(+/-)-5-hydroxy-7-(4'-hydroxyphenyl)-1-phenyl-3-heptanone | 83161-96-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (+/-)-5-hydroxy-7-(4'-hydroxyphenyl)-1-phenyl-3-heptanone
• 英文别名: 5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one
• CAS: 83161-96-0；529510-66-5
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: UNMNJFPAJOHXMT-UHFFFAOYSA-N

物化性质

• 沸点：
  523.7±45.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对羟基苯丙酸甲酯 在 lithium aluminium tetrahydride 、 水 、 sodium acetate 、 对甲苯磺酸 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (+/-)-5-hydroxy-7-(4'-hydroxyphenyl)-1-phenyl-3-heptanone
  参考文献：
  名称：

  摘要：

  (±)-5-羟基-1,7-双-(4'-羟基苯基)-3-庚酮 (2a)、(±)-5-羟基-1-(4'-羟基苯基)-7-苯基-3-庚酮 (2b)、(±)-5-羟基-7-(4'-羟基苯基)-1-苯基-3-庚酮 (2c) 和 (±)-5-羟基-1,7-双-(苯基)-3-庚酮 (2d) 已经被合成，用于研究在牛瘤胃液中体外消化抑制的结构-活性关系。这些化合物的活性与从 Betula pendula 分离出的具有手性 (S)-2a 及其苷 platyphylloside (1) 进行了比较。化合物 2a 的活性略低于 (S)-2a 和 platyphylloside，而 2b 和 2c 的活性更高，2d 的活性则低于 (S)-2a 和 platyphylloside。

  DOI：

  10.1023/a:1020847423427

文献信息

• Antiviral activity of diarylheptanoid stereoisomers against respiratory syncytial virus in vitro and in vivo
  作者：Katsuhiko Konno、Motofumi Miura、Masaharu Toriyama、Shigeyasu Motohashi、Rie Sawamura、Wataru Watanabe、Hiroki Yoshida、Masahiko Kato、Ryuichi Yamamoto、Ken Yasukawa、Masahiko Kurokawa

  DOI：10.1007/s11418-013-0743-6

  日期：2013.10

  We previously showed that (5S)-5-hydroxy-7-(4-hydroxyphenyl)-1-phenylhept-3-one (AO-0011) and (5S)-5-methoxy-1,7-diphenylhept-3-one (AO-0016) isolated from Alpinia officinarum exhibited stronger anti-influenza virus activity and anti-respiratory syncytial virus (RSV) activity, respectively, than the other isolated diarylheptanoids. In this study, we synthesized an enantiomer (AO-0503) and racemate (AO-0504) of AO-0011 and an enantiomer (AO-0514) of AO-0016. The anti-RSV activities of the three stereoisomers (AO-0503, AO-0504, and AO-0514) and AO-0011 were examined in vitro and in vivo to evaluate the stereoisomeric effect on anti-RSV activity. In a plaque reduction assay using human epidermoid carcinoma cells, all four diarylheptanoids significantly exhibited anti-RSV activity, and AO-0514 and AO-0016 exhibited stronger anti-RSV activity than AO-0503, AO-0504, and AO-0011. In a murine RSV infection model, all four diarylheptanoids with anti-RSV activity in vitro were also significantly effective in reducing virus titers in the lungs of RSV-infected mice. In the histopathological analysis of RSV-infected lungs, the oral administration of even AO-0514, which showed the lowest reduction of virus titers in the lungs, was significantly effective in reducing the infiltration of lymphocytes and in reducing the interferon-γ level, which is a marker of severity of pneumonia due to RSV infection, in bronchoalveolar lavage fluids prepared from RSV-infected mice. Although the stereoisomeric effects of diarylheptanoids on anti-RSV activity varied moderately, all four diarylheptanoids examined were suggested to ameliorate pneumonia and have a potential anti-RSV activity in vivo. They are possibly mother compounds for the development of an anti-RSV drug in the future.

  的影响，但AO-0514和AO-0016表现出更强的抗RSV活性。在用人类表皮癌细胞进行的斑块减少试验中，所有四种二芳基庚烷均表现出显著的抗RSV活性，并且AO-0514和AO-0016表现出比AO-0503、AO-0504和AO-0011更强的抗RSV活性。在小鼠RSV感染模型中，所有四种在体外具有抗RSV活性的二芳基庚烷在降低感染RSV的小鼠肺部病毒滴度方面也表现出显著的效果。在对感染RSV的肺部进行组织病理学分析时，口服给药甚至AO-0514（其在肺部病毒滴度降低方面表现最低）在降低淋巴细胞浸润和降低因RSV感染引起的肺炎严重程度的标志物——支气管肺泡灌洗液中的干扰素-γ水平方面也表现出显著的效果。尽管二芳基庚烷对抗RSV活性的立体异构体效应的影响，但AO-0514和AO-0016表现出更强的抗RSV活性。在用人类表皮癌细胞进行的斑块减少试验中，所有四种二芳基庚烷均表现出显著的抗RSV活性，并且AO-0514和AO-0016表现出比AO-0503、AO-0
• Kato, Nobuharu; Hamada, Yasumasa; Shioiri, Takayuki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 8, p. 3323 - 3326
  作者：Kato, Nobuharu、Hamada, Yasumasa、Shioiri, Takayuki

  DOI：——

  日期：——
• KATO, NOBUHARU;HAMADA, YASUMASA;SHIOIRI, TAKAYUKI, CHEM. AND PHARM. BULL., 1984, 32, N 8, 3323-3326
  作者：KATO, NOBUHARU、HAMADA, YASUMASA、SHIOIRI, TAKAYUKI

  DOI：——

  日期：——