6-[1-pyrrolidinyl(2,4,6-trimethoxyphenyl)methyl]-1,3-benzodioxol-5-ol | 116385-21-8

• 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-pyrrolidinyl(2,4,6-trimethoxyphenyl)methyl]-1,3-benzodioxol-5-ol
• 英文别名: 6-[Pyrrolidin-1-yl-(2,4,6-trimethoxyphenyl)methyl]-1,3-benzodioxol-5-ol
• CAS: 116385-21-8
• 化学式: C₂₁H₂₅NO₆
• 分子量: 387.433
• InChiKey: FADLEYWTWQECFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[1-pyrrolidinyl(2,4,6-trimethoxyphenyl)methyl]-1,3-benzodioxol-5-ol 在 oxonium 、 氢气 作用下， 生成 (7S,8S)-6-Methoxy-6,7-dimethyl-8-(2,4,6-trimethoxy-phenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene
  参考文献：
  名称：

  抗肿瘤药鬼臼毒素的生物活性杂环类似物

  摘要：

  3,4-亚甲基二氧基苯酚（sesamol）与吡咯烷和芳族醛缩合，生成4型曼尼希碱。曼尼希碱与酮类试剂容易反应形成吡咯烷基苯并吡喃衍生物，该衍生物为抗癌药鬼臼毒素的抗有丝分裂和生物活性杂环类似物提供了简单的途径。

  DOI：

  10.1002/jhet.5570250113
• 作为产物：
  描述：

  四氢吡咯 、 芝麻酚 、 2,4,6-三甲氧基苯甲醛 以 甲醇 为溶剂， 以66%的产率得到6-[1-pyrrolidinyl(2,4,6-trimethoxyphenyl)methyl]-1,3-benzodioxol-5-ol
  参考文献：
  名称：

  抗肿瘤药鬼臼毒素的生物活性杂环类似物

  摘要：

  3,4-亚甲基二氧基苯酚（sesamol）与吡咯烷和芳族醛缩合，生成4型曼尼希碱。曼尼希碱与酮类试剂容易反应形成吡咯烷基苯并吡喃衍生物，该衍生物为抗癌药鬼臼毒素的抗有丝分裂和生物活性杂环类似物提供了简单的途径。

  DOI：

  10.1002/jhet.5570250113

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。
• JURD, LEONARD, J. HETEROCYCL. CHEM., 25,(1988) N 1, 89-96
  作者：JURD, LEONARD

  DOI：——

  日期：——
• 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.