3,4,2',4',6'-pentamethoxymethoxychalcone | 91299-69-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3,4,2',4',6'-pentamethoxymethoxychalcone
• 英文别名: 3-[3,4-bis(methoxymethoxy)phenyl]-1-[2,4,6-tris(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 91299-69-3
• 化学式: C₂₅H₃₂O₁₁
• 分子量: 508.522
• InChiKey: ZUEYMGZONTVTGU-UHFFFAOYSA-N

物化性质

• 沸点：
  634.5±55.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  36.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  109.37
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3,4,2',4',6'-pentamethoxymethoxychalcone 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3,4,2',4',6'-pentamethoxymethoxychalcone epoxide
  参考文献：
  名称：

  Design, Synthesis, and Examination of Neuron Protective Properties of Alkenylated and Amidated Dehydro-Silybin Derivatives

  摘要：

  A series of C7-O- and C20-O-amidated 2,3-dehydrosilybin (DHS) derivatives ((+/-)-1a-f and (+/-)-2), as well its it set of alkenylated DHS analogues ((+/-)-4a-f), were designed and de novo synthesized. A diesteric derivative of DHS ((+/-)-3) and two C23 esterified DHS analogues ((+/-)-5a and (+/-)-5b) were also prepared for comparison. The cell viability of PC12 cells, Fe2+ chelation, lipid peroxiclation (LPO), freeradical scavenging, and xanthine oxidase inhibition models were utilized to evaluate their antioxidative and neuron protective properties. The study revealed that the diether at C7-OH and C20-OH as well as the monoether at C7-OH, which possess aliphatic substituted acetamides, demonstrated more potent LPO inhibition and Fe2+ chelation compared to DHS and quercetin. Conversely, the diallyl ether at C7-OH and C20-OH wits more potent in protection of PCl2 cells against H2O2-induced injury than DHS and quercetin. Overall, the more lipophilic alkenylated DHS analogues were better performing neuroprotective agents than the acetamidated derivatives. The results in this study would be beneficial for optimizing the therapeutic potential of lignoflavonoids, especially in neurodegenerative disorders such as Alzheimer's and Parkinson's disease.

  DOI：

  10.1021/jm900735p
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 3.75h， 生成 3,4,2',4',6'-pentamethoxymethoxychalcone
  参考文献：
  名称：

  Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship

  摘要：

  To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.042

文献信息

• Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs
  作者：N. Pandurangan、Chinchu Bose、A. Banerji

  DOI：10.1016/j.bmcl.2011.07.008

  日期：2011.9

  A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, synthesis and bioactivity of chalcones and its analogues
  作者：Chao Niu、Adila Tuerxuntayi、Gen Li、Madina Kabas、Chang-Zhi Dong、Haji Akber Aisa

  DOI：10.1016/j.cclet.2017.03.018

  日期：2017.7

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• PROCESS FOR TOTAL SYNTHESIS OF FLAVONOID COMPOUNDS AND ISOMERS THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20160362401A1

  公开（公告）日：2016-12-15

  The present invention relates to the a process for total synthesis of flavonoid compounds of general formula I and isomers thereof wherein R 1 and R 2 is OH; R 3 ═H or The present invention particularly relates to the process for preparation and separation of (2S,3S)-taxifolin-6-C-β-D-glucopyranoside (ulmoside A), (2R,3R)-taxifolin-6-C-β-D-glucopyranoside and taxifolin.
• US9611255B2
  申请人：——

  公开号：US9611255B2

  公开（公告）日：2017-04-04