6-[(2-hydroxy-3-methoxyphenyl)(4-morpholinyl)methyl]-1,3-benzodioxol-5-ol | 187987-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-[(2-hydroxy-3-methoxyphenyl)(4-morpholinyl)methyl]-1,3-benzodioxol-5-ol
• 英文别名: 6-[(2-Hydroxy-3-methoxyphenyl)-morpholin-4-ylmethyl]-1,3-benzodioxol-5-ol
• CAS: 187987-85-5
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: DFFOLXUPFKVRIT-UHFFFAOYSA-N

物化性质

• 沸点：
  528.2±50.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[(2-hydroxy-3-methoxyphenyl)(4-morpholinyl)methyl]-1,3-benzodioxol-5-ol 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.25h， 生成 (6S,7S,8R)-8-(2-Hydroxy-3-methoxy-phenyl)-7-methyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromen-6-ol
  参考文献：
  名称：

  新型抗肿瘤药。2。苯并吡喃胺化合物

  摘要：

  1-3型吡咯烷，吗啉和哌啶衍生的曼尼希碱与丙酮，丙醛和丁醛反应形成4-8型2-甲基和3-甲基苯并吡喃。这些苯并吡喃的水解产生醇性苯并吡喃，其容易与多种胺，苯胺和肼衍生物缩合以形成9和10类型的各种异构体苯并吡喃。含有3,4,5-三甲氧基苯基环的苯并吡喃4-9是活性抗肿瘤剂，尤其是对人乳腺癌，中枢神经系统和结肠癌细胞系的抑制作用，这些肿瘤的总生长抑制作用通常在体外以低至10 -5 -10 -6摩尔/ 1。由于它们的体外活性和不寻常的结构，已选择了许多这类苯并吡喃用于体内异种移植物测试，以对抗乳腺癌和其他易感人类癌症。

  DOI：

  10.1002/jhet.5570330660
• 作为产物：
  描述：

  吗啉 、 芝麻酚 、 邻香草醛 以 甲醇 为溶剂， 反应 3.0h， 以72%的产率得到6-[(2-hydroxy-3-methoxyphenyl)(4-morpholinyl)methyl]-1,3-benzodioxol-5-ol
  参考文献：
  名称：

  新型抗肿瘤药。2。苯并吡喃胺化合物

  摘要：

  1-3型吡咯烷，吗啉和哌啶衍生的曼尼希碱与丙酮，丙醛和丁醛反应形成4-8型2-甲基和3-甲基苯并吡喃。这些苯并吡喃的水解产生醇性苯并吡喃，其容易与多种胺，苯胺和肼衍生物缩合以形成9和10类型的各种异构体苯并吡喃。含有3,4,5-三甲氧基苯基环的苯并吡喃4-9是活性抗肿瘤剂，尤其是对人乳腺癌，中枢神经系统和结肠癌细胞系的抑制作用，这些肿瘤的总生长抑制作用通常在体外以低至10 -5 -10 -6摩尔/ 1。由于它们的体外活性和不寻常的结构，已选择了许多这类苯并吡喃用于体内异种移植物测试，以对抗乳腺癌和其他易感人类癌症。

  DOI：

  10.1002/jhet.5570330660

文献信息

• Methods, agents, and compositions for the treatment of acute myeloid leukemia
  申请人：UNIVERSITY OF CINCINNATI

  公开号：US11311513B2

  公开（公告）日：2022-04-26

  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: R1, R2, R3, R4, and R5 are each independently selected from the group consisting of H, hydroxyl, alkyl, alkoxy, amine, halo, and trifluoromethyl, and wherein any two adjacent moieties of R1, R2, R3, R4, and R5 may come together to form a heterocyclic ring; R6 is H or hydroxyl; and R7 is selected from H, wherein R8 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.

  本发明提供了一种治疗以十-十一转位 1（TET1）过度表达为特征的疾病的方法，该方法包括向受试者施用有效量的具有式 I 的化合物或其药学上可接受的盐： 其中R1、R2、R3、R4 和 R5 各自独立地选自 H、羟基、烷基、烷氧基、胺、卤素和三氟甲基组成的组，其中 R1、R2、R3、R4 和 R5 的任意两个相邻分子可结合在一起形成杂环；R6 是 H 或羟基；R7 选自 H、 还提供了通过施用有效量的式Ⅰ化合物和包含式Ⅰ化合物的药物组合物来选择性抑制受试者体内 TET1 的转录和/或降低 5-羟甲基胞嘧啶水平的方法。
• METHODS, AGENTS, AND COMPOSITIONS FOR THE TREATMENT OF ACUTE MYELOID LEUKEMIA
  申请人：University of Cincinnati

  公开号：EP3615020A1

  公开（公告）日：2020-03-04
• 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.
• [EN] METHODS, AGENTS, AND COMPOSITIONS FOR THE TREATMENT OF ACUTE MYELOID LEUKEMIA<br/>[FR] MÉTHODES, AGENTS ET COMPOSITIONS DESTINÉS À TRAITER LA LEUCÉMIE AIGUË MYÉLOÏDE
  申请人：UNIV CINCINNATI

  公开号：WO2018200041A1

  公开（公告）日：2018-11-01

  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: (formula I) wherein: R1, R2, R3, R4, and R5 are each independently selected from the group consisting of H, hydroxyl, alkyl, alkoxy, amine, halo, and trifluoromethyl, and wherein any two adjacent moieties of R1, R2, R3, R4, and R5 may come together to form a heterocyclic ring; R6 is H or hydroxyl; and R7 is selected from H, (formula 2), and (formula 3), wherein R8 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.