3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-ol | 527750-79-4

• 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-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-ol
• 英文别名: 5-[3-Hydroxy-3-(3,4,5-trimethoxyphenyl)propyl]-2-methoxyphenol
• CAS: 527750-79-4
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: CZNLVSFHWATBMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-ol 在 二苯硫醚 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以86.5 %的产率得到3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-one
  参考文献：
  名称：

  毛兰素类似物作为肝癌细胞丙酮酸羧化酶抑制剂的设计、合成及构效关系研究

  摘要：

  基于生物等排原理，通过改变毛兰素的两个芳香环、环上的取代基以及环上的连接基，设计合成了一系列新型毛兰素类似物。该类似物在肝细胞癌细胞中作为丙酮酸羧化酶 (PC) 抑制剂进行了评估。结果发现，用氟取代羟基的化合物35和36在肝癌细胞中表现出比毛兰素更高的活性（IC 50值为17.30 nM），IC 50值分别为15.15 nM和10.05 nM。此外，在10 nM浓度下，化合物35和36对PC的抑制率分别为39.10%和40.15%，表现出与毛兰素几乎相同的抑制活性（抑制率为40.07%）。此外，计算机模拟对接研究证明了受体和配体之间更好相互作用的基础。35的氟原子不仅可以与Lys-1043（NH⋯F，2.04 Å）形成氢键，还可以与Lys-1043（3.67 Å）和Glu-1046（3.70 Å）的羰基形成氟键，由于B环弹头上的卤素的取向不同。相反， 34的氯原子只能与Lys-1043中的

  DOI：

  10.1039/d3ob01114c
• 作为产物：
  描述：

  (E)-3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以68%的产率得到3-(3-hydroxy-4-methoxyphenyl)-1-(3,4,5-trimethoxyphenyl)propan-1-one
  参考文献：
  名称：

  Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity

  摘要：

  The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G(2)/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 mu M; CA4, 0.10 mu M) and compete with [H-3] colchicine for binding to tubulin (8% [H-3] colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.039

文献信息

• Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
  作者：Sylvie Ducki、David Rennison、Meiko Woo、Alexander Kendall、Jérémie Fournier Dit Chabert、Alan T. McGown、Nicholas J. Lawrence

  DOI：10.1016/j.bmc.2009.09.039

  日期：2009.11

  The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G(2)/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 mu M; CA4, 0.10 mu M) and compete with [H-3] colchicine for binding to tubulin (8% [H-3] colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity. (C) 2009 Elsevier Ltd. All rights reserved.
• Design, synthesis and structure–activity relationship studies on erianin analogues as pyruvate carboxylase inhibitors in hepatocellular carcinoma cells
  作者：Hailong Shi、Jinlian Yang、Zeen Qiao、Lingyu Li、Gang Liu、Qi Dai、Li Xu、Wei Jiao、Guolin Zhang、Fei Wang、Xiaoxia Lu、Xiaofeng Ma

  DOI：10.1039/d3ob01114c

  日期：——

  nM) in liver cancer cells with IC50 values of 15.15 nM and 10.05 nM, respectively. Additionally, at a concentration of 10 nM, compounds 35 and 36 inhibited PC with inhibitory rates of 39.10% and 40.15%, respectively, exhibiting nearly identical inhibitory activity to erianin (inhibitory rate of 40.07%). Additionally, a computer simulation docking study demonstrated the basis for better interactions

  基于生物等排原理，通过改变毛兰素的两个芳香环、环上的取代基以及环上的连接基，设计合成了一系列新型毛兰素类似物。该类似物在肝细胞癌细胞中作为丙酮酸羧化酶 (PC) 抑制剂进行了评估。结果发现，用氟取代羟基的化合物35和36在肝癌细胞中表现出比毛兰素更高的活性（IC 50值为17.30 nM），IC 50值分别为15.15 nM和10.05 nM。此外，在10 nM浓度下，化合物35和36对PC的抑制率分别为39.10%和40.15%，表现出与毛兰素几乎相同的抑制活性（抑制率为40.07%）。此外，计算机模拟对接研究证明了受体和配体之间更好相互作用的基础。35的氟原子不仅可以与Lys-1043（NH⋯F，2.04 Å）形成氢键，还可以与Lys-1043（3.67 Å）和Glu-1046（3.70 Å）的羰基形成氟键，由于B环弹头上的卤素的取向不同。相反， 34的氯原子只能与Lys-1043中的