utilising an expensive co-substrate S-adenosyl-l-methionine (SAM) as the methylating reagent altering the physicochemical properties of the hydroxycinnamic acids. In this study, we engineered an OMT to accept a variety of electron-rich phenolic substrates, modified a commercial E. coli strain BL21 (DE3) to regenerate SAM in vivo, and combined it with an engineered ammonia lyase to partake in a one-pot, two whole cell enzyme cascade to produce the l-DOPA precursor l-veratrylglycine from lignin-derived ferulic acid.
Anti-acute myeloid leukemia activity of 2-chloro-3-alkyl-1,4-naphthoquinone derivatives through inducing mtDNA damage and GSH depletion
Li, Kun,Yang, Kun,Zheng, Lifang,Li, Yuanyuan,Wang, Qi,Lin, Ruili,He, Dian
, p. 4191 - 4200 (2018/07/21)
2-Chloro-3-alkyl-1,4-naphthoquinone derivatives were synthesized and tested as the anti-acute myeloid leukaemia agents. The compound 9b (2-chloro-3-ethyl-5,6,7-trimethoxy-1,4-naphthoquinone) was the most potent toward HL-60 leukaemia cells. In mechanistic study for 9b, the protein levels of mtDNA-specific DNA polymerase γ (poly-γ) and mtDNA transcription factor A (mt-TFA) were decreased after the 24 h treatment, showing the occurrence of mtDNA damage. And 9b triggered cell cycle arrest at S phase accompanied by a secondary block in G2/M phase which had a direct link to the process of mtDNA damage. The dissipations of mitochondrial membrane potential and ATP also proceeded. On the other hand, 9b promoted the generation of ROS and resulted in the oxidation of intracellular GSH to GSSG. This process was coupled to the formation of adduct between 9b and GSH, detected by the UV–Vis spectrum and HRMS analysis. Depletion of GSH by buthionine sulfoximine enhanced ROS level and produced higher cytotoxicity, suggesting GSH was involved in the anti-leukemic mechanism of 9b. Together, our results provide new insights on the molecular mechanism of the derivatives of 2-chloro-1,4-naphthoquinone and 9b might be useful for the further development into an anti-leukemia agent.
Preparation method of 3,4,5-triethoxy phenylacetic acid
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Paragraph 0011; 0012; 0015, (2017/12/30)
The invention relates to a preparation method of 3,4,5-triethoxy phenylacetic acid. The preparation method is characterized by comprising the following steps: mixing a preheated 3,4,5-triethoxy benzaldehyde, a phase transfer catalyst, chloroform and a preheated alkaline solution into a channel reactor for reaction, adjusting the pH value of a water phase of reaction liquid by virtue of concentrated hydrochloric acid, and cooling for crystallization, so as to obtain 3,4,5-triethoxy mandelic acid or salt; adding 3,4,5-triethoxy mandelic acid or salt and sodium iodide into a polar aprotic solvent, preheating, and inputting the mixture and trimethylchlorosilane into a tubular reactor, so as to obtain a reaction solution; mixing the reaction solution with organic acid, mixing zinc powder with the polar aprotic solvent, and introducing the two mixtures into the channel reactor for reaction so as to obtain reaction liquid; and cooling the reaction liquid for crystallization, filtering, washing a filter cake, combining filtrate, washing, evaporating to obtain a solvent, and carrying out vacuum drying, so as to obtain 3,4,5-triethoxy phenylacetic acid. The preparation method has the advantages that the safety is high, the pollution is low, the cost is low, the yield is high, and the continuous production can be realized.
Nitrogen substitutive 3-oxygen substitutive-6-tetrahydroquinoxaline substitutive structure compound and preparation method and medical application thereof
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Paragraph 0096; 0099, (2017/01/02)
Disclosed are nitrogen substitutive 3-oxygen substitutive-6-tetrahydroquinoxaline substitutive structure compound and preparation method and medical application thereof. The general structure of the compound is as shown in the formula (I). The compound has tubulin polymerization inhibition activities, and is good in tumor disease resistance and proliferative disease apart from tumors.
Synthesis of salidroside analogues and their ability of DPPH radical scavenging activity
Zheng, Cheng,Guo, Yibing,Meng, Ying,Dou, Sufeng,Shao, Jian,Yang, Yumin
, p. 654 - 664 (2013/07/11)
Salidroside is a phenylpropanoid glycoside isolated from Rhodiolarosea L., a traditional Chinese medicinal plant, and has displayed a broad spectrum of pharmacological properties. In this paper, about 22 novel glycosides have been synthesized and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenge activity of each glycoside has been evaluated. 2-(3,4,5-Trihydroxyphenyl)ethyl β-D-galactopyranoside and 3-(3,4,5-trihydroxyphenyl)propyl β-D-glucopyranoside exhibit significant activity prior to salidroside and Vitamin C with EC50 values of 35.85 μM and 36.71 μM, respectively. The results indicate that the phenolic hydroxyl group of these compounds is important for radical scavenging activity and phenyl ring substitution by electron-donating substituents lead to increased antioxidant activity.
Novel hybrids from lamellarin D and combretastatin A 4 as cytotoxic agents
Shen, Li,Yang, Xiaochun,Yang, Bo,He, Qiaojun,Hu, Yongzhou
scheme or table, p. 11 - 18 (2010/03/03)
A new series of hybrids of lamellarin D and combretastatin A 4, 1,2-diphenyl-5,6-dihydropyrrolo [2,1-a] isoquinolines, were designed as cytotoxic agents based on principles of combination in medicinal chemistry and taking the parent compounds' different anti-proliferative mechanisms into consideration. Twenty-two novel hybrids were synthesized through a convenient route, with a key step of core pyrrole formation and evaluated for their anti-proliferative activities in vitro against K-562, A-549, SMMC-7721, SGC-7901 and HCT-116 cancer cell lines. The results showed that some hybrids had good anti-proliferative activities in low IC50 ranges.
Synthetic Studies on Protoberberine Alkaloids
Patra, Amarendra,Mukhopadhyay, Prabir K.,Ghosh, Gargi
, p. 173 - 175 (2007/10/02)
Condensation of homoveratrylamine with substituted isochroman-3-ones (3a-c) affords N-β-(3,4-dimethoxyphenethyl)arylacetamides (4a-c).Treatment of 4a-c with POCl3 and subsequent NaBH4 reduction of the reaction products furnish (+/-)-2,3,9,10,11-pentamethoxytetrahydroprotoberberine (2a), (+/-)-12-hydroxymethyl-2,3,9,10,11-pentamethoxytetrahydroprotoberberine (2b) and (+/-) nor coralydine (2c), respectively.Oxidation of 2a with iodine furnishes 2,3,9,10,11-pentamethoxyprotoberberinium salt (1).Carbon-13 NMR assignments of 2c, 3b, 3c, 4b and 4c are also reported.
A NEW ONE-POT SYNTHESIS OF 1-ARYLMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES FROM ISOQUINOLINIUM SALTS
Iwakuma, Takeo,Yamada, Koichiro,Itoh, Nobuo,Sugasawa, Shigehiko
, p. 1115 - 1118 (2007/10/02)
There has been described a new one-pot synthesis of 1-arylmethyl-1,2,3,4-tetrahydroisoquinoline derivatives by the Barbier reaction of the quaternary salt (4) with various arylmethyl halides followed by reduction with sodium monoacetoxyborohydride.
