(E)‐4‐(4‐hydroxy‐3,5‐dimethoxyphenyl)but‐3‐en‐2‐one | 203194-42-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)‐4‐(4‐hydroxy‐3,5‐dimethoxyphenyl)but‐3‐en‐2‐one
• 英文别名: (E)-4-(4-hydroxy-3,5-dimethoxyphenyl)but-3-en-2-one；1t-(4-hydroxy-3.5-dimethoxy-phenyl)-buten-(1)-one-(3)；1t-(4-Hydroxy-3.5-dimethoxy-phenyl)-buten-(1)-on-(3)；4-(3,5-Dimethoxy-4-hydroxyphenyl)-3-buten-2-one
• CAS: 203194-42-7
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: OOFWCWCUKUVTKD-SNAWJCMRSA-N

物化性质

• 沸点：
  381.5±37.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)‐4‐(4‐hydroxy‐3,5‐dimethoxyphenyl)but‐3‐en‐2‐one 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 (E)-4-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]but-3-en-2-one
  参考文献：
  名称：

  Effect of Phenolic Glycosides on Agrobacterium tumefaciens virH Gene Induction and Plant Transformation

  摘要：

  O-Aryl-D-glucoside (4-7) and D-xyloside (8-10) derivatives were synthesized and tested on Agrobacterium virH gene induction and plant transformation. alpha- or beta-Glycosides enhanced vir activity at concentrations above 250 muM. The highest vir activity was observed with beta-glucoside derivative 4 at 10 mM. A marked difference between phenol glucoside derivative 4 and the corresponding free phenol on the growth of transformants was observed. The regenerated transgenic tissues, after transformation on medium containing acetosyringyl beta-glucoside 4, grew at twice the rate of those on medium containing only free acetosyringone (AS). Compound 4 was less toxic for tobacco explants compared to the corresponding free phenol. However, the xyloside derivatives tested (8-10) were less effective for gene induction compared with corresponding free phenols.

  DOI：

  10.1021/np030281z
• 作为产物：
  描述：

  4-乙酰氧基-3,5-二甲氧基苯甲酰氯 在 sodium hydroxide 、 Pd-BaSO₄ 、 xylene 作用下， 生成 (E)‐4‐(4‐hydroxy‐3,5‐dimethoxyphenyl)but‐3‐en‐2‐one
  参考文献：
  名称：

  Imaki et al., Nippon Nogeikagaku Kaishi, 1944, vol. 20, p. 289,292

  摘要：

  DOI：

文献信息

• Novel vacuum stable ketone-based matrices for high spatial resolution MALDI imaging mass spectrometry
  作者：Junhai Yang、Jeremy L. Norris、Richard Caprioli

  DOI：10.1002/jms.4277

  日期：2018.10

  describe the use of aromatic ketones and cinnamyl ketones that have high vacuum stability for analyzing tissue sections using matrix‐assisted laser desorption/ionization imaging mass spectrometry. Specifically, the matrix, (E)‐4‐(2,5‐dihydroxyphenyl)but‐3‐en‐2‐one (2,5‐cDHA) provides high sensitivity and high vacuum stability while producing small size crystals (1‐2 μm). A high throughput and highly reproducible

  我们描述了使用具有高真空稳定性的芳族酮和肉桂基酮，通过基质辅助激光解吸/电离成像质谱分析组织切片。具体而言，基质（E）-4-（2,5-二羟基苯基）但是-3-烯-2-酮（2,5-cDHA）提供高灵敏度和高真空稳定性，同时生成小尺寸晶体（1-2微米）。针对这些基质开发了一种高通量和高度可重复的样品制备方法，该方法首先涉及使用有机喷雾溶液进行小的基质晶体播种，然后将基质以30％乙腈/ 70％水溶液喷雾在组织表面上以获得小晶体的均匀涂层，适用于高空间分辨率成像。
• Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs
  作者：Wenfei He、Jingsong Wang、Qiling Jin、Jiafeng Zhang、Yugang Liu、Zewu Jin、Hua Wang、Linya Hu、Lu Zhu、Mengya Shen、Lili Huang、Shengwei Huang、Wulan Li、Qichuan Zhuge、Jianzhang Wu

  DOI：10.1016/j.bioorg.2021.105080

  日期：2021.9

  of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and

  高效低毒的抗氧化剂具有治疗脑缺血再灌注损伤（CIRI）的潜力。二烯酮单羰基姜黄素类似物 (DMCA) 能够克服姜黄素的不稳定性和药代动力学缺陷，具有显着的抗氧化活性，但被发现具有显着毒性。在这项研究中，基于 DMCA 骨架设计了一种具有降低毒性和提高稳定性的单烯酮单羰基姜黄素类似物 sAc 的新型骨架。此外，通过应用绿色、简单、经济的合成方法，获得了 32 种 sAc 类似物。使用 H 2 O 2筛选在 PC12 细胞中具有抗氧化保护作用的多种 sAc 类似物诱导氧化应激损伤模型， 通过随机森林算法（RF）建立回归系数为R 2 = 0.918921的构效关系（QSAR）定量评价模型。在这些化合物中，最佳活性化合物sAc15通过激活 Nrf2/HO-1 抗氧化信号通路，有效消除响应氧化应激损伤的 ROS 生成，从而对 PC12 细胞的细胞生长产生有效的保护作用。此外，sAc15在小鼠大脑中动脉闭塞
• Design, synthesis, in vitro and in silico evaluation of anti-colorectal cancer activity of curcumin analogues containing 1,3-diphenyl-1H-pyrazole targeting EGFR tyrosine kinase
  作者：Nam Q.H. Doan、Ngan T.K. Nguyen、Ngoc B. Nguyen、Thi T. Tran、Quang N. Tran、Tuyen N. Truong

  DOI：10.1016/j.bbagen.2023.130414

  日期：2023.9

  Recent studies have shown that monocarbonyl analogues of curcumin (MACs) and 1H-pyrazole heterocycle both demonstrated promising anticancer activities, in which several compounds containing these scaffolds could target EGFR. In this research, 24 curcumin analogues containing 1H-pyrazole (a1-f4) were synthesized and characterized by using modern spectroscopic techniques. Firstly, synthetic MACs were

  最近的研究表明，姜黄素的单羰基类似物（MAC）和1H-吡唑杂环均表现出良好的抗癌活性，其中几种含有这些支架的化合物可以靶向EGFR。本研究利用现代光谱技术合成并表征了24种含有1H-吡唑( a1 - f4 )的姜黄素类似物。首先，筛选了合成的 MAC 对人类癌细胞系（如 SW480、MDA-MB-231 和 A549）的细胞毒性，从中鉴定和选择了 10 种最有潜力的细胞毒性化合物。随后，进一步筛选所选 MAC 对酪氨酸激酶的抑制作用，结果表明a4对 EGFR WT和 EGFR L858R表现出最显着的抑制作用。基于这些结果，a4进一步证明了其引起形态变化、增加凋亡细胞百分比以及增加caspase-3活性的能力，表明其对SW480细胞具有诱导凋亡的活性。此外，a4对SW480细胞周期的影响揭示了其将SW480细胞阻滞在G 2 /M期的能力。在随后的基于计算机的评估中，a4预计具有多种有前景的
• Synthesis and cell growth inhibitory properties of substituted (E)-1-phenylbut-1-en-3-ones
  作者：Sylvie Ducki、John A. Hadfield、Lucy A. Hepworth、Nicholas J. Lawrence、Ching-Ying Liu、Alan T. McGown

  DOI：10.1016/s0960-894x(97)10147-0

  日期：1997.12

  A series of (E)-1-phenylbut-1-en-3-ones, based on the naturally occurring (E)-1-(4'-hydroxyphenyl)but-1-en-3-one [IC50 (K562) 60 mu M], was synthesised and screened for cytotoxic activity against the K562 human leukaemia cell line. (E)-1-(Pentafluorophenyl)but-1-en-3-one [IC50 (K562) 1.8 mu M] was found to be over 30-fold more active than 1. (C) 1997 Elsevier Science Ltd.
• Rajakumar; Rao, Pharmazie, 1994, vol. 49, # 7, p. 516 - 519
  作者：Rajakumar、Rao

  DOI：——

  日期：——