3-hydroxy-4-oxo-2-phenyl-4H-chromene-5,7-diyl diacetate | 1265223-39-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-hydroxy-4-oxo-2-phenyl-4H-chromene-5,7-diyl diacetate
• 英文别名: progalangin；5,7-diacetoxy-3-hydroxyflavone；(5-Acetyloxy-3-hydroxy-4-oxo-2-phenylchromen-7-yl) acetate
• CAS: 1265223-39-9
• 化学式: C₁₉H₁₄O₇
• 分子量: 354.316
• InChiKey: UBSUFBFIBNHRPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  白杨素 在 吡啶 、 二甲基二环氧乙烷 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 159.0h， 生成 3-hydroxy-4-oxo-2-phenyl-4H-chromene-5,7-diyl diacetate
  参考文献：
  名称：

  [EN] APP SPECIFIC BACE INHIBITORS (ASBIs) AND USES THEREOF
  [FR] INHIBITEURS DE BACE SPÉCIFIQUES DE L'APP (ASBI) ET LEURS UTILISATIONS

  摘要：

  在某些实施例中，提供了特定于APP的BACE抑制剂（ASBI）以及其用途。在某些实施例中，提供了预防或延迟早期阿尔茨海默病症状和/或认知功能障碍的方法，以及改善早期阿尔茨海默病症状和/或认知功能障碍的一种或多种症状，或预防或延迟早期阿尔茨海默病症状或认知功能障碍发展为阿尔茨海默病的方法，其中该方法涉及向需要的受试者施用足以预防或延迟早期阿尔茨海默病认知功能障碍发作的APP特异性BACE抑制剂（ASBI）的剂量，和/或改善早期阿尔茨海默病认知功能障碍的一种或多种症状，和/或预防或延迟早期阿尔茨海默病认知功能障碍发展为阿尔茨海默病。在某些实施例中，ASBI是一种黄酮类化合物（例如，没药酮）或黄酮类化合物前药（例如，没药酮前药）。

  公开号：

  WO2013142370A1

文献信息

• APP SPECIFIC BACE INHIBITORS (ASBIs) AND USES THEREOF
  申请人：BUCK INSTITUTE FOR RESEARCH ON AGING

  公开号：US20150306122A1

  公开（公告）日：2015-10-29

  In certain embodiments APP-specific BACE inhibitors (ASBIs) are provided as well as uses thereof. In certain embodiments methods of preventing or delaying the onset of a pre-Alzheimer's condition and/or cognitive dysfunction, and/or ameliorating one or more symptoms of a pre-Alzheimer's condition and/or cognitive dysfunction, or preventing or delaying the progression of a pre-Alzheimer's condition or cognitive dysfunction to Alzheimer's disease are provided where the method involves administering to a subject in need thereof an APP specific BACE inhibitor (ASBI) in an amount sufficient to prevent or delay the onset of a pre-Alzheimer's cognitive dysfunction, and/or to ameliorate one or more symptoms of a pre-Alzheimer's cognitive dysfunction, and/or to prevent or delay the progression of a pre-Alzheimer's cognitive dysfunction to Alzheimer's disease. In certain embodiments the ASBI is a flavonoid (e.g. galangin) or flavonoid progrug (e.g., galangin prodrug).

  在某些实施例中，提供了特定于APP的BACE抑制剂（ASBI）及其用途。在某些实施例中，提供了预防或延迟早期阿尔茨海默病症状和/或认知功能障碍的方法，和/或改善早期阿尔茨海默病症状和/或认知功能障碍的一个或多个症状的方法，或者预防或延迟早期阿尔茨海默病症状或认知功能障碍的进展到阿尔茨海默病的方法，其中该方法涉及向需要该方法的受试者施用足够剂量的特定于APP的BACE抑制剂（ASBI），以预防或延迟早期阿尔茨海默病认知功能障碍的发生，并/或改善早期阿尔茨海默病认知功能障碍的一个或多个症状，并/或预防或延迟早期阿尔茨海默病认知功能障碍的进展到阿尔茨海默病。在某些实施例中，ASBI是一种黄酮类化合物（例如，没药黄素）或黄酮类前药（例如，没药黄素前药）。
• APP SPECIFIC BACE INHIBITORS (ASBIS) AND USES THEREOF
  申请人：Buck Institute for Research on Aging

  公开号：EP3607946A1

  公开（公告）日：2020-02-12

  In certain embodiments APP-specific BACE inhibitors (ASBIs) are provided as well as uses thereof. In certain embodiments methods of preventing or delaying the onset of a pre-Alzheimer's condition and/or cognitive dysfunction, and/or ameliorating one or more symptoms of a pre-Alzheimer's condition and/or cognitive dysfunction, or preventing or delaying the progression of a pre-Alzheimer's condition or cognitive dysfunction to Alzheimer's disease are provided where the method involves administering to a subject in need thereof an APP specific BACE inhibitor (ASBI) in an amount sufficient to prevent or delay the onset of a pre-Alzheimer's cognitive dysfunction, and/or to ameliorate one or more symptoms of a pre-Alzheimer's cognitive dysfunction, and/or to prevent or delay the progression of a pre-Alzheimer's cognitive dysfunction to Alzheimer's disease. In certain embodiments the ASBI is a flavonoid (e.g. galangin) or flavonoid progrug (e.g., galangin prodrug).

  在某些实施方案中，提供了APP特异性BACE抑制剂（ASBIs）及其用途。在某些实施方案中，提供了预防或延缓阿尔茨海默氏症前期症状和/或认知功能障碍的发生，和/或改善阿尔茨海默氏症前期症状和/或认知功能障碍的一种或多种症状，或预防或延缓阿尔茨海默氏症前期症状或认知功能障碍进展的方法、或预防或延缓阿尔茨海默氏症前期症状或认知功能障碍发展为阿尔茨海默氏症，其中所述方法包括向有需要的受试者施用APP特异性BACE抑制剂（ASBI），其用量足以预防或延缓阿尔茨海默氏症前期认知功能障碍的发生、和/或改善阿尔茨海默氏症前期认知功能障碍的一种或多种症状，和/或预防或延缓阿尔茨海默氏症前期认知功能障碍发展为阿尔茨海默氏症。在某些实施方案中，ASBI 是类黄酮（如高良姜素）或类黄酮原药（如高良姜素原药）。
• APP specific BACE inhibitors (ASBIs) and uses thereof
  申请人：BUCK INSTITUTE FOR RESEARCH ON AGING

  公开号：US10357508B2

  公开（公告）日：2019-07-23

  In certain embodiments APP-specific BACE inhibitors (ASBIs) are provided as well as uses thereof. In certain embodiments methods of preventing or delaying the onset of a pre-Alzheimer's condition and/or cognitive dysfunction, and/or ameliorating one or more symptoms of a pre-Alzheimer's condition and/or cognitive dysfunction, or preventing or delaying the progression of a pre-Alzheimer's condition or cognitive dysfunction to Alzheimer's disease are provided where the method involves administering to a subject in need thereof an APP specific BACE inhibitor (ASBI) in an amount sufficient to prevent or delay the onset of a pre-Alzheimer's cognitive dysfunction, and/or to ameliorate one or more symptoms of a pre-Alzheimer's cognitive dysfunction, and/or to prevent or delay the progression of a pre-Alzheimer's cognitive dysfunction to Alzheimer's disease. In certain embodiments the ASBI is a flavonoid (e.g. galangin) or flavonoid prodrug (e.g., galangin prodrug).

  在某些实施方案中，提供了APP特异性BACE抑制剂（ASBIs）及其用途。在某些实施方案中，提供了预防或延缓阿尔茨海默氏症前期症状和/或认知功能障碍的发生，和/或改善阿尔茨海默氏症前期症状和/或认知功能障碍的一种或多种症状，或预防或延缓阿尔茨海默氏症前期症状或认知功能障碍进展的方法、或预防或延缓阿尔茨海默氏症前期症状或认知功能障碍发展为阿尔茨海默氏症，其中所述方法包括向有需要的受试者施用APP特异性BACE抑制剂（ASBI），其用量足以预防或延缓阿尔茨海默氏症前期认知功能障碍的发生、和/或改善阿尔茨海默氏症前期认知功能障碍的一种或多种症状，和/或预防或延缓阿尔茨海默氏症前期认知功能障碍发展为阿尔茨海默氏症。在某些实施方案中，ASBI 是类黄酮（如高良姜素）或类黄酮原药（如高良姜素原药）。
• App specific BACE inhibitors (ASBIs) and uses thereof
  申请人：BUCK INSTITUTE FOR RESEARCH ON AGING

  公开号：US10835546B2

  公开（公告）日：2020-11-17

  In certain embodiments APP-specific BACE inhibitors (ASBIs) are provided as well as uses thereof. In certain embodiments methods of preventing delaying the onset of a pre-Alzheimer's condition and/or cognitive dysfunction, and/or ameliorating one or more symptoms of a pre-Alzheimer's condition and/or cognitive dysfunction, or preventing or delaying the progression of a pre-Alzheimer's condition or cognitive dysfunction to Alzheimer's disease are provided where the method involves administering to a subject in need thereof an APP specific BACE inhibitor (ASBI) in an amount sufficient to prevent or delay the onset of a pre-Alzheimer's cognitive dysfunction, and/or to ameliorate one or more symptoms of a pre-Alzheimer's cognitive dysfunction, and/or to prevent or delay the progression of a pre-Alzheimer's cognitive dysfunction to Alzheimer's disease. In certain embodiments the ASBI is a flavonoid (e.g. galangin) or flavonoid progrug (e.g., galangin prodrug).

  在某些实施方案中，提供了APP特异性BACE抑制剂（ASBIs）及其用途。在某些实施方案中，提供了预防延迟阿尔茨海默氏症前期症状和/或认知功能障碍的发生，和/或改善阿尔茨海默氏症前期症状和/或认知功能障碍的一种或多种症状，或预防或延迟阿尔茨海默氏症前期症状或认知功能障碍的进展的方法、或预防或延缓阿尔茨海默氏症前期症状或认知功能障碍发展为阿尔茨海默氏症，其中所述方法包括向有需要的受试者施用APP特异性BACE抑制剂（ASBI），其用量足以预防或延缓阿尔茨海默氏症前期认知功能障碍的发生、和/或改善阿尔茨海默氏症前期认知功能障碍的一种或多种症状，和/或预防或延缓阿尔茨海默氏症前期认知功能障碍发展为阿尔茨海默氏症。在某些实施方案中，ASBI 是类黄酮（如高良姜素）或类黄酮原药（如高良姜素原药）。
• Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane
  作者：Benjamin J. Compton、Lesley Larsen、Rex T. Weavers

  DOI：10.1016/j.tet.2010.11.076

  日期：2011.1

  The reaction of 5,7-dimethoxyflavone with dimethyldioxirane (DMDO) gives the 2,3-epoxide rapidly at first. However, low levels of ring A hydroxylated by-products are also formed. With increasing proportions of DMDO, demethylation at C-5 becomes apparent and consumption of substrate is not matched by further significant build-up of the epoxide. Deactivation of ring A by the use of acyl groups removes this complication. 5,7-Diacylflavones give excellent yields of epoxides and monoacyl derivatives also react in good yield. Ionization potential mans derived from density functional theory calculations (B3LYP/6-31G*), provide good visual indicators of the relative reactivity of the key nucleophilic loci. The epoxides may be isolated as such, or transformed into flavonols by treatment with p-toluenesulfonic acid. (C) 2010 Elsevier Ltd. All rights reserved.