(E)-1-[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]-6-phenylhex-1-en-3-ol | 911682-28-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-1-[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]-6-phenylhex-1-en-3-ol
• CAS: 911682-28-5
• 化学式: C₂₅H₃₆O₃Si
• 分子量: 412.645
• InChiKey: JTVKVBBOYNCVEG-BMRADRMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]-6-phenylhex-1-en-3-ol 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 Phenethyl-thiocarbamic acid O-(1-{2-[4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-ethyl}-4-phenyl-butyl) ester
  参考文献：
  名称：

  Chain-Branched acyclic phenethylthiocarbamates as vanilloid receptor antagonists

  摘要：

  A series of acyclic phenethylthiocarbamate derivatives have been synthesized, and their antagonist effect against vanilloid receptor tested. Chain branching led to a significant change in antagonist activity of the parent molecule. Ethyl-branched le showed a 6.3 muM Of IC50 value in Ca-45(2+)-influx assay. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00178-1
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 作用下， 生成 (E)-1-[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]-6-phenylhex-1-en-3-ol
  参考文献：
  名称：

  Suppression of Inducible Nitric Oxide Synthase Expression by Yakuchinones and Their Analogues

  摘要：

  合成了类黄酮化合物作为抑制脂多糖激活的巨噬细胞系RAW 264.7细胞中一氧化氮产生的抑制剂。我们制备了比来自毛竹（Alpinia oxyphylla）的天然分子黄酮A和B更强的抑制剂。通过对类化合物的有限结构活性关系研究，我们得出结论：维持两个芳基之间的连接链的最佳长度以及连接链中存在烯酮基团对活性至关重要。最有效结构的IC50值为0.92μM。活性类化合物抑制了诱导型一氧化氮合酶蛋白及其mRNA的表达。

  DOI：

  10.1248/cpb.54.377

文献信息

• Suppression of Inducible Nitric Oxide Synthase Expression by Yakuchinones and Their Analogues
  作者：Hwa Jin Lee、Ji Sun Kim、Joung Wha Yoon、Hee-Doo Kim、Jae-Ha Ryu

  DOI：10.1248/cpb.54.377

  日期：——

  Analogues of yakuchinones were synthesized as inhibitors of nitric oxide production in lipopolysaccharide-activated macrophage cell line, RAW 264.7 cells. We prepared stronger inhibitors than the original natural molecules, yakuchinones A and B reported from Alpinia oxyphylla. From the limited structural activity relation study of analogues, we concluded that the optimal length of linker between two aryl groups and the presence of enone moiety in the linker were identified as essential for the activity. The IC50 value of the most potent structure was 0.92 μM. The active analogues suppressed the expression of inducible nitric oxide synthase protein and mRNA.

  合成了类黄酮化合物作为抑制脂多糖激活的巨噬细胞系RAW 264.7细胞中一氧化氮产生的抑制剂。我们制备了比来自毛竹（Alpinia oxyphylla）的天然分子黄酮A和B更强的抑制剂。通过对类化合物的有限结构活性关系研究，我们得出结论：维持两个芳基之间的连接链的最佳长度以及连接链中存在烯酮基团对活性至关重要。最有效结构的IC50值为0.92μM。活性类化合物抑制了诱导型一氧化氮合酶蛋白及其mRNA的表达。
• Chain-Branched acyclic phenethylthiocarbamates as vanilloid receptor antagonists
  作者：JungWha Yoon、HyeYoung Choi、Hyun Joo Lee、Chong Hyun Ryu、Hyeung-geun Park、Young-ger Suh、Uhtaek Oh、Yeon Su Jeong、Jin Kyu Choi、Young-Ho Park、Hee-Doo Kim

  DOI：10.1016/s0960-894x(03)00178-1

  日期：2003.5

  A series of acyclic phenethylthiocarbamate derivatives have been synthesized, and their antagonist effect against vanilloid receptor tested. Chain branching led to a significant change in antagonist activity of the parent molecule. Ethyl-branched le showed a 6.3 muM Of IC50 value in Ca-45(2+)-influx assay. (C) 2003 Elsevier Science Ltd. All rights reserved.