6-<1-(3,4,5-trimethoxyphenyl)ethyl>-1,3-benzodioxol-5-ol | 109336-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-<1-(3,4,5-trimethoxyphenyl)ethyl>-1,3-benzodioxol-5-ol
• 英文别名: 1,3-Benzodioxol-5-ol, 6-[1-(3,4,5-trimethoxyphenyl)ethyl]-；6-[1-(3,4,5-trimethoxyphenyl)ethyl]-1,3-benzodioxol-5-ol
• CAS: 109336-12-1
• 化学式: C₁₈H₂₀O₆
• 分子量: 332.353
• InChiKey: IISFNAFZYSGNEP-UHFFFAOYSA-N

物化性质

• 熔点：
  130-131 °C(Solv: methanol (67-56-1))
• 沸点：
  475.2±45.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-<1-(3,4,5-trimethoxyphenyl)ethyl>-1,3-benzodioxol-5-ol 在 sodium tetrahydroborate 、 potassium carbonate 、 lithium chloride 作用下， 以 乙二醇二甲醚 、 丙酮 为溶剂， 反应 7.5h， 生成 2-[[6-[1-(3,4-Dimethoxyphenyl)ethyl]-1,3-benzodioxol-5-yl]oxy]ethanol
  参考文献：
  名称：

  In vivo antitumor activity of 6-benzyl-1,3-benzodioxole derivatives against the P388, L1210, B16, and M5076 murine models

  摘要：

  A series of 6-benzyl-1,3-benzodioxoles have been synthesized and evaluated against the in vivo ip P388 murine lymphocytic leukemia. Selected activities against this system were tested against the additional in vivo systems L1210, B16, M5076, and MX1. The most active of the 6-benzyl-1,3-benzodioxoles tested were as effective as podophyllotoxin as experimental antitumor agents in vivo, but larger doses were required. Three of the P388-active series members were active against the in vitro astrocytoma assay, which detects compounds that interfere with or bind to tubulin.

  DOI：

  10.1021/jm00393a012
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 在 sodium tetrahydroborate 、 草酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 6-<1-(3,4,5-trimethoxyphenyl)ethyl>-1,3-benzodioxol-5-ol
  参考文献：
  名称：

  In vivo antitumor activity of 6-benzyl-1,3-benzodioxole derivatives against the P388, L1210, B16, and M5076 murine models

  摘要：

  A series of 6-benzyl-1,3-benzodioxoles have been synthesized and evaluated against the in vivo ip P388 murine lymphocytic leukemia. Selected activities against this system were tested against the additional in vivo systems L1210, B16, M5076, and MX1. The most active of the 6-benzyl-1,3-benzodioxoles tested were as effective as podophyllotoxin as experimental antitumor agents in vivo, but larger doses were required. Three of the P388-active series members were active against the in vitro astrocytoma assay, which detects compounds that interfere with or bind to tubulin.

  DOI：

  10.1021/jm00393a012

文献信息

• JURD, LEONARD;NARAYANAN, V. L.;PAULL, KENNETH D., J. MED. CHEM., 30,(1987) N 10, 1752-1756
  作者：JURD, LEONARD、NARAYANAN, V. L.、PAULL, KENNETH D.

  DOI：——

  日期：——
• Methods, Agents, and Compositions for the Treatment of Acute Myeloid Leukemia
  申请人：University of Cincinnati

  公开号：US20220211669A1

  公开（公告）日：2022-07-07

  A method of treating a subject suffering from a condition characterized by over-expression of Ten-eleven translocation 1 (TET1) is provided, the method including administering to the subject an effective amount of a compound, or a pharmaceutically acceptable salt thereof, having the Formula I: wherein: R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from the group consisting of H, hydroxyl, alkyl, alkoxy, amine, halo, and trifluoromethyl, and wherein any two adjacent moieties of R 1 , R 2 , R 3 , R 4 , and R 5 may come together to form a heterocyclic ring; R 6 is H or hydroxyl; and R 7 is selected from H, wherein R 8 is C or O. Also provided are methods for selectively suppressing transcription of TET1 and/or reducing a level of 5-hydroxymethylcytosine in a subject by administering an effective amount of a Formula I compound and pharmaceutical compositions comprising Formula I compounds.
• In vivo antitumor activity of 6-benzyl-1,3-benzodioxole derivatives against the P388, L1210, B16, and M5076 murine models
  作者：Leonard Jurd、V. L. Narayanan、Kenneth D. Paull

  DOI：10.1021/jm00393a012

  日期：1987.10

  A series of 6-benzyl-1,3-benzodioxoles have been synthesized and evaluated against the in vivo ip P388 murine lymphocytic leukemia. Selected activities against this system were tested against the additional in vivo systems L1210, B16, M5076, and MX1. The most active of the 6-benzyl-1,3-benzodioxoles tested were as effective as podophyllotoxin as experimental antitumor agents in vivo, but larger doses were required. Three of the P388-active series members were active against the in vitro astrocytoma assay, which detects compounds that interfere with or bind to tubulin.